The influence of macrocyclic polyether constitution upon ammonium ion/crown ether recognition processes

Chemistry - A European Journal

Volumn 6, Issue 12, 2000, Pages 2274-2287

  Cantrill, Stuart J ^a   Fulton, David A ^a   Heiss, Aaron M ^a   Pease, Anthony R ^a   Stoddart, J Fraser ^a   White, Andrew J P ^b   Williams, David J ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Crown ethers; Hydrogen bonds; Rotaxanes; Secondary ammonium ions; Self assembly

Indexed keywords

AMMONIA; POLYETHER; ROTAXANE;

ARTICLE; COMPLEX FORMATION; CRYSTAL STRUCTURE; HYDROGEN BOND; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ANALYSIS;

EID: 0034674339     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20000616)6:12<2274::AID-CHEM2274>3.0.CO;2-2     Document Type: Article

References (140)

1. For in-depth and historical analyses of cation/crown ether complexation, see:a) J. S. Bradshaw, R. M. Izatt, A. V. Bordunov, C. Y. Zhu, J. K. Hathaway in Comprehensive Supramolecular Chemistry, Vol. 1 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, G. W. Gokel), Pergamon, Oxford, 1996, pp. 35-95; b) R. M. Izatt, K. Pawluk, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1995, 95, 2529-2586; c) R. M. Izatt, K. Pawluk, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1991, 91, 1721-2085; d) G. W. Gokel. Crown Ethers and Cryptands, The Royal Society of Chemistry, Cambridge, 1991, pp. 64-98; e) Cation Binding by Macrocycles, (Eds.: Y. Inoue, G. W. Gokel), Marcel Dekker, New York, 1990; f) F. Vögtle, E. Weber in Crown Ethers and Analogs (Eds.: S. Patai, Z. Rappoport), Wiley, 1989, pp. 207-304; g) I. Goldberg in Inclusion Compounds, Vol. 2 (Eds.: J. L. Atwood, J. E. D. Davies, D.D. MacNicol), Academic Press, London, 1984, pp. 261-335.
2. For in-depth and historical analyses of cation/crown ether complexation, see:a) J. S. Bradshaw, R. M. Izatt, A. V. Bordunov, C. Y. Zhu, J. K. Hathaway in Comprehensive Supramolecular Chemistry, Vol. 1 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, G. W. Gokel), Pergamon, Oxford, 1996, pp. 35-95; b) R. M. Izatt, K. Pawluk, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1995, 95, 2529-2586; c) R. M. Izatt, K. Pawluk, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1991, 91, 1721-2085; d) G. W. Gokel. Crown Ethers and Cryptands, The Royal Society of Chemistry, Cambridge, 1991, pp. 64-98; e) Cation Binding by Macrocycles, (Eds.: Y. Inoue, G. W. Gokel), Marcel Dekker, New York, 1990; f) F. Vögtle, E. Weber in Crown Ethers and Analogs (Eds.: S. Patai, Z. Rappoport), Wiley, 1989, pp. 207-304; g) I. Goldberg in Inclusion Compounds, Vol. 2 (Eds.: J. L. Atwood, J. E. D. Davies, D.D. MacNicol), Academic Press, London, 1984, pp. 261-335.
3. For in-depth and historical analyses of cation/crown ether complexation, see:a) J. S. Bradshaw, R. M. Izatt, A. V. Bordunov, C. Y. Zhu, J. K. Hathaway in Comprehensive Supramolecular Chemistry, Vol. 1 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, G. W. Gokel), Pergamon, Oxford, 1996, pp. 35-95; b) R. M. Izatt, K. Pawluk, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1995, 95, 2529-2586; c) R. M. Izatt, K. Pawluk, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1991, 91, 1721-2085; d) G. W. Gokel. Crown Ethers and Cryptands, The Royal Society of Chemistry, Cambridge, 1991, pp. 64-98; e) Cation Binding by Macrocycles, (Eds.: Y. Inoue, G. W. Gokel), Marcel Dekker, New York, 1990; f) F. Vögtle, E. Weber in Crown Ethers and Analogs (Eds.: S. Patai, Z. Rappoport), Wiley, 1989, pp. 207-304; g) I. Goldberg in Inclusion Compounds, Vol. 2 (Eds.: J. L. Atwood, J. E. D. Davies, D.D. MacNicol), Academic Press, London, 1984, pp. 261-335.
4. For in-depth and historical analyses of cation/crown ether complexation, see:a) J. S. Bradshaw, R. M. Izatt, A. V. Bordunov, C. Y. Zhu, J. K. Hathaway in Comprehensive Supramolecular Chemistry, Vol. 1 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, G. W. Gokel), Pergamon, Oxford, 1996, pp. 35-95; b) R. M. Izatt, K. Pawluk, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1995, 95, 2529-2586; c) R. M. Izatt, K. Pawluk, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1991, 91, 1721-2085; d) G. W. Gokel. Crown Ethers and Cryptands, The Royal Society of Chemistry, Cambridge, 1991, pp. 64-98; e) Cation Binding by Macrocycles, (Eds.: Y. Inoue, G. W. Gokel), Marcel Dekker, New York, 1990; f) F. Vögtle, E. Weber in Crown Ethers and Analogs (Eds.: S. Patai, Z. Rappoport), Wiley, 1989, pp. 207-304; g) I. Goldberg in Inclusion Compounds, Vol. 2 (Eds.: J. L. Atwood, J. E. D. Davies, D.D. MacNicol), Academic Press, London, 1984, pp. 261-335.
5. For in-depth and historical analyses of cation/crown ether complexation, see:a) J. S. Bradshaw, R. M. Izatt, A. V. Bordunov, C. Y. Zhu, J. K. Hathaway in Comprehensive Supramolecular Chemistry, Vol. 1 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, G. W. Gokel), Pergamon, Oxford, 1996, pp. 35-95; b) R. M. Izatt, K. Pawluk, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1995, 95, 2529-2586; c) R. M. Izatt, K. Pawluk, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1991, 91, 1721-2085; d) G. W. Gokel. Crown Ethers and Cryptands, The Royal Society of Chemistry, Cambridge, 1991, pp. 64-98; e) Cation Binding by Macrocycles, (Eds.: Y. Inoue, G. W. Gokel), Marcel Dekker, New York, 1990; f) F. Vögtle, E. Weber in Crown Ethers and Analogs (Eds.: S. Patai, Z. Rappoport), Wiley, 1989, pp. 207-304; g) I. Goldberg in Inclusion Compounds, Vol. 2 (Eds.: J. L. Atwood, J. E. D. Davies, D.D. MacNicol), Academic Press, London, 1984, pp. 261-335.
6. For in-depth and historical analyses of cation/crown ether complexation, see:a) J. S. Bradshaw, R. M. Izatt, A. V. Bordunov, C. Y. Zhu, J. K. Hathaway in Comprehensive Supramolecular Chemistry, Vol. 1 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, G. W. Gokel), Pergamon, Oxford, 1996, pp. 35-95; b) R. M. Izatt, K. Pawluk, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1995, 95, 2529-2586; c) R. M. Izatt, K. Pawluk, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1991, 91, 1721-2085; d) G. W. Gokel. Crown Ethers and Cryptands, The Royal Society of Chemistry, Cambridge, 1991, pp. 64-98; e) Cation Binding by Macrocycles, (Eds.: Y. Inoue, G. W. Gokel), Marcel Dekker, New York, 1990; f) F. Vögtle, E. Weber in Crown Ethers and Analogs (Eds.: S. Patai, Z. Rappoport), Wiley, 1989, pp. 207-304; g) I. Goldberg in Inclusion Compounds, Vol. 2 (Eds.: J. L. Atwood, J. E. D. Davies, D.D. MacNicol), Academic Press, London, 1984, pp. 261-335.
7. For in-depth and historical analyses of cation/crown ether complexation, see:a) J. S. Bradshaw, R. M. Izatt, A. V. Bordunov, C. Y. Zhu, J. K. Hathaway in Comprehensive Supramolecular Chemistry, Vol. 1 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, G. W. Gokel), Pergamon, Oxford, 1996, pp. 35-95; b) R. M. Izatt, K. Pawluk, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1995, 95, 2529-2586; c) R. M. Izatt, K. Pawluk, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1991, 91, 1721-2085; d) G. W. Gokel. Crown Ethers and Cryptands, The Royal Society of Chemistry, Cambridge, 1991, pp. 64-98; e) Cation Binding by Macrocycles, (Eds.: Y. Inoue, G. W. Gokel), Marcel Dekker, New York, 1990; f) F. Vögtle, E. Weber in Crown Ethers and Analogs (Eds.: S. Patai, Z. Rappoport), Wiley, 1989, pp. 207-304; g) I. Goldberg in Inclusion Compounds, Vol. 2 (Eds.: J. L. Atwood, J. E. D. Davies, D.D. MacNicol), Academic Press, London, 1984, pp. 261-335.
8. For some recent examples, see: a) A. Drljaca, M. J. Hardie, C. L. Raston, L. Spiccia, Chem. Eur. J. 1999, 5, 2295-2299; b) A. P. Marchand, H.-S. Chong, S. Alihodzic, W. H. Watson, S. G. Bodige, Tetrahedron 1999, 55, 9687-9696; c) H. Liu, S. Liu, L. Echegoyen, Chem. Commun. 1999, 1493-1494; d) S. Flink, F. C. J. M. van Veggel, D. N. Reinhoudt, J. Phys. Chem. B 1999, 103, 6515-6520; e) R. A. Bartsch, H.-S. Hwang, V. S. Talanov, G. G. Talanova, D. W. Purkiss, R. D. Rogers, J. Org. Chem. 1999, 64, 5341-5349.
9. For some recent examples, see: a) A. Drljaca, M. J. Hardie, C. L. Raston, L. Spiccia, Chem. Eur. J. 1999, 5, 2295-2299; b) A. P. Marchand, H.-S. Chong, S. Alihodzic, W. H. Watson, S. G. Bodige, Tetrahedron 1999, 55, 9687-9696; c) H. Liu, S. Liu, L. Echegoyen, Chem. Commun. 1999, 1493-1494; d) S. Flink, F. C. J. M. van Veggel, D. N. Reinhoudt, J. Phys. Chem. B 1999, 103, 6515-6520; e) R. A. Bartsch, H.-S. Hwang, V. S. Talanov, G. G. Talanova, D. W. Purkiss, R. D. Rogers, J. Org. Chem. 1999, 64, 5341-5349.
10. For some recent examples, see: a) A. Drljaca, M. J. Hardie, C. L. Raston, L. Spiccia, Chem. Eur. J. 1999, 5, 2295-2299; b) A. P. Marchand, H.-S. Chong, S. Alihodzic, W. H. Watson, S. G. Bodige, Tetrahedron 1999, 55, 9687-9696; c) H. Liu, S. Liu, L. Echegoyen, Chem. Commun. 1999, 1493-1494; d) S. Flink, F. C. J. M. van Veggel, D. N. Reinhoudt, J. Phys. Chem. B 1999, 103, 6515-6520; e) R. A. Bartsch, H.-S. Hwang, V. S. Talanov, G. G. Talanova, D. W. Purkiss, R. D. Rogers, J. Org. Chem. 1999, 64, 5341-5349.
11. For some recent examples, see: a) A. Drljaca, M. J. Hardie, C. L. Raston, L. Spiccia, Chem. Eur. J. 1999, 5, 2295-2299; b) A. P. Marchand, H.-S. Chong, S. Alihodzic, W. H. Watson, S. G. Bodige, Tetrahedron 1999, 55, 9687-9696; c) H. Liu, S. Liu, L. Echegoyen, Chem. Commun. 1999, 1493-1494; d) S. Flink, F. C. J. M. van Veggel, D. N. Reinhoudt, J. Phys. Chem. B 1999, 103, 6515-6520; e) R. A. Bartsch, H.-S. Hwang, V. S. Talanov, G. G. Talanova, D. W. Purkiss, R. D. Rogers, J. Org. Chem. 1999, 64, 5341-5349.
12. For some recent examples, see: a) A. Drljaca, M. J. Hardie, C. L. Raston, L. Spiccia, Chem. Eur. J. 1999, 5, 2295-2299; b) A. P. Marchand, H.-S. Chong, S. Alihodzic, W. H. Watson, S. G. Bodige, Tetrahedron 1999, 55, 9687-9696; c) H. Liu, S. Liu, L. Echegoyen, Chem. Commun. 1999, 1493-1494; d) S. Flink, F. C. J. M. van Veggel, D. N. Reinhoudt, J. Phys. Chem. B 1999, 103, 6515-6520; e) R. A. Bartsch, H.-S. Hwang, V. S. Talanov, G. G. Talanova, D. W. Purkiss, R. D. Rogers, J. Org. Chem. 1999, 64, 5341-5349.
13. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
14. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
15. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
16. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
17. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
18. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
19. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
20. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
21. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
22. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
23. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
24. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
25. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
26. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
27. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
28. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
29. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
30. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
31. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
32. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
33. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L.
34. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
35. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
36. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
37. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
38. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
39. In Pedersen's seminal paper (C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017-7036), he noted that primary alkylammonium ions form 1:1 complexes with dibenzo[18]crown-6 (DB18C6). This ground-breaking discovery subsequently spawned much research in the areas of host - guest and supramolecular chemistry. For examples spanning from Pedersen's day until the present, see: a) E. B. Kyba, K. Koga, L. R. Sousa, M. G. Siegel, D. J. Cram, J. Am. Chem. Soc. 1973, 95, 2692-2693; b) D. J. Cram, J. M. Cram Science 1974, 183, 803-809: c) T. L. Tarnowski, D. J. Cram, J. Chem. Soc., Chem. Commun. 1976, 661 - 663; d) J. M. Timko, S. S. Moore, D. M. Walba, P.C. Hiberty, D. J. Cram, J. Am. Chem. Soc. 1977, 99, 4207-4219; e) E. P. Kyba, J. M. Timko, L. J. Kaplan, F. de Jong, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1978, 100, 4558-4568; f) D. J. Cram, J. M. Cram Acc. Chem. Res. 1978, 11, 8-14; g) J. F. Stoddart, Chem. Soc. Rev. 1979, 8, 85-142; h) M. J. Bovill, D. J. Chadwick, M. R. Johnson, N. F. Jones, I. O. Sutherland, R. F. Newton, J. Chem. Soc., Chem. Commun. 1979, 1065-1066; i) J.-M. Lehn in IUPAC Frontiers of Chemistry, (Ed. K. J. Laidler), Pergamon, Oxford, 1982, pp. 265-272; j) I. Goldberg, J. Am. Chem. Soc. 1980, 102, 4106-4113; k) F. De Jong, D. N. Reinhoudt, Adv. Phys. Org. Chem. 1980, 17, 279-433. l) D. J. Cram, K. N. Trueblood, Top. Curr. Chem. 1981, 98, 43-106; m) J. S. Bradshaw, S. L. Baxter, J. D. Lamb, R. M. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1981, 103, 1821-1827; n) K. N. Trueblood, C. B. Knobler, D. S. Lawrence, R. V. Stevens, J. Am. Chem. Soc. 1982, 104, 1355-1362; o) R. Aldag, G. Schröder, Liebigs Ann. Chem. 1984, 1036-1045; p) I. O. Sutherland, Chem. Soc. Rev. 1986, 15, 63-91; q) J. F. Stoddart, Top. Stereochem. 1987, 17, 205-288: r) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020; s) S. Misumi, Pure Appl. Chem. 1990, 62, 493-498: t) I. O. Sutherland, Pure Appl. Chem. 499-504: u) R. M. Izatt, T. Wang, J. K. Hathaway, X. X. Zhang, J. C. Curtis, J. S. Bradshaw, C. Y. Zhu, P. Huszthy, J. Incl. Phenom. 1994, 17, 157-175; v) M. T. Reetz, J. Huff, J. Rudolph, K. Töllner, A. Deege, R. Goddard, J. Am. Chem. Soc. 1994, 116, 11588-11589; w) B. L. Williamson, C. S. Creaser, Int. J. Mass Spectrom. 1998, 188, 53-61; x) A. P. Hansson, P-O. Norrby, K. Wärnmark, Tetrahedron Lett. 1998, 39, 4565-4568; y) H. Tsukube, M. Wada, S. Shinoda, H. Tamiaki, Chem. Commun. 1999, 1007-1008.
40. a) P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. 1995, 107, 2001-2004; Angew Chem. Int. Ed. Engl. 1995, 34, 1869-1871:
41. a) P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. 1995, 107, 2001-2004; Angew Chem. Int. Ed. Engl. 1995, 34, 1869-1871:
42. b) P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 709-728:
43. c) P. T. Clink, C. Schiavo, J. F. Stoddart, D. J. Williams, Chem. Commun. 1996, 1483-1490:
44. d) P. R. Ashton, M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1997, 119, 12514-12524;
45. e) P. R. Ashton, M. C. T. Fyfe, M.-V. Martínez-Díaz, S. Menzer, C. Schiavo, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J. 1998, 4, 1523-1534;
46. f) M. Monlalti, L. Prodi, Chem. Commun. 1998, 1461-1462;
47. g) N. Yamaguchi, L. M. Hamilton, H.W. Gibson, Angew. Chem. 1998, 110, 3463-3466; Angew. Chem. Int. Ed. 1998, 37, 3275-3279;
48. g) N. Yamaguchi, L. M. Hamilton, H.W. Gibson, Angew. Chem. 1998, 110, 3463-3466; Angew. Chem. Int. Ed. 1998, 37, 3275-3279;
49. h) M. C. T. Fyfe, J. F. Stoddart, Adv. Supramol. Chem. 1999, 5, 1-53;
50. i) E. Ishow, A. Credi, V. Balzani, F. Spadola, L. Mandolini, Chem. Eur. J. 1999, 5, 984-989;
51. J) D. Fitzmaurice, S. N. Rao, J. A. Preece, J. F. Stoddart, S. Wenger, N. Zaccheroni, Angew. Chem. 1999, 111, 1220-1224: Angew. Chem. Int. Ed. 1999, 38, 1147-1150.
52. J) D. Fitzmaurice, S. N. Rao, J. A. Preece, J. F. Stoddart, S. Wenger, N. Zaccheroni, Angew. Chem. 1999, 111, 1220-1224: Angew. Chem. Int. Ed. 1999, 38, 1147-1150.
53. P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, S. Menzer, D. Philp, N. Spencer, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. 1995, 107, 1997-2001: Angew. Chem. Int. Ed. Engl. 1995, 34, 1865-1869.
54. P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, S. Menzer, D. Philp, N. Spencer, J. F. Stoddart, P. A. Tasker, D. J. Williams, Angew. Chem. 1995, 107, 1997-2001: Angew. Chem. Int. Ed. Engl. 1995, 34, 1865-1869.
55. Complexes formed between secondary dialkylammonium ions and crown ethers having less than 24 atoms in their macrorings have been observed to occur in a face-to-face manner. See: a) J. C. Metcalfe, J. F. Stoddart, G. Jones, J. Am. Chem. Soc: 1977, 99, 8317-8319: b) J. Krane, O. Aune, Acta Chem. Scand. Sect. B 1980, 34, 397-401; c) J. C. Metcalfe, J. F. Stoddart, G. Jones, A. Atkinson, I. S. Kerr, D. J. Williams, J. Chem. Soc. Chem. Commun. 1980, 540-543: d) S. S. Abed-Ali, B. J. Brisdon, R. England, J. Chem. Soc. Chem. Commun. 1987, 1565-1566.
56. Complexes formed between secondary dialkylammonium ions and crown ethers having less than 24 atoms in their macrorings have been observed to occur in a face-to-face manner. See: a) J. C. Metcalfe, J. F. Stoddart, G. Jones, J. Am. Chem. Soc: 1977, 99, 8317-8319: b) J. Krane, O. Aune, Acta Chem. Scand. Sect. B 1980, 34, 397-401; c) J. C. Metcalfe, J. F. Stoddart, G. Jones, A. Atkinson, I. S. Kerr, D. J. Williams, J. Chem. Soc. Chem. Commun. 1980, 540-543: d) S. S. Abed-Ali, B. J. Brisdon, R. England, J. Chem. Soc. Chem. Commun. 1987, 1565-1566.
57. Complexes formed between secondary dialkylammonium ions and crown ethers having less than 24 atoms in their macrorings have been observed to occur in a face-to-face manner. See: a) J. C. Metcalfe, J. F. Stoddart, G. Jones, J. Am. Chem. Soc: 1977, 99, 8317-8319: b) J. Krane, O. Aune, Acta Chem. Scand. Sect. B 1980, 34, 397-401; c) J. C. Metcalfe, J. F. Stoddart, G. Jones, A. Atkinson, I. S. Kerr, D. J. Williams, J. Chem. Soc. Chem. Commun. 1980, 540-543: d) S. S. Abed-Ali, B. J. Brisdon, R. England, J. Chem. Soc. Chem. Commun. 1987, 1565-1566.
58. Complexes formed between secondary dialkylammonium ions and crown ethers having less than 24 atoms in their macrorings have been observed to occur in a face-to-face manner. See: a) J. C. Metcalfe, J. F. Stoddart, G. Jones, J. Am. Chem. Soc: 1977, 99, 8317-8319: b) J. Krane, O. Aune, Acta Chem. Scand. Sect. B 1980, 34, 397-401; c) J. C. Metcalfe, J. F. Stoddart, G. Jones, A. Atkinson, I. S. Kerr, D. J. Williams, J. Chem. Soc. Chem. Commun. 1980, 540-543: d) S. S. Abed-Ali, B. J. Brisdon, R. England, J. Chem. Soc. Chem. Commun. 1987, 1565-1566.
59. a) A. G. Kolchinski, D. H. Busch, N. W. Alcock, J. Chem. Soc. Chem. Commun. 1995, 1289-1291:
60. b) P. R. Ashton, P. T. Glink, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 729-736:
61. c) M.-V. Martínez-Díaz, N. Spencer, J. F. Stoddart, Angew. Chem. 1997, 109, 1991-1994; Angew. Chem. Int. Ed. Engl. 1997, 36, 1904-1907;
62. c) M.-V. Martínez-Díaz, N. Spencer, J. F. Stoddart, Angew. Chem. 1997, 109, 1991-1994; Angew. Chem. Int. Ed. Engl. 1997, 36, 1904-1907;
63. d) P. R. Ashton, I. Baxter, M. C. T. Fyfe, F. M. Raymo, N. Spencer, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc, 1998, 120, 2297-2307;
64. e) P. R. Ashton, R. Ballardini, V. Balzani, I. Baxter, A. Credi, M. C. T. Fyfe, M. T. Gandolfi, M. Gómez-López, M.-V. Martínez-Díaz, A. Piersanti, N, Spencer, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1998, 120, 11932-11942;
65. f) A. G. Kolchinski, N. W. Alcock, R. A. Roesner, D. H. Busch, Chem. Commun. 1998, 1437-1438;
66. g) S. J. Canlrill, D. A. Fulton, M. C. T. Fyfe, J. F. Stoddart, A. J. P. White, D. J. Williams, Tetrahedron Lett. 1999, 40, 3669-3672;
67. h) S. J. Rowan, S. J. Cantrill, J. F. Stoddart, Org. Lett. 1999, 1, 129-132
68. i) S. J. Cantrill, M. C. T. Fyfe, A. M. Heiss, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Commun. 1999, 1251-1252;
69. J) T. Takata, H. Kawasaki, S. Asai, Y. Furusho, N. Kihara, Chem. Lett. 1999, 223-224:
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98. Our investigations (P. R. Ashton, I. Baxter, S. J. Cantrill, M. C. T. Fyfe, P. T. Glink, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 1344-1347, Angew. Chem. Int. Ed. 1998, 37, 1294-1297) on a self-complementary 'daisy-chain' system - in which a secondary dialkylammonium ion-containing side chain is appended to one of the catechol residues of a DB24C8 framework - revealed that, upon oligo/polymerization, numerous stereoisomeric super-structures can be formed. It was immediately apparent that this complication could be circumvented by designing a compound in which the ammonium ion substituted catechol ring of the DB24C8 macrocycle is replaced by a resorcinol ring which carries the ammonium ion side-chain attached to its C-5 position. Such a 'mutation' of the monomer, although simplifying symmetry situation, has the implication of expanding the macroring from 24 to 25 atoms, thus raising the question - are crown ethers with a 25C8 constitution effective hosts for secondary dialkylammonium ions?
99. Our investigations (P. R. Ashton, I. Baxter, S. J. Cantrill, M. C. T. Fyfe, P. T. Glink, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 1998, 110, 1344-1347, Angew. Chem. Int. Ed. 1998, 37, 1294-1297) on a self-complementary 'daisy-chain' system - in which a secondary dialkylammonium ion-containing side chain is appended to one of the catechol residues of a DB24C8 framework - revealed that, upon oligo/polymerization, numerous stereoisomeric super-structures can be formed. It was immediately apparent that this complication could be circumvented by designing a compound in which the ammonium ion substituted catechol ring of the DB24C8 macrocycle is replaced by a resorcinol ring which carries the ammonium ion side-chain attached to its C-5 position. Such a 'mutation' of the monomer, although simplifying symmetry situation, has the implication of expanding the macroring from 24 to 25 atoms, thus raising the question - are crown ethers with a 25C8 constitution effective hosts for secondary dialkylammonium ions?
100. For examples of interlocked macromolecules, see:a)F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643-1663; b) A. Harada, M. Okada, Y. Kawaguchi, M. Kamachi, Polym. Advan. Technol. 1999, 10, 3-12; c) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Kohler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851; d) D. Muscat, W. Köhler, H. J. Räder, K. Martin, S. Mullins, B. Müller, K. Müllen, Y. Geerts, Macromolecules 1999, 32, 1737-1745: e) K. M. Park, J. Heo, S. G. Roh, Y. M. Jeon, D. Whang, K. Kim, Mol. Cryst. Liq. Crys. A 1999, 327, 65-70; f) T. Takata, H. Kawasaki, A. Asai, N. Kihara, Y. Furusho, Chem. Lett. 1999, 111-112; g) C. Hamers, O. Kocian, F. M. Raymo, J. F. Stoddart, Adv. Mater. 1998, 10, 1366-1369: h) C. G. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; i) W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36, 2511-2514; j) H. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843-945.
101. For examples of interlocked macromolecules, see:a)F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643-1663; b) A. Harada, M. Okada, Y. Kawaguchi, M. Kamachi, Polym. Advan. Technol. 1999, 10, 3-12; c) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Kohler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851; d) D. Muscat, W. Köhler, H. J. Räder, K. Martin, S. Mullins, B. Müller, K. Müllen, Y. Geerts, Macromolecules 1999, 32, 1737-1745: e) K. M. Park, J. Heo, S. G. Roh, Y. M. Jeon, D. Whang, K. Kim, Mol. Cryst. Liq. Crys. A 1999, 327, 65-70; f) T. Takata, H. Kawasaki, A. Asai, N. Kihara, Y. Furusho, Chem. Lett. 1999, 111-112; g) C. Hamers, O. Kocian, F. M. Raymo, J. F. Stoddart, Adv. Mater. 1998, 10, 1366-1369: h) C. G. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; i) W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36, 2511-2514; j) H. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843-945.
102. For examples of interlocked macromolecules, see:a)F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643-1663; b) A. Harada, M. Okada, Y. Kawaguchi, M. Kamachi, Polym. Advan. Technol. 1999, 10, 3-12; c) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Kohler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851; d) D. Muscat, W. Köhler, H. J. Räder, K. Martin, S. Mullins, B. Müller, K. Müllen, Y. Geerts, Macromolecules 1999, 32, 1737-1745: e) K. M. Park, J. Heo, S. G. Roh, Y. M. Jeon, D. Whang, K. Kim, Mol. Cryst. Liq. Crys. A 1999, 327, 65-70; f) T. Takata, H. Kawasaki, A. Asai, N. Kihara, Y. Furusho, Chem. Lett. 1999, 111-112; g) C. Hamers, O. Kocian, F. M. Raymo, J. F. Stoddart, Adv. Mater. 1998, 10, 1366-1369: h) C. G. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; i) W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36, 2511-2514; j) H. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843-945.
103. For examples of interlocked macromolecules, see:a)F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643-1663; b) A. Harada, M. Okada, Y. Kawaguchi, M. Kamachi, Polym. Advan. Technol. 1999, 10, 3-12; c) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Kohler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851; d) D. Muscat, W. Köhler, H. J. Räder, K. Martin, S. Mullins, B. Müller, K. Müllen, Y. Geerts, Macromolecules 1999, 32, 1737-1745: e) K. M. Park, J. Heo, S. G. Roh, Y. M. Jeon, D. Whang, K. Kim, Mol. Cryst. Liq. Crys. A 1999, 327, 65-70; f) T. Takata, H. Kawasaki, A. Asai, N. Kihara, Y. Furusho, Chem. Lett. 1999, 111-112; g) C. Hamers, O. Kocian, F. M. Raymo, J. F. Stoddart, Adv. Mater. 1998, 10, 1366-1369: h) C. G. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; i) W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36, 2511-2514; j) H. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843-945.
104. For examples of interlocked macromolecules, see:a)F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643-1663; b) A. Harada, M. Okada, Y. Kawaguchi, M. Kamachi, Polym. Advan. Technol. 1999, 10, 3-12; c) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Kohler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851; d) D. Muscat, W. Köhler, H. J. Räder, K. Martin, S. Mullins, B. Müller, K. Müllen, Y. Geerts, Macromolecules 1999, 32, 1737-1745: e) K. M. Park, J. Heo, S. G. Roh, Y. M. Jeon, D. Whang, K. Kim, Mol. Cryst. Liq. Crys. A 1999, 327, 65-70; f) T. Takata, H. Kawasaki, A. Asai, N. Kihara, Y. Furusho, Chem. Lett. 1999, 111-112; g) C. Hamers, O. Kocian, F. M. Raymo, J. F. Stoddart, Adv. Mater. 1998, 10, 1366-1369: h) C. G. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; i) W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36, 2511-2514; j) H. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843-945.
105. For examples of interlocked macromolecules, see:a)F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643-1663; b) A. Harada, M. Okada, Y. Kawaguchi, M. Kamachi, Polym. Advan. Technol. 1999, 10, 3-12; c) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Kohler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851; d) D. Muscat, W. Köhler, H. J. Räder, K. Martin, S. Mullins, B. Müller, K. Müllen, Y. Geerts, Macromolecules 1999, 32, 1737-1745: e) K. M. Park, J. Heo, S. G. Roh, Y. M. Jeon, D. Whang, K. Kim, Mol. Cryst. Liq. Crys. A 1999, 327, 65-70; f) T. Takata, H. Kawasaki, A. Asai, N. Kihara, Y. Furusho, Chem. Lett. 1999, 111-112; g) C. Hamers, O. Kocian, F. M. Raymo, J. F. Stoddart, Adv. Mater. 1998, 10, 1366-1369: h) C. G. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; i) W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36, 2511-2514; j) H. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843-945.
106. For examples of interlocked macromolecules, see:a)F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643-1663; b) A. Harada, M. Okada, Y. Kawaguchi, M. Kamachi, Polym. Advan. Technol. 1999, 10, 3-12; c) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Kohler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851; d) D. Muscat, W. Köhler, H. J. Räder, K. Martin, S. Mullins, B. Müller, K. Müllen, Y. Geerts, Macromolecules 1999, 32, 1737-1745: e) K. M. Park, J. Heo, S. G. Roh, Y. M. Jeon, D. Whang, K. Kim, Mol. Cryst. Liq. Crys. A 1999, 327, 65-70; f) T. Takata, H. Kawasaki, A. Asai, N. Kihara, Y. Furusho, Chem. Lett. 1999, 111-112; g) C. Hamers, O. Kocian, F. M. Raymo, J. F. Stoddart, Adv. Mater. 1998, 10, 1366-1369: h) C. G. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; i) W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36, 2511-2514; j) H. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843-945.
107. For examples of interlocked macromolecules, see:a)F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643-1663; b) A. Harada, M. Okada, Y. Kawaguchi, M. Kamachi, Polym. Advan. Technol. 1999, 10, 3-12; c) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Kohler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851; d) D. Muscat, W. Köhler, H. J. Räder, K. Martin, S. Mullins, B. Müller, K. Müllen, Y. Geerts, Macromolecules 1999, 32, 1737-1745: e) K. M. Park, J. Heo, S. G. Roh, Y. M. Jeon, D. Whang, K. Kim, Mol. Cryst. Liq. Crys. A 1999, 327, 65-70; f) T. Takata, H. Kawasaki, A. Asai, N. Kihara, Y. Furusho, Chem. Lett. 1999, 111-112; g) C. Hamers, O. Kocian, F. M. Raymo, J. F. Stoddart, Adv. Mater. 1998, 10, 1366-1369: h) C. G. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; i) W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36, 2511-2514; j) H. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843-945.
108. For examples of interlocked macromolecules, see:a)F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643-1663; b) A. Harada, M. Okada, Y. Kawaguchi, M. Kamachi, Polym. Advan. Technol. 1999, 10, 3-12; c) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Kohler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851; d) D. Muscat, W. Köhler, H. J. Räder, K. Martin, S. Mullins, B. Müller, K. Müllen, Y. Geerts, Macromolecules 1999, 32, 1737-1745: e) K. M. Park, J. Heo, S. G. Roh, Y. M. Jeon, D. Whang, K. Kim, Mol. Cryst. Liq. Crys. A 1999, 327, 65-70; f) T. Takata, H. Kawasaki, A. Asai, N. Kihara, Y. Furusho, Chem. Lett. 1999, 111-112; g) C. Hamers, O. Kocian, F. M. Raymo, J. F. Stoddart, Adv. Mater. 1998, 10, 1366-1369: h) C. G. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; i) W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36, 2511-2514; j) H. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843-945.
109. For examples of interlocked macromolecules, see:a)F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643-1663; b) A. Harada, M. Okada, Y. Kawaguchi, M. Kamachi, Polym. Advan. Technol. 1999, 10, 3-12; c) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Kohler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851; d) D. Muscat, W. Köhler, H. J. Räder, K. Martin, S. Mullins, B. Müller, K. Müllen, Y. Geerts, Macromolecules 1999, 32, 1737-1745: e) K. M. Park, J. Heo, S. G. Roh, Y. M. Jeon, D. Whang, K. Kim, Mol. Cryst. Liq. Crys. A 1999, 327, 65-70; f) T. Takata, H. Kawasaki, A. Asai, N. Kihara, Y. Furusho, Chem. Lett. 1999, 111-112; g) C. Hamers, O. Kocian, F. M. Raymo, J. F. Stoddart, Adv. Mater. 1998, 10, 1366-1369: h) C. G. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; i) W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36, 2511-2514; j) H. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843-945.
110. For examples of interlocked macromolecules, see:a)F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643-1663; b) A. Harada, M. Okada, Y. Kawaguchi, M. Kamachi, Polym. Advan. Technol. 1999, 10, 3-12; c) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Kohler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851; d) D. Muscat, W. Köhler, H. J. Räder, K. Martin, S. Mullins, B. Müller, K. Müllen, Y. Geerts, Macromolecules 1999, 32, 1737-1745: e) K. M. Park, J. Heo, S. G. Roh, Y. M. Jeon, D. Whang, K. Kim, Mol. Cryst. Liq. Crys. A 1999, 327, 65-70; f) T. Takata, H. Kawasaki, A. Asai, N. Kihara, Y. Furusho, Chem. Lett. 1999, 111-112; g) C. Hamers, O. Kocian, F. M. Raymo, J. F. Stoddart, Adv. Mater. 1998, 10, 1366-1369: h) C. G. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; i) W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36, 2511-2514; j) H. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843-945.
111. For examples of interlocked macromolecules, see:a)F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643-1663; b) A. Harada, M. Okada, Y. Kawaguchi, M. Kamachi, Polym. Advan. Technol. 1999, 10, 3-12; c) J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, D. Muscat, S. Mullins, W. Kohler, C. Rosenauer, H. J. Räder, K. Martin, Y. Geerts, Chem. Eur. J. 1999, 5, 1841-1851; d) D. Muscat, W. Köhler, H. J. Räder, K. Martin, S. Mullins, B. Müller, K. Müllen, Y. Geerts, Macromolecules 1999, 32, 1737-1745: e) K. M. Park, J. Heo, S. G. Roh, Y. M. Jeon, D. Whang, K. Kim, Mol. Cryst. Liq. Crys. A 1999, 327, 65-70; f) T. Takata, H. Kawasaki, A. Asai, N. Kihara, Y. Furusho, Chem. Lett. 1999, 111-112; g) C. Hamers, O. Kocian, F. M. Raymo, J. F. Stoddart, Adv. Mater. 1998, 10, 1366-1369: h) C. G. Gong, H. W. Gibson, Angew. Chem. 1998, 110, 323-327; Angew. Chem. Int. Ed. 1998, 37, 310-314; i) W. Herrmann, M. Schneider, G. Wenz, Angew. Chem. 1997, 109, 2618-2621; Angew. Chem. Int. Ed. Engl. 1997, 36, 2511-2514; j) H. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843-945.
112. Gibson and co-workers (W. S. Bryant, I. A. Guzei, A. L. Rheingold, J. S. Merola, H.W. Gibson, J. Org. Chem. 1998, 63, 7634-7639) comment on the symmetrical nature of bis-meta-phenylene-containing crown ethers when they are incorporated into polymeric interlocked systems.
113. M. S. Newman, L. F. Lee, J. Org. Chem. 1972, 37, 4468-4469
114. H. G. McFadden, J. N. Phillips, Z. Naturforsch, C: Biosci. 1990, 45, 196-206.
115. a values-that the crown ether prefers to reside around the dialkylammonium center, rather than around the urea moiety.
116. 2- resonance. However, based upon the patterns observed for the β and γ protons, it is not unreasonable to suppose, by analogy, that selective through-space interactions also occur for the α protons.
117. I. J. A. Mertens, R. Wegh, L. W. Jenneskens, E. J. Vlietstra, A. van der Kerk-van Hoof, J. W. Zwikker, T. J. Cleij, W. J. J. Smeets, N. Veldman, A. L. Spek, J. Chem. Soc: Perkin Trans. 2 1998, 725-735.
118. + (the base peak), implying that there is an interaction more enduring than a simple face-to-face association, that is, the threading of the cation through the macroring of DB24C8, resulting in the formation of a [2]pseudorotaxane in the gas phase.
119. For leading references related to this method, see: J. C. Adrian, C. S. Wilcox, J. Am. Chem. Soc. 1991, 113, 678-680.
120. For leading references, see: a) K. A. Connors, Binding Constants, Wiley, New York, 1987 ; b) H. Tsukube, H. Furuta, A. Odani, Y. Takeda, Y. Kudo, Y. Inoue, Y. Liu, H. Sakamoto, K. Kimura in Comprehensive Supramolecular Chemistry, Vol. 8 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, J. A. Ripmeester), Pergamon, Oxford, 1996, pp. 425-482 and references therein.
121. For leading references, see: a) K. A. Connors, Binding Constants, Wiley, New York, 1987 ; b) H. Tsukube, H. Furuta, A. Odani, Y. Takeda, Y. Kudo, Y. Inoue, Y. Liu, H. Sakamoto, K. Kimura in Comprehensive Supramolecular Chemistry, Vol. 8 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, J. A. Ripmeester), Pergamon, Oxford, 1996, pp. 425-482 and references therein.
122. P. R. Ashton, R. A. Bartsch, S. J. Cantrill, R. E. Hanes, Jr., S. K. Hickingbottom, J. N. Lowe, J. A. Preece, J. F. Stoddart, V. S. Talanov, Z.-H. Wang, Tetrahedron Lett. 1999, 40, 3661-3664.
123. 6.
124. -1.
125. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caulfield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440-467.
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128. W. C. Still, A, Tempczyk, R. C. Hawley, T. Hendrickson, J. Am. Chem. Soc. 1990, 112, 6127-6129.
129. One of the earliest syntheses of bismetaphenyl-ene[26]crown-8 (sometimes referred to as dibenzo[26]-crown-8 (DB26C8)) was reported (G. Lindsten, O. Wennerström, R. Isaksson, J. Org. Chem. 1987, 52, 547-554) well over 10 years ago now. Subsequently, this compound was employed in the construction of an ion-selective electrode for the potentiometric sensing of guanidinium ions. See: F. N. Assubaie, G. J. Moody, J. D. R. Thomas, Analyst 1989, 114, 1545-1550. However, during the 1990s, three research groups have independently solved the X-ray crystal structure of this crown ether: the structural parameters reported by each group are, within experimental error, the same. See: i)E. Luboch, M.S. Fonar, Y. A. Siminov, V. K. Bel'sky, J. Biernat, Izv. Akad. Nauk, Ser. Khim. 1995, 2458-2464, ii) G. W. Buchanan, M. Lefort, A. Moghimi, C. Bensimon, J. Mol. Struct. 1997, 415, 267-275, and iii) H. W. Gibson et. al. see ref.
130. One of the earliest syntheses of bismetaphenyl-ene[26]crown-8 (sometimes referred to as dibenzo[26]-crown-8 (DB26C8)) was reported (G. Lindsten, O. Wennerström, R. Isaksson, J. Org. Chem. 1987, 52, 547-554) well over 10 years ago now. Subsequently, this compound was employed in the construction of an ion-selective electrode for the potentiometric sensing of guanidinium ions. See: F. N. Assubaie, G. J. Moody, J. D. R. Thomas, Analyst 1989, 114, 1545-1550. However, during the 1990s, three research groups have independently solved the X-ray crystal structure of this crown ether: the structural parameters reported by each group are, within experimental error, the same. See: i)E. Luboch, M.S. Fonar, Y. A. Siminov, V. K. Bel'sky, J. Biernat, Izv. Akad. Nauk, Ser. Khim. 1995, 2458-2464, ii) G. W. Buchanan, M. Lefort, A. Moghimi, C. Bensimon, J. Mol. Struct. 1997, 415, 267-275, and iii) H. W. Gibson et. al. see ref.
131. One of the earliest syntheses of bismetaphenyl-ene[26]crown-8 (sometimes referred to as dibenzo[26]-crown-8 (DB26C8)) was reported (G. Lindsten, O. Wennerström, R. Isaksson, J. Org. Chem. 1987, 52, 547-554) well over 10 years ago now. Subsequently, this compound was employed in the construction of an ion-selective electrode for the potentiometric sensing of guanidinium ions. See: F. N. Assubaie, G. J. Moody, J. D. R. Thomas, Analyst 1989, 114, 1545-1550. However, during the 1990s, three research groups have independently solved the X-ray crystal structure of this crown ether: the structural parameters reported by each group are, within experimental error, the same. See: i)E. Luboch, M.S. Fonar, Y. A. Siminov, V. K. Bel'sky, J. Biernat, Izv. Akad. Nauk, Ser. Khim. 1995, 2458-2464, ii) G. W. Buchanan, M. Lefort, A. Moghimi, C. Bensimon, J. Mol. Struct. 1997, 415, 267-275, and iii) H. W. Gibson et. al. see ref.
132. One of the earliest syntheses of bismetaphenyl-ene[26]crown-8 (sometimes referred to as dibenzo[26]-crown-8 (DB26C8)) was reported (G. Lindsten, O. Wennerström, R. Isaksson, J. Org. Chem. 1987, 52, 547-554) well over 10 years ago now. Subsequently, this compound was employed in the construction of an ion-selective electrode for the potentiometric sensing of guanidinium ions. See: F. N. Assubaie, G. J. Moody, J. D. R. Thomas, Analyst 1989, 114, 1545-1550. However, during the 1990s, three research groups have independently solved the X-ray crystal structure of this crown ether: the structural parameters reported by each group are, within experimental error, the same. See: i)E. Luboch, M.S. Fonar, Y. A. Siminov, V. K. Bel'sky, J. Biernat, Izv. Akad. Nauk, Ser. Khim. 1995, 2458-2464, ii) G. W. Buchanan, M. Lefort, A. Moghimi, C. Bensimon, J. Mol. Struct. 1997, 415, 267-275, and iii) H. W. Gibson et. al. see ref.
133. One of the earliest syntheses of bismetaphenyl-ene[26]crown-8 (sometimes referred to as dibenzo[26]-crown-8 (DB26C8)) was reported (G. Lindsten, O. Wennerström, R. Isaksson, J. Org. Chem. 1987, 52, 547-554) well over 10 years ago now. Subsequently, this compound was employed in the construction of an ion-selective electrode for the potentiometric sensing of guanidinium ions. See: F. N. Assubaie, G. J. Moody, J. D. R. Thomas, Analyst 1989, 114, 1545-1550. However, during the 1990s, three research groups have independently solved the X-ray crystal structure of this crown ether: the structural parameters reported by each group are, within experimental error, the same. See: i)E. Luboch, M.S. Fonar, Y. A. Siminov, V. K. Bel'sky, J. Biernat, Izv. Akad. Nauk, Ser. Khim. 1995, 2458-2464, ii) G. W. Buchanan, M. Lefort, A. Moghimi, C. Bensimon, J. Mol. Struct. 1997, 415, 267-275, and iii) H. W. Gibson et. al. see ref.
134. Interestingly, in neither of the latter papers is any mention made of the earlier X-ray crystallographic analyses. In only one paper, namely iii). is an earlier report of the synthesis of BMP26C8 acknowledged !
135. + and BMP26C8. No peaks were observed for any complexes formed between these two components, suggesting that a [2]pseudorotaxane does not exist under the conditions employed during this particular analysis.
136. A. Derome, M. Williamson, J. Mag. Reson. 1990, 88, 177-185.
137. a) A. Bax, D. G. Davis, J. Mag. Reson. 1985, 63, 207-213;
138. b) T. Hwang, A. J. Shaka, J. Am. Chem. Soc. 1992, 114, 3157-3159.
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140. SHELXTL PC version 5.03, Siemens Analytical X-Ray Instruments, Inc., Madison, WI, 1994.