Diastereoselective formation of host - Guest complexes between a series of phosphate-bridged cavitands and alkyl- and arylammonium ions studied by liquid secondary-ion mass spectrometry

Chemistry - A European Journal

Volumn 7, Issue 9, 2001, Pages 2034-2042

  Irico, Alessandra ^a   Vincenti, Marco ^a   Dalcanale, Enrico ^b  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

Cavitands; Diastereomers; Host guest systems; Hydrogen bonds; Mass spectrometry

Indexed keywords

HYDROGEN BONDS; ISOMERS; PH EFFECTS; PHOSPHATES; PROTONS; SECONDARY ION MASS SPECTROMETRY; THERMODYNAMICS;

DIASTEREOMERS;

IONS;

3 NITROBENZYL ALCOHOL; ALCOHOL DERIVATIVE; AMMONIUM DERIVATIVE; PHOSPHORUS DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; DIASTEREOISOMER; HYDROGEN BOND; MASS SPECTROMETRY; REACTION ANALYSIS; SYNTHESIS; THERMODYNAMICS;

EID: 0035805310     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010504)7:9<2034::AID-CHEM2034>3.0.CO;2-J     Document Type: Article

References (74)

1. a) Host - Guest Complex Chemistry: Macrocycles (Eds.: F. Vögtle, E. Weber), Springer, New York, 1988;
2. b) Inclusion Phenomena and Molecular Recognition (Ed.: J. L. Atwood), Plenum, New York, 1988;
3. c) D. J. Cram, J. M. Cram in Container Molecules and Their Guests (Ed.: J. F. Stoddard), Royal Society of Chemistry, London, 1994;
4. d) Comprehensive Supramolecular Chemistry, Vols. 1 and 2 (Eds.: J.-M. Lehn, J. L. Atwood, J. E. D. Davies, D. D. MacNicol, G. W. Gokel, F. Vögtle), Pergamon, Oxford, 1996.
5. M. Vincenti, A. Irico, E. Dalcanale in Advances in Mass Spectrometry, Vol. 14 (Eds.: E. J. Karijalainen, A. E. Hesso, J. E. Jalanen, U. P. Karijalainen), Elsevier Science, Amsterdam, 1998, pp. 129-150.
6. a) M. Vincenti, J. Mass Spectrum. 1995, 30, 925-939;
7. b) J. S. Brodbelt, D. V. Dearden, in Mass Spectrometry, Comprehensive Supramolecular Chemistry, Vol. 8 (Eds.: J. E. D. Davies, J. A. Ripmeester), Pergamon. Oxford, 1996;
8. c) K. Wang, G. W. Gokel, Pure Appl. Chem. 1996, 68, 1267-1272;
9. d) C. A. Schalley, Int. J. Mass Spectrom. 2000, 194, 11-39,
10. a) T. Lippmann, H. Wilde, M. Pinke, A. Schäfer, M. Hesse, G. Mann, Angew. Chem. 1993, 105, 1258-1260; Angew. Chem. Int. Ed. Engl. 1993, 32, 1195-1197;
11. a) T. Lippmann, H. Wilde, M. Pinke, A. Schäfer, M. Hesse, G. Mann, Angew. Chem. 1993, 105, 1258-1260; Angew. Chem. Int. Ed. Engl. 1993, 32, 1195-1197;
12. b) N. J. Haskins, M. R. Saunders, P. Camilleri, Rapid Commun. Mass Spectrom. 1994, 8, 423-426;
13. c) R. Colton, S. Mitchell, J. C. Traeger, Inorg. Chim. Acta 1995, 231, 87-93;
14. d) K. Wang, G. W. Gokel, J. Org. Chem. 1996, 61, 4693-4697;
15. e) D.-S. Young, H.-Y Hung, E. L. Kao, Rapid Commun. Mass Spectrom. 1997, 11, 769-773;
16. f) R. Bakhtiar, A. E. Kaifer, Rapid Commun. Mass Spectrom. 1998, 12, 111-114;
17. g) C. A. Shalley, R. K. Castellano, M. S. Brody, D. M. Rudkevich, G. Siuzdak, J. Rebek, Jr., J. Am. Chem. Soc. 1999, 121, 4568-4579.
18. a) E. M. Nuwaysir, J. A. Castoro, C. L.-C. Yang, C. L. Wilkins, J. Am. Chem. Soc. 1992, 114, 5748-5751;
19. b) B. J. Goolsby, J. S. Brodbelt, E. Adou, M. Blanda, Int. J. Mass Spectrom. 1999, 193, 197-204.
20. a) K. Laali, R. P. Lattimer, J. Org. Chem. 1989, 54, 496-498;
21. b) S. Kurono, T. Hirano, K. Tsu-Jimoto, M. Ohashi, M. Yoneda, Y. Ohkawa, Org. Mass Spectrom. 1992, 27, 1157-1160;
22. c) M. Sawada, M. Shizuma, Y. Takai, H. Yamada, T. Kaneda, T. Hanafusa, J. Am. Chem. Soc. 1992, 114, 4405-4406;
23. d) G. J. Langley, J. D. Kilburn, S. S. Flack, Org. Mass Spectrom. 1993, 28, 478-480;
24. e) S. Maleknia, J. S. Brodbelt, J. Am. Chem. Soc. 1993, 115, 2837-2843;
25. f) M. Sawada, Y. Okumura, M. Shizuma, Y, Takai, Y. Hidaka, H. Yamada, T. Tanaka, T. Kaneda, K. Hirose, S. Misumi, S. Takahashi, J. Am. Chem. Soc. 1993, 115, 7381-7388;
26. g) A. Mele, W. Panzeri, A. Selva, Eur. Mass Spectrom. 1997, 3, 347-354;
27. h) K. B. Reiche, I. Starke, E. Kleinpeter, H.-J. Holdt, Rapid Commun. Mass Spectrom. 1998, 12, 1021-1027;
28. i) M. Sawada, H. Yamaoka, Y. Takai, Y. Kawai, H. Yamada, T. Azuma, T. Fujioka, T. Tanaka, Int. J. Mass Spectrom. 1999, 193, 123-130.
29. a) M. Meot-Ner, J. Am. Chem. Soc. 1983, 105, 4906-4911;
30. b) A. K. Bose, O. Prakash, G. Y. Hu, J. Edasery, J. Org. Chem. 1983, 48, 1782-1784;
31. c) R. B. Sharma, A. T. Blades, P. Kebarle, J. Am. Chem. Soc. 1984, 106, 510-516;
32. d) C.-C. Liou, J. S. Brodhelt, J. Am. Chem. Soc. 1992, 114, 6761 -6764;
33. c) H. -F. Wu, J. S. Brodbelt, J. Am. Soc. Mass Spectrom. 1993, 4, 718-722.
34. a) H. -F. Wu, J. S. Brodbelt, J. Am. Chem. Soc. 1994, 116, 6418-6426;
35. b) E. J. Alvarez, V. H. Vartanian, J. S. Brodbelt, J. Am. Soc. Mass Spectrom. 1997, 8, 620-629;
36. c) S. M. Blair, E. C. Kempen, J. S. Brodbelt, J. Am. Soc. Mass Spectrom. 1998, 9, 1049-1059;
37. d) S. M. Blair, J. S. Brodbelt, G. M. Reddy, A. P. Marchand, J. Mass Spectrom. 1998, 33, 721-728;
38. a) H. Zhang, I.-H. Chu, S. Leming, D. V. Dearden, J. Am. Chem. Soc. 1991, 113, 7415-7417;
39. b) I.-H. Chu, H. Zhang, D. V. Dearden, J. Am. Chem. Soc. 1993, 115, 5736-5744;
40. c) I.-H. Chu, D. V. Dearden, J. Am. Chem. Soc. 1995, 117, 8197-8203;
41. d) Q. Chen, K. Cannell, J. Niccoll, D. V. Dearden, J. Am. Chem. Soc. 1996, 118, 6335-6341;
42. e) P. S. H. Wong, H.-J. Yu, D. V. Dearden, Inorg. Chim. Acta 1996, 246, 259-265;
43. f) D. V. Dearden, C. Dejsupa, Y. Liang, J. S. Bradshow, R. M. Izatt, J. Am. Chem. Soc. 1997, 119, 353-359;
44. g) K. A. Kellersberg, C. Dejsupa, Y.-Y. Liang, R. M. Pope, D. V. Dearden, Int. J. Mass Spectrom. 1999, 193, 181-195.
45. a) M. Vincenti, E. Dalcanale, P. Soncini, G. Guglielmetti, J. Am. Chem. Soc. 1990, 112, 445-447;
46. b) M. Vincenti, E. Pelizzetti, E. Dalcanale, P. Soncini, Pure Appl. Chem. 1993, 65, 1507-1512;
47. c) M. Vincenti, E. Pelizzetti, E. Dalcanale, P. Soncini, Pure Appl. Chem. 1995, 67, 1075-1084;
48. d) A. Arduini, M. Cantoni, E. Graviani, A. Pochini, A. Secchi, A. R. Sicuri, R. Ungaro, M. Vincenti, Tetrahedron 1995, 51, 599-606;
49. e) M. Vincenti, E. Dalcanale, J. Chem. Soc. Perkin Trans. 2 1995, 1969-1976.
50. a) T. Lippman, H. Wilde, E. Dalcanale, L. Mavilla, G. Mann, U. Heier, S. Spera, J. Org. Chem. 1995, 60, 235-242;
51. b) P. Delangle, J.-P. Dutasta, Tetrahedron Lett. 1995, 36, 9325-9328.
52. For a review on in - out isomerism see: R. W. Alder, S. P. East, Chem. Rev. 1996, 96, 2097-2111.
53. J. M. J. Nuutinen, A. Irico, M. Vincenti, E. Dalcanale, J. M. H. Pakarinen, P. Vainiotalo, J. Am. Chem. Soc. 2000, 122, 10090-10100.
54. T. Lippmann, E. Dalcanale, G. Mann, Tetrahedron Lett. 1994, 35, 1685-1688.
55. a) J. Pierce, K. L. Busch, R. A. Walton, R. G. Cooks, J. Am. Chem. Soc. 1981, 103, 2583-2588;
56. b) K. L. Busch, S. E. Unger, A. Vincze, R. G. Cooks, T. Keough, J. Am. Chem. Soc. 1982, 104, 1507-1511;
57. c) R. A. W. Johnstone, I. A. S. Lewis, M. E. Rose, Tetrahedron 1983, 39, 1587-1603;
58. d) G. Bonas, C. Sosso, M. R. Vignon, J. Indus. Phenom. Mol. Recog. Chem. 1989, 7, 637-647;
59. e) J. M. Miller, K. Balasanmugam, A. Fulcher, Org. Mass Spectrom. 1989, 24, 497-503;
60. f) T. Takahashi, A. Uchiyama, K. Yamada, B. C. Lynn, G. W. Gokel, Tetrahedron Lett. 1992, 33, 3825-3828;
61. g) J. B. Cunniff, P. Vouros, D. L. Kaplan, S. A. Fossey, J. Am. Soc. Mass Spectrom. 1994, 5, 638-648.
62. a) F. Inouchi, K. Araki, S. Shinkai, Chem. Lett. 1994, 1383-1386;
63. b) F. Inouchi, Y. Mihara, T. Inazu, S. Shinkai, Angew. Chem. 1995, 107, 1459-1462; Angew. Chem. Int. Ed. Engl. 1995, 34, 1364-1366.
64. b) F. Inouchi, Y. Mihara, T. Inazu, S. Shinkai, Angew. Chem. 1995, 107, 1459-1462; Angew. Chem. Int. Ed. Engl. 1995, 34, 1364-1366.
65. E. Dalcanale, P. Jacopozzi, F. Ugozzoli, G. Mann, Supramol. Chem. 1998, 9, 305-316.
66. Handbook of Chemistry and Physics, 73rd ed. (Ed. D. L. Lide), CRC, Boca Raton, 1992, Chapter 9, p. 53.
67. K. D. Cook, P. J. Todd, D. H. Friar, Biomed. Environ. Mass Spectrom. 1989, 18, 492-497.
68. a) R. G. Cooks, T. L. Kruger, J. Am. Chem. Soc. 1977, 99, 1279-1281;
69. b) S. A. McLuckey, D. Cameron, R. G. Cooks, J. Am. Chem. Soc. 1981, 103, 1313-1317.
70. E. P. Hunter, S. G. Lias, J. Phys. Chem. Ref. Data 1998, 27, 413.
71. a) E. Dalcanale, J. Hartmann, Sens. Actuators B 1995, 24-25;
72. b) E. Dalcanale, J. Hartmann, Sens. Actuators B 1995, 39-42.
73. R. Pinalli, F. F. Nachtigall, F. Ugozzoli, E. Dalcanale, Angew: Chem. 1999, 111, 2530-2533; Angew. Chem. Int. Ed. 1999, 38, 2377-2380.
74. R. Pinalli, F. F. Nachtigall, F. Ugozzoli, E. Dalcanale, Angew: Chem. 1999, 111, 2530-2533; Angew. Chem. Int. Ed. 1999, 38, 2377-2380.