Flexibility, association constants, and salt effects in organic ion pairs: How single bonds affect molecular recognition

Chemistry - A European Journal

Volumn 5, Issue 4, 1999, Pages 1284-1290

  Hossain, M Alamgir ^a   Schneider, Hans Jörg ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Association energy; Conformation; Ion pairs; Molecular recognition; Salt effect

Indexed keywords

ANION; SODIUM CHLORIDE;

ACID BASE BALANCE; ANISOTROPY; ARTICLE; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; COVALENT BOND; DISSOCIATION CONSTANT; ION TRANSPORT; IONIC STRENGTH; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE;

EID: 0032892572     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990401)5:4<1284::AID-CHEM1284>3.0.CO;2-6     Document Type: Article

References (53)

1. F. Diederich, Cyclophanes (Monographs in Supramolecular Chemistry) (Ed.: J. F. Stoddart), Royal Society of Chemistry, Cambridge, 1991, Ch. 4, p. 140 ff.
2. B. Hamelin, L. Jullien, F. Guillo, J. M. Lehn, A. Jardy, J. Phys. Chem. 1995, 99, 17877.
3. a) V. Krai, H. Furuta, K. Shreder, V. Lynch, J. L. Sessler, J. Am. Chem. Soc. 1996, 118, 1595;
4. b) M. I. Nelen. A. V. Eliseev, J. Chem. Soc. Perkin Trans. 2, 1997, 7, 1359;
5. c) Y. Kato, M. M. Conn, J. Rebek, J. Am. Chem. Soc. 1994, 116, 3279.
6. For recent references see a) C. De Stefano, C. Foti, O. Giufre, S. Sammartano, Talanta, 1996, 43, 707;
7. b) P. G. Daniele, E. Prenesti, A. Derobertis, C. De Stefano, Ann. Chim. (Rome) 1997, 87, 415;
8. c) P. G. Daniele, E. Prenesti, C. De Stefano, S. Sammartano, Journal of Solution Chemistry, 1995, 24, 325.
9. For leading references see a) K. Mernissiarifi, M. Zenkouar, G. Schlewer, B. Spiess, J. Chem. Soc. Faraday Trans. 1996, 92, 3101;
10. b) D. Esposito, P. Delvecchio, G. Barone, J. Am. Chem. Soc. 1997, 11, 2606.
11. For leading references see a) K. A. Sharp, A. Kim, B. Honig, Curr. Opin. Struct. Biol. 1995, 5, 323;
12. b) V. Buckin, H. Tran, V. Morozov, L. A. Marky, J. Am. Chem. Soc. 1996, 118, 7033.
13. G. E. Marlow, J. S. Perkyns, B. M. Pettitt, Chem. Rev. 1993, 93, 2503.
14. S. Tomac, M. Sarkar, T. Ratilainen, P. Wittung, J. Am. Chem. Soc. 1996, 118, 5544.
15. See, for example, J. M. Gao, M. Mammen, G. M. Whitesides, Science 1996, 272, 535.
16. For recent literature see a) M. C. Gennaro, S. Angelino, J. Chromatogr. A 1997, 789, 181;
17. b) P. Janos, J. Chromatogr. A 1995, 699, 1;
18. c) M. C. Gennaro, Adv. Chromatogr. (N.Y.) 1995, 35, 343;
19. d) E. M. Basova, T. A. Bol'shova, V. M. Ivanov, J. Anal. Chem. USSR Engl. Transl. 1996, 51, 638.
20. a) J. O'M, Bockris, A. K. N. Reddy, Modern Electrochemistry, Plenum, New York, 1970;
21. b) J. E. Gordon, The Organic Chemistry of Electrolyte Solutions, Wiley, New York, 1975;
22. c) A. Marcus, Ion Salvation, Wiley, Chichester, 1986;
23. d) K. Burger, Solvation, Ionic and Complex Formation Reactions in Non-Aqueous Solvents, Elsevier, Amsterdam, 1983;
24. e) Ions and Ion Pairs in Organic Reactions (Ed.: M. Szwarc), Wiley, New York, 1972;
25. f) B. E. Conway in Comprehensive Treatise on Electrochemistry, Vol. 5 (Eds.: B. E. Conway, J. O'M, Bockris, E. Yeager), Plenum, New York, 1983, p. 111;
26. g) Polyelectrolytes: Science and Technology (Ed.: M. Hara), M. Dekker, New York, Basel, 1993.
27. For recent references see a) T. Liljefors, P. O. Norrby, J. Am. Chem. Soc. 1997, 119, 1052;
28. b) A. P. Lyubartsev, L. Nordenskiold, J. Phys. Chem. B. 1997, 101, 4335;
29. c) J. L. Hecht, B. Honig, Y. K. Shin, W. L. Hubbell, J. Phys. Chem. 1995, 99, 7782;
30. d) T. Asada, K. Nishimoto, Mol. Simul. 1996, 16,307;
31. e) A. D. J. Haymet, J. Mol. Liq. 1995, 65/66, 139.
32. G. S. Manning, Rev. Biophys. 1975, 14, 2137; for a recent discussion of the Poisson - Boltzmann model see J. P. Bond, C. F. Anderson, M. T. Record, Biophys. J. 1994, 67, 825.
33. G. S. Manning, Rev. Biophys. 1975, 14, 2137; for a recent discussion of the Poisson - Boltzmann model see J. P. Bond, C. F. Anderson, M. T. Record, Biophys. J. 1994, 67, 825.
34. a) H.-J. Schneider, T. Schiestel, P. Zimmermann, J. Am. Chem. Soc. 1992, 114, 7698;
35. b) H.-J. Schneider, T. Blatter, A. Eliseev, V. Rüdiger, O. A. Raevsky, Pure Appl. Chem. 1993, 65, 2329;
36. c) H.-J. Schneider, Chem. Soc. Rev. 1994, 22, 227;
37. d) H.-J. Schneider, I. Theis, Angew. Chem. 1989, 101, 757; Angew. Chem. Int. Ed. Engl. 1989, 28, 753;
38. d) H.-J. Schneider, I. Theis, Angew. Chem. 1989, 101, 757; Angew. Chem. Int. Ed. Engl. 1989, 28, 753;
39. e) for related use of group contributions see N. Cohen, S. W. Benson, Chem. Rev. 1993, 93, 2419.
40. a) H.-J. Schneider, R. Kramer, S. Simova, U. Schneider, J. Am. Chem. Soc. 1988, 110, 6442;
41. b) H.-J. Schneider, I. Theis, J. Org. Chem. 1992, 57, 3066.
42. See S.-C. Tarn, R. J. P. Williams, Struct. Bonding (Berlin), 1985, 63, 103.
43. a) D. H. Williams, M. S. Searle, M. S. Westwell, V. Mackay, P. Groves, D. A. Beauregard, Chemtracts Org. Chem. 1994, 7, 133;
44. b) M. S. Searle, D. H. Williams, U. Gerhard, J. Am. Chem. Soc. 1992, 114, 10697, and references therein;
45. c) P. Groves, M. S. Searle, M. S. Westwell, D. H. Williams, J. Chem. Soc. Chem. Commun. 1994, 1519.
46. a) B. R. Brooks, R. E. Bruccoleri, B. D. Olafson, D. J. States, S. Swaminathan, M. Karplus, J. Comp. Chem. 1983, 4, 187;
47. b) C. L. Brooks, M. Karplus, Methods Enzymol. 1986, 127, 369;
48. c) A. T. Brünger, M. Karplus, Acc.Chem.Res. 1991, 24, 54.
49. F. Ehlinger, H.-J. Schneider, Angew. Chem. 1998, 110, 821; Angew. Chem. Int. Ed. 1998, 37, 826.
50. F. Ehlinger, H.-J. Schneider, Angew. Chem. 1998, 110, 821; Angew. Chem. Int. Ed. 1998, 37, 826.
51. Y. Marcus, Chem. Soc. Rev. 1993, 21, 409.
52. See R. Lumry in Bioenergetics and Thermodynamics (Ed.: A. Braibanti), Reidel, Dordrecht, 1980, p. 405, and references therein.
53. Dichloro derivatives of quaternary ammonium ions were obtained with a method similar to that described for the preparation of 1.4-di(trimethylammonium)tetramethylene diiodide; see R. M. Fuoss, V. F. H. Chu, J. Am. Chem. Soc. 1951, 73, 949.