pKHB and enthalpic scales of the hydrogen bond acceptor of thioethers, thiols and disulfides;Échelles pKHB et enthalpique du pouvoir accepteur de liaison hydrogène de thioéthers, thiols et disulfures

Canadian Journal of Chemistry

Volumn 83, Issue 2, 2005, Pages 138-145

  Laurence, Christian ^a   Berthelot, Michel ^a   Evain, Karine ^a   Illien, Bertrand ^a  

^a UNIVERSITÉ DE NANTES   (France)

Author keywords

Disulfides; Hydrogen bond; pKHB scale; Thioethers; Thiols

Indexed keywords

COMPLEXATION; ENTHALPY; HYDROGEN BONDS; INFRARED SPECTROSCOPY; KETONES; PHENOLS; PHOSPHORUS COMPOUNDS; POLARIZATION;

4-FLUOROPHENOL; DISULFIDES; HYDROGEN BOND ACCEPTOR (HBA); IR SPECTROMETRY;

ETHERS;

4 FLUOROPHENOL; ACID; ALKYL GROUP; BASE; CARBON TETRACHLORIDE; CHLORINE; DISULFIDE; HYDROGEN; ISOTHIOCYANIC ACID; OXYGEN; PHENOL DERIVATIVE; PHOSPHINE; SULFIDE; SULFUR; THIOAMIDE; THIOKETONE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; COMPLEX FORMATION; CYCLIZATION; ENTHALPY; HYDROGEN BOND; INFRARED SPECTROMETRY; REACTION ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 19044394467     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v05-007     Document Type: Article

References (48)

1. C. Laurence et M. Berthelot. Perspect. Drug Discovery Des. 18, 39 (2000).
2. R.W. Taft, D. Gurka, L. Joris, P.v.R. Schleyer et J.W. Rakshys. J. Am. Chem. Soc. 91, 4801 (1969).
3. E.M. Arnett, L. Joris, E. Mitchell, T.S.S.R. Murty, T.M. Gorrie et P.v.R. Schleyer. J. Am. Chem. Soc. 92, 2365 (1970).
4. G.C. Pimentel et A.L. McClellan. The hydrogen bond. Freeman, San Francisco. 1960.
5. G.A. Jeffrey et W. Saenger. Hydrogen bonding in biological structures. Springer-Verlag, Berlin. 1991.
6. C. Laurence, M. Berthelot, J.-Y. Le Questel et M.J. El Ghomari. J. Chem. Soc. Perkin Trans. 2, 2075 (1995).
7. B. Illien, K. Evain, M. Berthelot et C. Laurence. J. Phys. Org. Chem. 16, 608 (2003).
8. O. Exner. Prog. Phys. Org. Chem. 10, 411 (1973).
9. R.M. Badger et S.H. Bauer. J. Chem. Phys. 5, 839 (1937).
10. R.M. Badger. J. Chem. Phys. 8, 288 (1940).
11. C. Laurence, M. Berthelot et J. Graton. Dans The chemistry of phenols. Vol. part 1. Sous la direction de Z. Rappoport. Wiley, New York. 2003.
12. J. Graton, F. Besseau, M. Berthelot, E.D. Raczynska et C. Laurence. Can. J. Chem. 80, 1375 (2002).
13. C. Ouvrard, M. Berthelot et C. Laurence. J. Phys. Org. Chem. 14, 804 (2001).
14. R. Foster. Organic charge-transfer complexes. Academic Press, Londres. 1969.
15. C. Ouvrard, M. Berthelot et C. Laurence. J. Chem. Soc. Perkin Trans. 2, 1357 (1999).
16. F. Besseau, C. Laurence et M. Berthelot. Bull. Soc. Chim. Fr. 133, 381 (1996).
17. M. Berthelot, F. Besseau et C. Laurence. Eur. J. Org. Chem. 925 (1998).
18. C. Ouvrard, M. Lucon, J. Graton, M. Berthelot et C. Laurence. J. Phys. Org. Chem. 17, 56 (2004).
19. R. West, D.L. Powell, L.S. Whatley, M.K.T. Lee et P.v.R. Schleyer. J. Am. Chem. Soc. 84, 3221 (1962).
20. R. West, D.L. Powell, M.K.T. Lee et L.S. Whatley. J. Am. Chem. Soc. 86, 3227 (1964).
21. R. West, L.S. Wilson et D.L. Powell. J. Organomet. Chem. 178, 5 (1979).
22. J. Chojnowski et W.W. Brandt. J. Am. Chem. Soc. 90, 1384 (1968).
23. V. Sara, J. Moravec, V. Horak et M. Horak. Collect. Czech. Chem. Commun. 34, 2390 (1969).
24. G.C. Vogel et R.S. Drago. J. Am. Chem. Soc. 92, 5347 (1970).
25. A.D. Sherry et K.F. Purcell. J. Am. Chem. Soc. 94, 1848 (1972).
26. J.L.M. Abboud, C. Roussel, E. Gentric, K. Sraidi, J. Lauransan, G. Guiheneuf, M.J. Kamlet et R.W. Taft. J. Org. Chem. 53, 1545 (1988).
27. E.M. Arnett, E.J. Mitchell et T.S.S.R. Murty. J. Am. Chem. Soc. 96, 3875 (1974).
28. F.H. Allen, C.M. Bird, R.S. Rowland et P.R. Raithby. Acta Crystallogr. B, B53, 680 (1997).
29. J.A. Platts, S.T. Howard et B.R.F. Bracke. J. Am. Chem. Soc. 118, 2726 (1996).
30. R.G. Pearson. J. Am. Chem. Soc. 85, 3533 (1963).
31. R.G. Parr et R.G. Pearson. J. Am. Chem. Soc. 105, 7512 (1983).
32. J.Y. Le Questel, C. Laurence, A. Lachkar, M. Helbert et M. Berthelot. J. Chem. Soc. Perkin Trans. 2, 2091 (1992).
33. A. Chardin. Thèse de doctorat, Université de Nantes, Nantes, France. 1997.
34. E.D. Becker. Spectrochim. Acta, 17, 436 (1961).
35. D.L. Powell et R. West. Spectrochim. Acta, 20, 983 (1964).
36. S. Singh, A.S.N. Murthy et C.N.R. Rao. Trans. Faraday Soc. 62, 1056 (1966).
37. T. Gramstad et J. Sandstrom. Spectrochim. Acta, Part A, 25, 31 (1969).
38. P. Goralski. J. Chem. Soc. Faraday Trans. 89, 2433 (1993).
39. J. Rossarie, J.P. Gallas, C. Binet et R. Romanet. J. Chim. Phys. Phys.-Chim. Biol. 75, 63 (1978).
40. M.H. Abraham, D.V. Prior, R.A. Schulz, J.J. Morris et P.J. Taylor. J. Chem. Soc. Faraday Trans. 94, 879 (1998).
41. V. Gutmann. Electrochim. Acta, 21, 661 (1976).
42. C. Ouvrard, M. Berthelot, T. Lamer et O. Exner. J. Chem. Inf. Comput. Sci. 41, 1141 (2001).
43. W.J. Hehre, C.F. Pau, A.D. Headley, R.W. Taft et R.D. Topsom. J. Am. Chem. Soc. 108, 1711 (1986).
44. C. Mansch, A. Leo et R.W. Taft. Chem. Rev. 91, 165 (1991).
45. M. Charton. Top. Curr. Chem. 114, 57 (1983).
46. A.E. Reed, R.B. Weinstock et F. Weinhold. J. Chem. Phys. 83, 735 (1985).
47. E.D. Glendening, A.E. Reed, J.E. Carpenter et F. Weinhold. Natural Bond Orbital (NBO). Version, 3,1.
48. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, J.T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Kiene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez et J.A. Pople. GAUSSIAN 03. Rev C,01 [programme d'ordinateur]. Wallingford, USA. 2004.