A computational study of the isomerization of prolyl amides as catalyzed by intramolecular hydrogen bonding

Journal of Physical Chemistry A

Volumn 106, Issue 46, 2002, Pages 11168-11172

  Rankin, Kathryn N ^a   Boyd, Russell J ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

INTRAMOLECULAR HYDROGEN BONDING;

AROMATIC COMPOUNDS; CATALYSIS; HYDROGEN BONDS; PROBABILITY DENSITY FUNCTION;

ISOMERIZATION;

EID: 0037153247     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp020846k     Document Type: Article

References (27)

1. MacArthur, M.W.; Thornton, J.M. J. Mol. Biol. 1991, 218, 397.
2. Schmidt, F.X.; Mayr, L.M.; Mucke, M.; Schonbrunner, E.R. Adv. Protein Chem. 1993, 44, 25.
3. Eberhardt, E.S.; Loh, S.N.; Hinck, A.P.; Raines, R.T. J. Am. Chem. Soc. 1992, 114, 5437.
4. Stein, R.L. Adv. Protein Chem. 1993, 44, 1.
5. Pliyev, B.K.; Gurvits, B.Ya. Biochemistry 1999, 64, 738.
6. Fischer, S.; Dunbrack, R.L., Jr.; Karplus, M. J. Am. Chem. Soc. 1994, 116, 11931.
7. Fischer, S.; Michnick, S.; Karplus, M. Biochemistry 1993, 32, 13830.
8. Cox, C.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 10660.
9. Rankin, K.N.; Gauld, J.W.; Boyd, R.J. J. Am. Chem. Soc. 2000, 122, 5384.
10. Rankin, K.N.; Gauld, J.W.; Boyd, R.J. J. Am. Chem. Soc. 2001, 123, 2047.
11. Eberhardt, E.S.; Panasik, N., Jr.; Raines, R.T. J. Am. Chem. Soc. 1996, 118, 12261.
12. Cox, C.; Young, V.G., Jr.; Lectka, T. J. Am. Chem. Soc. 1997, 119, 2307.
13. Beausoleil, E.; Sharma, R.; Michnick, S.W.; Lubell, W.D. J. Org. Chem. 1998, 63, 6572 (and references cited within).
14. Beausoleil, E.; Lubell, W.D. J. Am. Chem. Soc. 1996, 118, 12902.
15. Jhon, J.S.; Kang, Y.K. J. Phys. Chem. A 1999, 103, 5436.
16. Kang, Y.K. J. Mol. Struct. (THEOCHEM) 2002, 585, 209.
17. Kang, Y.K. J. Phys. Chem. B 2002, 106, 2074.
18. Rablen, P.R. J. Org. Chem. 2000, 65, 7930.
19. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Zakrzewski, V.G.; Montgomery, J.A.; Stratmann, R.E.; Burant, J.C.; Dapprich, S.; Millam, J.M.; Daniels, A.D.; Kudin, K.N.; Strain, M.C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G.A.; Ayala, P.Y.; Cui, Q.; Morokuma, K.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Cioslowski, J.; Ortiz, J.V.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P.M.W.; Johnson, B.G.; Chen, W.; Wong, M.W.; Andres, J.L.; Head-Gordon, M.; Replogle, E.S.; Pople, J.A. GAUSSIAN 98, Gaussian, Inc.: Pittsburgh, PA, 1998.
20. Becke, A.D. J. Chem. Phys. 1993, 98, 1372.
21. Becke, A.D. J. Chem. Phys. 1993, 98, 5648.
22. Stephens, P.J.; Devlin, F.J.; Chabalowski, C.F.; Frisch, M.J. J. Phys. Chem. 1994, 98, 11623.
23. Lee, C.; Yang, W.; Parr, R.G. Phys. Rev. B 1987, 37, 785.
24. Madison, V. Biopolymers 1977, 16, 2671.
25. DeTar, D.F.; Luthra, N.P. J. Am. Chem. Soc. 1977, 99, 1232.
26. Kang, Y.K. J. Phys. Chem. 1996, 100, 11589.
27. Benzi, C.; Improta, R.; Scalmani, G.; Barone, V. J. Comput. Chem. 2002, 23, 341.