Theoretical study of formamide tautomers - A discussion of enol-keto isomerizations and their corresponding energies

Structural Chemistry

Volumn 15, Issue 4, 2004, Pages 309-316

  Liu, Min Hsien ^a   Chen, Cheng ^a   Liu, Chuan Wen ^a  

^a NATIONAL DEFENSE UNIVERSITY   (Taiwan)

Author keywords

Internal rotation; Localized analysis; Proton transfer; Tautomers of formamide molecule; Trans effect

Indexed keywords

FORMAMIDE;

CHEMICAL BOND; DENSITY FUNCTIONAL THEORY; ELECTRON; ENERGY; ISOMERIZATION; MOLECULAR MODEL; MOLECULAR STABILITY; MOLECULE; PROTON TRANSPORT; REVIEW; ROTATION;

EID: 3843123497     PISSN: 10400400     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:STUC.0000026745.14260.cf     Document Type: Review

References (38)

1. Kwiatkowski, J. S.; Bartlett, R. D.; Person, W. B. J. Amer. Chem. Soc. 1988, 107, 2353.
2. Bredereck, H.; Gompper, R.; Effenberger, F.; Popp, K. H.; Simchen, G. Chem. Ber. 1961, 94, 1241.
3. Pauling, L.; Sherman, J. J. Chem. Phys. 1933, 1, 606.
4. Ladell, J.; Post, B. Acta Crystallogr. 1954, 7, 559.
5. Stevens, E. D.; Rys, J.; Coppens, P. J. Amer. Chem. Soc. 1978, 100, 2324.
6. Radom, L.; Hehre, W. J.; Pople, J. A. J. Amer. Chem. Soc. 1971, 93, 289.
7. Hashmall, J.; Raynor, A. S. J. Chem. Phys. 1973, 58, 5464.
8. Hughes, D. O. Tetrahedron 1968, 24, 6423.
9. Kurland, R. J.; Wilson, E. B. J. Chem. Phys. 1957, 27, 585.
10. Bak, B.; Hansen-Nygaard, L. J. Chem. Phys. 1960, 33, 418.
11. Mortensen, A.; Nielsen, O. F. Spectrochim. Acta A 1995, 51, 1345.
12. Murrell, J. N.; Zhu, Z. H. J. Mol. Struct. 1983, 103, 235.
13. Sugawara, Y.; Hamada, Y.; Tsuboi, M. Bull. Chem. Soc. Jpn. 1983, 56, 1045.
14. Headley, A. D.; Nam, J. J. Mol. Struct. (Theochem) 2002, 589, 423.
15. Ilieva, S.; Hadjieva, B.; Galabov, B. J. Mol. Struct. 1999, 476, 151.
16. Madappat, K. V.; Clark, M.; Thrasher, J. S. J. Mol. Struct. (Theochem) 1993, 285, 1.
17. Brown, R. D.; Godfrey, P. D.; Kleibomer, B. J. Mol. Spectrosc. 1987, 124, 34.
18. Perricaudet, M.; Pullman, A. Intern. J. Pept. Protein Res. 1973, 5, 99.
19. Laidig, K. E.; Cameron, L. M. Can. J. Chem. 1993, 71, 872.
20. Pople, J. A. J. Amer. Chem. Soc. 1975, 97, 5308.
21. Nalewajski, R. F. J. Amer. Chem. Soc. 1978, 100, 41.
22. Bour, P.; Bednarova, L. J. Phys. Chem. 1995, 9, 5961.
23. Marchese, F. T.; Mehrotra, P. K.; Beveridge, D. L. J. Phys. Chem. 1984, 88, 5692.
24. Rao, C. N. R.; Rao, K. G.; Goel, A.; Balasubramanian, D. J. Chem. Soc. A 1971, p. 3077.
25. Tomlinson, R. V.; Tener, G. M. J. Amer. Chem. Soc. 1962, 84, 2644.
26. Fouda, A. S.; Gouda, M. M. Indian J. Chem. A. 1980, 19, 896.
27. Chen, C.; Ellison, F. O.; Chang, M. J. Chou, J. Chin. Chem. Soc. 1985, 32, 385.
28. Chen, C.; Chang, C. W.; Wang, Y. M. J. Mol. Struct. (Theochem) 1994, 311, 19.
29. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
30. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
31. Frisch, M. J. et al. GAUSSIAN 94, Revision B.2; Gaussian, Inc.: Pittsburgh, PA. 1995; GAUSSIAN 94, Revision A. 7, Gaussian, Inc.: Pettsburgh, PA, 1998.
32. Frisch, M. J. et al. GAUSSIAN 94, Revision B.2; Gaussian, Inc.: Pittsburgh, PA. 1995; GAUSSIAN 94, Revision A. 7, Gaussian, Inc.: Pettsburgh, PA, 1998.
33. Ayala, P. Y; Schlegel, H. B. J. Chem. Phys. 1997, 107, 375.
34. James B. Foresman and Aeleen Frisch Exploring Chemistry with Electronic Structure Method, 2nd edn.; Gaussian, Inc.: Pittsburgh, PA, 1996, p. 64.
35. Atkin, Physical Chemistry; 5th edn., W. H. Freeman: San Francisco. Table 2.9; 1994; p. 7C.
36. Chen, C. J. Chin. Chem. Soc. (Taiwan) 1972, 19, 19.
37. Chen, C. J. Chin. Chem. Soc. (Taiwan) 1979, 26, 153.
38. Chen, C. J. Chin. Chem. Soc. (Taiwan) 1983, 30, 21.