Pathways of the reaction of nucleophilic addition of ammonia to formaldehyde in the gas phase and in the complex with formic acid: Ab initio calculations

Russian Chemical Bulletin

Volumn 47, Issue 1, 1998, Pages 8-16

  Minyaev, R M ^a  

^a SOUTHERN FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

Ammonia, formaldehyde, formic acid, nucleophilic addition; Reaction pathway, ab initio calculations

Indexed keywords

EID: 0032389103     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02495502     Document Type: Article

References (32)

1. W. P. Jencks, Catalysis in Chemistry and Biochemistry, McGraw-Hill, New York, 1969.
2. A. J. Kirby, Angew. Chem., Int. Ed. Engl., 1996, 35, 707; Adv. Phys. Org. Chem., 1994, 29, 87.
3. A. J. Kirby, Angew. Chem., Int. Ed. Engl., 1996, 35, 707; Adv. Phys. Org. Chem., 1994, 29, 87.
4. V. I. Minkin, B. Ya. Simkin, and R. M. Minyaev, Quantum Chemistry of Organic Compounds. Mechanisms of Reactions, Springer-Verlag, Berlin, 1990, 270 pp.
5. H. B. Burgi, J. D. Dunitz, J. M. Lehn, and G. Wipff, Tetrahedron, 1974, 30, 1563.
6. H. B. Burgi and J. D. Dunitz, Acc. Chem. Res., 1983, 16, 153.
7. Y.-T. Chang and G. H. Loew, J. Am. Chem. Soc., 1994, 116, 3548.
8. L. Pardo, R. Osman, H. Weinstein, and J. R. Rabinowitz, J. Am. Chem. Soc., 1993, 115, 8263.
9. J. L. Wilbur and J. I. Brauman, J. Am. Chem. Soc., 1994, 116, 5839.
10. O. N. Ventura, E. L. Coitino, A. Lledos, and J. Bertran, J. Comput. Chem., 1992, 13, 1037.
11. R. M. Minyaev, Usp. Khim., 1994, 63, 939 [Russ. Chem. Rev., 1994, 63, 883 (Engl. Transl.)].
12. R. M. Minyaev, Usp. Khim., 1994, 63, 939 [Russ. Chem. Rev., 1994, 63, 883 (Engl. Transl.)].
13. S. Scheiner, W. N. Lipscomb, and D. A. Kleier, J. Am. Chem. Soc., 1976, 98, 4770.
14. H. Yamataka, S. Nagase, T. Ando, and T. Nanafusa, J. Am. Chem. Soc., 1986, 108, 601.
15. I. H. Williams, J. Am. Chem. Soc., 1987, 109, 6299.
16. C. Kozmutza, E. M. Evleth, and E. Kapuy, J. Mol. Struct. (Theochem.), 1991, 233, 139.
17. J. B. Foresman and E. Frisch, Exploring Chemistry with Electronic Structure Methods, 2nd Ed., Gaussian, Inc., Pittsburgh (PA), 1996, 302 pp.
18. M. J. Frish, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. A. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, Gaussian-94, Revision B. 3, Gaussian, Inc., Pittsburgh (PA), 1995.
19. M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. J. Su, T. L. Windus, M. Dupuis, and J. A. Montgomery, J. Comput. Chem., 1993, 14, 1347.
20. R. Cammi, R. Bonaccorsi, and J. Tomasi, Theor. Chim. Acta, 1985, 68, 271.
21. F. F. Muguet and G. W. Robinson, J. Chem. Phys., 1995, 102, 3643 (see also references cited therein).
22. PCMODEL, Selena Software, Bloomigton (IN), 1987.
23. R. M. Minyaev and E. A. Lepin, Mendeleev Commun., 1997, 80.
24. P. Helminger and W. Gordy, Phys. Rev., 1969, 188, 100.
25. Y. Yamada, T. Nakagawa, K. Kuchisu, and Y. Morino, J. Mol. Spectrosc., 1971, 38, 70.
26. J. L. Derissen, J. Mol. Struct., 1971, 7, 67.
27. O. A. Osipov, V. I. Minkin, and A. D. Garnovskii, Spravochnik po dipol'nym momentam [Handbook of Dipole Moments], Vysshaya Shkola. Moscow. 1971, 414 pp. (in Russian).
28. K. S. Krasnov, N. V. Filippenko, V. A. Bobkova, N. L. Lebedeva, E. V. Morozov, T. I. Ustinova, and G. A. Romanova, Molekulyarnye postoyannye neorganicheskikh soedinenii [Molecular Constants of Inorganic Compounds], Khimiya, Leningrad, 1979, 446 pp. (in Russian).
29. G. A. Jeffrey and W. Saenger, Hydrogen Bonding in Biological Structures, Springer-Verlag, New York, 1991, 569 pp.
30. S. Scheiner, Acc. Chem. Res., 1994, 27, 402.
31. F. Hibbert, Adv. Phys. Org. Chem., 1986, 22, 113.
32. M. C. Etter, J. Phys. Chem., 1991, 95, 4601.