Barrier to C-N rotation in selenoformamide: An ab initio study

Chemical Physics Letters

Volumn 276, Issue 1-2, 1997, Pages 31-38

  Prasad, Bharatam V ^a   Uppal, Punam ^a   Bassi, Parmjit S ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031565699     PISSN: 00092614     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0009-2614(97)88031-1     Document Type: Article

References (30)

1. Lehninger A.L., Nelson D.L., Cox M.M. Principles of Biochemistry. 1993;Worth, New York.
2. However, recent theoretical NMR (GIAO-MP2) study suggests the amide group probably is non-planar in peptides Sulzback H.M., Schleyer P.v.R., Schaefer H.F. J. Am. Chem. Soc. 117:1995;2632.
3. Pauling L. The Nature of the Chemical Bond. 1960;Cornell University Press, Ithaca, NY.
4. Wheland G.W. Resonance in Organic Chemistry. 1955;Wiley, New York.
5. Wiberg K.B., Laidig K.E. J. Am. Chem. Soc. 109:1987;5935.
6. Wiberg K.B., Breneman C.M. J. Am. Chem. Soc. 114:1992;831.
7. Wiberg K.B., Hadad C.M., Rablen P.R., Cioslowski J. J. Am. Chem. Soc. 114:1992;8644.
8. Laidig K.E., Cameron L.M. Can. J. Chem. 71:1993;872.
9. Wiberg K.B., Rablen P.R. J. Am. Chem. Soc. 117:1995;2201.
10. Ou M.-C., Tsai M.-S., Chu S.-Y. J. Mol. Struct. 310:1994;247.
11. March J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 1992;Wiley, New York.
12. Sandstrom J. J. Phys. Chem. 71:1967;2318.
13. Neuman R.C. Jr., Young L.B. J. Phys. Chem. 69:1965;2570.
14. Loewenstein A., Melera A., Rigny P., Walter W. J. Phys. Chem. 68:1964;1597.
15. Stewart W.E., Siddall T.H. III. Chem. Rev. 70:1979;517.
16. Laidig K.E., Cameron L.M. J. Am. Chem. Soc. 118:1996;1737.
17. Hehre W.J., Radom L., Schleyer P.v.R., Pople J.A. Ab Initio Molecular Orbital Theory. 1986;Wiley-Interscience, New York.
18. Frisch M.J., Trucks G.W., Schlegel H.B., Gill P.M.W., Johnson B.G., Robb M.A., Cheeseman J.R., Keith T., Petersson J.A., Montgomery J.A., Raghavachari K., Al-Laham M.A., Zakrzewski V.G., Ortiz J.V., Foresman J.B., Peng C.Y., Ayala P.Y., Chen W., Wong M.W., Andres J.L., Replogle E.S., Gomperts R., Martin R.L., Fox D.J., Binkley J.S., Defrees D.J., Baker J., Stewart J.P., Head-Gordon M., Gonzalez C., Pople J.A. Gaussian 94, Revision B.2. 1995;Gaussian, Inc. Pittsburgh, PA.
19. Lammertsma K., Prasad B.V. J. Am. Chem. Soc. 116:1994;642.
20. Pople J.A., Head-Gordon M., Fox D.J., Raghavachari K., Curtiss L.A. J. Chem. Phys. 90:1989;5622.
21. Reed A.E., Weinstock R.B., Weinhold F. J. Chem. Phys. 83:1985;735.
22. Reed A.E., Curtiss L.A., Weinhold F. Chem. Rev. 88:1988;899.
23. Leszczynski J., Kwiatkowski J.S., Leszczynska D. J. Am. Chem. Soc. 114:1992;10089. also refer to the following for corrections.
24. Leszczynski J., Kwiatkowski J.S., Leszczynska D. J. Am. Chem. Soc. 115:1993;5891.
25. Dapprich S., Frenking G. Chem. Phys. Lett. 205:1993;337.
26. Ruan M.-D., Zhang P.-F., Tao Y., Fan W.-Q. Synth. Commun. 26:1996;2617.
27. Segi M., Takahashi T., Ichinose I.H., Li G.M., Nakajima T. Tetrahedron Lett. 33:1992;7865.
28. 2=NH is 1.282 Å at MP2(FC)/6-31G* level.
29. At MP2(FC)/6-31G* level, the formamide shows pyramidal arrangement [one - ve frequency in the frequency (MP2) calculations], the planar structure being only 0.01 kcal/mol less stable. However, the inclusion of ZPE makes the planar structure more stable by the same amount. Hence, for all practical purposes, formamide can be considered as a planar molecule.
30. Lee J.D. 4th ed. Concise Inorganic Chemistry. 1991;Chapman & Hall, London.