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Abstract:

Ab initio optimized geometries for three different methyl conformations of 2-methylpyridine were analyzed in order to study the nitrogen lone-pair proximity effect on a methyl C-H bond. Calculations were carried out using three different basis sets in order to determine how far the description ofthat effect depends on the wave function quality. They are 4-31G, 4-31G** and 6-31G**. Results thus obtained are discussed in terms of the hyperconjugative and the N lone-pair proximity effects. For an all-cis conformation with respect to the N lone-pair, a shortening of the methyl C-H bond was found, together with a redistribution of the electronic density along that bond. © 1992.

Registro:

Documento: Artículo
Título:Ab initio study of the nitrogen lone-pair proximity effect on a methyl C-H bond in 2-methylpyridine
Autor:Tufró, M.F.; Contreras, R.H.; Facelli, J.C.
Filiación:Departamento de Fisica, Facultad de Ciencias Exactas y Naturales, Uniuersidad de Buenos Aires, Ciudad Uniuersitaria, Pab. 1 (1428) Buenos Aires Argentina, Argentina
Utah Supercomputing Institute, The University of Utah, 3330 Merrill Engineering Building, Salt Lake City, UT 84112, United States
Año:1992
Volumen:254
Número:C
Página de inicio:271
Página de fin:277
DOI: http://dx.doi.org/10.1016/0166-1280(92)80071-S
Título revista:Journal of Molecular Structure: THEOCHEM
Título revista abreviado:J. Mol. Struct. THEOCHEM
ISSN:01661280
CODEN:THEOD
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01661280_v254_nC_p271_Tufro

Referencias:

  • Gil, von Philipsborn, Effect of electron lone-pairs on nuclear spin-spin coupling constants (1989) Magnetic Resonance in Chemistry, 27, p. 409
  • Krivdin, Zinchenko, Shcherbakov, Kalabin, Contreras, Tufro, Ruiz de Azua, Giribet, (1989) J. Magn. Reson., 84, p. 1
  • Biekofsky, Pomilio, Contreras, (1990) J. Mol. Struct. (Theochem), 210, p. 211
  • Contreras, Giribet, Ruiz de Azua, Cavasotto, Aucar, Krivdin, (1990) J. Mol. Struct. (Theochem), 210, p. 175
  • Diz, Giribet, de Azua, Contreras, (1989) Int. J. Quantum Chem., 84, p. 1
  • M.J. Frisch, J.S. Binkley, H.B. Schlegel, K. Poghavachar, C.F. Melius, R.L. Martin, J.J.P. Stewart, F.W. Bobrowicz, C.M. Rohffing, L.R. Kahn, D.J. Defrees, R. Seager, R.A. White- side, D.J. Fox, E.M. Fleuder and J.A. Pople, Camegie-Mellon Quantum Chemistry Publish- ing Unit, Pittsburgh, PA, 1984; Lambert, Nienhuis, (1980) J. Am. Chem. Soc., 102, p. 6659
  • Pross, Radom, Riggs, (1980) J. Am. Chem. Soc., 102, p. 2253
  • Williams, van Alsenoy, Scarsdale, Schafer, (1981) J. Mol. Struct. (Theochem), 86, p. 103
  • Hoffman, Long range spin-spin interactions in high resolution nuclear magnetic resonance and the concept of hyperconjugation (1958) Molecular Physics, 1, p. 326
  • Kowalewski, (1977) Prog. Nucl. Magn. Reson. Spectrosc., p. 1
  • Kowalewski, Contreras, (1972) J. Magn. Reson., 8, p. 101
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Citas:

---------- APA ----------
Tufró, M.F., Contreras, R.H. & Facelli, J.C. (1992) . Ab initio study of the nitrogen lone-pair proximity effect on a methyl C-H bond in 2-methylpyridine. Journal of Molecular Structure: THEOCHEM, 254(C), 271-277.
http://dx.doi.org/10.1016/0166-1280(92)80071-S
---------- CHICAGO ----------
Tufró, M.F., Contreras, R.H., Facelli, J.C. "Ab initio study of the nitrogen lone-pair proximity effect on a methyl C-H bond in 2-methylpyridine" . Journal of Molecular Structure: THEOCHEM 254, no. C (1992) : 271-277.
http://dx.doi.org/10.1016/0166-1280(92)80071-S
---------- MLA ----------
Tufró, M.F., Contreras, R.H., Facelli, J.C. "Ab initio study of the nitrogen lone-pair proximity effect on a methyl C-H bond in 2-methylpyridine" . Journal of Molecular Structure: THEOCHEM, vol. 254, no. C, 1992, pp. 271-277.
http://dx.doi.org/10.1016/0166-1280(92)80071-S
---------- VANCOUVER ----------
Tufró, M.F., Contreras, R.H., Facelli, J.C. Ab initio study of the nitrogen lone-pair proximity effect on a methyl C-H bond in 2-methylpyridine. J. Mol. Struct. THEOCHEM. 1992;254(C):271-277.
http://dx.doi.org/10.1016/0166-1280(92)80071-S