Artículos de revistas
Stereoelectronic interaction and their effects on conformational preference for 2-substituted methylenecyclohexane: An experimental and theoretical investigation
Registro en:
Journal Of Physical Chemistry A. Amer Chemical Soc, v. 112, n. 37, n. 8785, n. 8789, 2008.
1089-5639
WOS:000259140400039
10.1021/jp8048636
Autor
Anizelli, PR
Vilcachagua, JD
Cunha, A
Tormena, CF
Institución
Resumen
Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) Conformational preferences for 2-substituted methylenecyclohexanes were determined using (3)JH(2)H(3) spin-spin coupling constants, while stereoelectronic interactions were obtained by means of theoretical calculations and NBO analysis. The conformational equilibrium of compounds studied can be represented by their axial and equatorial conformers, the axial conformers being the most stable form in polar and nonpolar solvents. These conformational preferences were attributed to the hyperconjugative interactions between the pi(C-C)->sigma*(C-Xax). and sigma(C-H)->sigma*(C-Xax) orbitals, and the repulsive steric interaction observed between sigma(C-H)-> n(Xeq). 112 37 8785 8789 Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) FAPESP [05/59649-0, 06/03980-2]