Stereoelectronic interaction and their effects on conformational preference for 2-substituted methylenecyclohexane: An experimental and theoretical investigation

Autor(es)

Anizelli, Pedro R. ^[1] ; Vilcachagua, Janaina D. ^[1] ; Cunha Neto, Alvaro ^[1] ; Tormena, Claudio F. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Inst Chem, Dept Organ Chem, BR-13084971 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Physical Chemistry A; v. 112, n. 37, p. 8785-8789, SEP 18 2008.
• Citações Web of Science: 13

Resumo

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). (AU)

• Processo FAPESP: 05/59649-0 - Estudos de estrutura eletrônica e molecular através de métodos espectroscópicos e cálculos teóricos
• Beneficiário: Roberto Rittner Neto
• Modalidade de apoio: Auxílio à Pesquisa - Temático
• Processo FAPESP: 06/03980-2 - Interacoes de orbitais e seus efeitos nas constantes de acoplamento escalar em rmn: estudo experimental e teorico.
• Beneficiário: Claudio Francisco Tormena
• Modalidade de apoio: Auxílio à Pesquisa - Regular