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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
Anizelli, Pedro R. [1] ; Vilcachagua, Janaina D. [1] ; Cunha Neto, Alvaro [1] ; Tormena, Claudio F. [1]
Total Authors: 4
Affiliation:
[1] Univ Estadual Campinas, Inst Chem, Dept Organ Chem, BR-13084971 Campinas, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: Journal of Physical Chemistry A; v. 112, n. 37, p. 8785-8789, SEP 18 2008.
Web of Science Citations: 13
Abstract

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)

FAPESP's process: 05/59649-0 - Conformational equilibria studies by nuclear magnetic resonance spectroscopy, infrared spectroscopy and theoretical calculations
Grantee:Roberto Rittner Neto
Support Opportunities: Research Projects - Thematic Grants