Alkyl group effect on the conformational isomerism of trans-2-bromoalkoxycyclohexanes analyzed by nmr spectroscopy and theoretical calculations.

Silla, Josué M; Cormanich, Rodrigo A; Duarte, Claudimar J; Freitas, Matheus P; Ramalho, Teodorico C; Barbosa, Thaís M; Santos, Francisco P; Tormena, Cláudio F; Rittner, Roberto

Silla, Josué M; Cormanich, Rodrigo A; Duarte, Claudimar J; Freitas, Matheus P; Ramalho, Teodorico C; Barbosa, Thaís M; Santos, Francisco P; Tormena, Cláudio F; Rittner, Roberto.

Afiliación

Silla JM; Department of Chemistry, Federal University of Lavras, CP 3037, 37200-000, Lavras, MG, Brazil.

J Phys Chem A ; 115(35): 10122-7, 2011 Sep 08.

Article en En | MEDLINE | ID: mdl-21793564

RESUMEN

Suitable (3)J(H,H) coupling constants and theoretical calculations were used to define the conformational preferences of trans-2-bromoalkoxycyclohexanes (alkoxy = OMe, OEt, O(i)Pr, and O(t)Bu) for the isolated molecule and as a function of the medium. The diaxial conformer was preponderant, or at least similarly populated to the diequatorial form, for the tert-butoxy derivative only, while the diequatorial conformer was prevalent for the remaining alkoxy derivatives (except for the OMe derivative in CCl(4) solution). The conformational behavior of these compounds was analyzed on the basis of classical steric effects and attractive electron delocalizations, by means of natural bond orbital analysis.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Phys Chem A Asunto de la revista: QUIMICA Año: 2011 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Estados Unidos

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