Alkyl Group Effect on the Conformational Isomerism of trans-2-Bromoalkoxycyclohexanes Analyzed by NMR Spectroscopy and Theoretical Calculations

被引：8

作者：

Silla, Josue M. ^{[1
]}

Cormanich, Rodrigo A. ^{[2
]}

Duarte, Claudimar J. ^{[3
]}

Freitas, Matheus P. ^{[1
]}

Ramalho, Teodorico C. ^{[1
]}

Barbosa, Thais M. ^{[2
]}

Santos, Francisco P. ^{[2
]}

Tormena, Claudio F. ^{[2
]}

Rittner, Roberto ^{[2
]}

机构：

[1] Univ Fed Lavras, Dept Chem, BR-37200000 Lavras, MG, Brazil

[2] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP, Brazil

[3] Univ Fed Sao Carlos, Dept Chem, BR-13565905 Sao Carlos, SP, Brazil

来源：

JOURNAL OF PHYSICAL CHEMISTRY A | 2011年 / 115卷 / 35期

基金：

巴西圣保罗研究基金会;

关键词：

TRANS-2-HALOCYCLOHEXANOLS;

D O I：

10.1021/jp206136t

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Suitable (3)J(H,H) coupling constants and theoretical calculations were used to define the conformational preferences of trans-2-bromoalkoxycyclohexanes (alkoxy = OMe, OEt, (OPr)-Pr-i, and (OBu)-Bu-t) 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 CCl4 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.

引用

页码：10122 / 10127

页数：6

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