Electronic Interactions and Their Influence on the Conformational Stability of trans-2-Halocyclopentanol

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• 作者：Clá ; udio F. Tormena ; Francisco P. dos Santos ; Alvaro Cunha Neto ; Roberto Rittner ; Fabiana Yoshinaga ; Jacqueline C. T. Temistocles
• 刊名：Journal of Physical Chemistry A
• 出版年：2007
• 出版时间：January 18, 2007
• 年：2007
• 卷：111
• 期：2
• 页码：295 - 298
• 全文大小：41K
• 年卷期：v.111,no.2(January 18, 2007)
• ISSN：1520-5215

文摘

Conformational preferences and electronic interactions of trans-2-fluorocyclopentanol (1), trans-2-chlorocyclopentanol (2), and trans-2-bromocyclopentanol (3) were analyzed using experimental and theoretical ³J_HHcoupling constants, theoretical calculations, and natural bond orbital (NBO) analysis. The conformationalequilibria of compounds 1-3 can be represented by their diaxial and diequatorial conformers as supportedby theoretical calculations. From ³J_HH coupling constant values, it can be found that the diequatorial conformeris present in the equilibrium as 55% for compound 1 and as 60% for compounds 2 and 3. This behavior isin agreement with orbital interaction analyses obtained from NBO.