Vibrational circular dichroism spectroscopy of chiral pheromones: frontalin (1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane)

被引：45
作者：
Ashvar, CS
Stephens, PJ [1 ]
Eggimann, T
Wieser, H
机构：
[1] Univ So Calif, Dept Chem, Los Angeles, CA 90089 USA
[2] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada
来源：
TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 07期
基金：
美国国家卫生研究院;
关键词：
D O I：
10.1016/S0957-4166(98)00099-8
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Ab initio density functional theory (DFT) is used to predict the vibrational absorption and circular dichroism spectra of the insect pheromone 1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane: frontalin. Excellent agreement with experimental spectra is obtained for the structure in which the six-membered ring is in a chair conformation and the seven-membered ring is in a boat conformation. Vibrational circular dichroism (VCD) intensities, predicted on the basis of the previously determined absolute configuration, are in excellent agreement with experiment. We conclude that VCD spectroscopy, in combination with ab initio DFT, is now an efficient tool for determining the absolute configuration and/or conformation of chiral organic molecules, including pheromones. (C) 1998 Elsevier Science Ltd. All rights reserved.
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收藏
页码：1107 / 1110
页数：4
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