期刊
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
卷 23, 期 12, 页码 1155-1172出版社
WILEY
DOI: 10.1002/poc.1686
关键词
chiral discrimination; co-operativity; diketopiperazines; hydrogen bond; NEDA analysis
资金
- Ministerio de Ciencia e Innovacion [CTQ2009-13129-C02-02]
- Comunidad Autonoma de Madrid [S-0505/PPQ/0225]
The chiral discrimination in the self-association of 2,5-diketopiperazines derivatives has been studied using density functional theory (DFT) methods. Hence, clusters from dimers to tetramers have been considered. We have found a variety of linear and cyclic structures depending on the geometry of the monomers. In general, the heterochiral dimers (RR:SS or SS:RR) are more stable than the homochiral ones (RR:RR or 55:55) with slight energetic differences. Nevertheless, most of the larger clusters (trimers and tetramers) show changes in stability, the homochiral cyclic structures being favored due to the better geometry of the hydrogen bond and/or the higher number of interactions. Some interesting correlations between the hydrogen bond geometrical descriptors and theoretical parameters obtained from the Natural Bond Orbital analysis (NBO), Natural energy decomposition analysis (NEDA), and the Atoms in Molecules theory (AIM) have been found. The chiral discrimination in the recognition process of these self-complexes has been evaluated. In addition, evidence of cooperative effects has been observed. Copyright (C) 2010 John Wiley & Sons, Ltd.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据