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首页> 外文期刊>Physical chemistry chemical physics: PCCP >Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group
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Does aromaticity account for an enhanced thermodynamic stability? The case of monosubstituted azaborines and the stereoelectronic chameleonism of the NH2 group

机译：芳香性是否有增强的热力学稳定性？ 单份氮杂杂志的情况和NH2组的立体电动变色件

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摘要

This work was initiated by the increasing interest in BN/CC isosterism and by the long-lasting interest in the concepts of aromaticity and substituent effects. We have theoretically examined the aromaticity and stability of monosubstituted BN isosters of benzene, the three isomeric azaborines. The results provide insight into the effect of substitution on two basic molecular properties, which are influenced, here, by the substituent effects and by the B/N relationship in the ring. The results, along with other examples in the literature, also warn chemists that the general belief that aromaticity accounts for enhanced thermodynamic stability is not always true. The stability of cyclic, conjugated compounds depends on several effects, and only one of them is aromaticity. In addition, our calculations predict a switching of electronic properties of the NH2 group from the usual p-electron donor to a pi-electron acceptor when it is moved from the B/C atoms to the nitrogen atom in all isomers, or C6 in 1,3-azaborine. This is the result of the conformational change that places the N-LP in the plane of the ring and the NH bonds in a favourable spatial position to act as acceptors of pi-electron density.
机译：这项工作是由在BN / CC电子等排了越来越多的关注，并通过在芳香和取代基效应的概念的持久兴趣开始。我们从理论上研究了芳香和苯的单取代BN等排的稳定性，这三个异构azaborines。结果提供了洞察取代对两个基本分子特性，其影响，在这里，通过该取代基的影响，并通过该环中的B / N的关系的影响。结果，与文献其它例子一起，也警告化学家，一般认为芳香占增强的热力学稳定性并非总是如此。环状，共轭系化合物的稳定性取决于几个方面的影响，并且只有它们中的一个是芳香性。此外，我们的计算预测从通常的p型电子给体与π电子受体的NH 2基团的电子特性的开关，当它被从B / C原子移动到的氮原子中的所有异构体，或C6在1 ，3-氮杂硼烷。这是放置在N LP在环和NH键的平面在一个有利的空间位置来充当π电子密度的受体的构象改变的结果。

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