阿司匹林中的 n→π* 相互作用：对结构和反应性的影响。
An n→π* interaction in aspirin: implications for structure and reactivity.
机构信息
Graduate Program in Biophysics, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.
出版信息
J Org Chem. 2011 Oct 7;76(19):7933-7. doi: 10.1021/jo201389d. Epub 2011 Sep 6.
Abstract
Stereoelectronic effects modulate molecular structure, reactivity, and conformation. We find that the interaction between the ester and carboxyl moieties of aspirin has a previously unappreciated quantum mechanical character that arises from the delocalization of an electron pair (n) of a donor group into the antibonding orbital (π*) of an acceptor group. This interaction affects the physicochemical attributes of aspirin and could have implications for its pharmacology.
摘要
立体电子效应调节分子结构、反应性和构象。我们发现，阿司匹林的酯基和羧基之间的相互作用具有以前未被认识到的量子力学特性，这是由于供电子基团的一对电子（n）离域到受电子基团的反键轨道（π*）中。这种相互作用影响了阿司匹林的物理化学性质，可能对其药理学有影响。
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