An n鈫捪€* Interaction in Aspirin: Implications for Structure and Reactivity

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• 作者：Amit Choudhary ; Kimberli J. Kamer ; Ronald T. Raines
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：October 7, 2011
• 年：2011
• 卷：76
• 期：19
• 页码：7933-7937
• 全文大小：815K
• 年卷期：v.76,no.19(October 7, 2011)
• ISSN：1520-6904

文摘

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 (蟺*) of an acceptor group. This interaction affects the physicochemical attributes of aspirin and could have implications for its pharmacology.