An n→π* Interaction in Aspirin: Implications for Structure and Reactivity

被引：66

作者：

Choudhary, Amit ^{[2
]}

Kamer, Kimberli J. ^{[1
]}

Raines, Ronald T. ^{[1
,3
]}

机构：

[1] Univ Wisconsin, Dept Biochem, Madison, WI 53706 USA

[2] Univ Wisconsin, Grad Program Biophys, Madison, WI 53706 USA

[3] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 19期

关键词：

COLLAGEN TRIPLE-HELIX; CONFORMATIONAL STABILITY; INTRAMOLECULAR CATALYSIS; PROTEIN-STRUCTURE; CRYSTAL-STRUCTURE; CHEMICAL-SHIFTS; ACID; DENSITY; SUBSTITUENTS; HYDROLYSIS;

D O I：

10.1021/jo201389d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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

引用

页码：7933 / 7937

页数：5

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