Model studies of the histidine-tyrosine cross-link in cytochrome c oxidase reveal the flexible substituent effect of the imidazole moiety

被引：41

作者：

Pratt, DA ^{[1
]}

Pesavento, RP ^{[1
]}

van der Donk, WA ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 13期

关键词：

D O I：

10.1021/ol050916g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Experimental and theoretical studies were carried out to interrogate the effect of an imidazole substituent in each of the ortho, meta, and para positions on the pK(a), E degrees, and O-H BDE of phenol. The results reveal that imidazole substitution lowers the pK, of phenol and increases the E degrees of phenoxide due to its sigma-electron withdrawing ability (sigma(-)(p) = +0.21, sigma(-)(m) = +0.45) but decreases the O-H BDE and E degrees of phenol due to its T-electron-donating ability (sigma(+)(p) = -0.45).

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页码：2735 / 2738

页数：4

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