Electrochemically controlled hydrogen bonding. Nitrobenzenes as simple redox-dependent receptors for arylureas

被引：82

作者：

Bu, JJ ^{[1
]}

Lilienthal, ND ^{[1
]}

Woods, JE ^{[1
]}

Nohrden, CE ^{[1
]}

Hoang, KT ^{[1
]}

Truong, D ^{[1
]}

Smith, DK ^{[1
]}

机构：

[1] San Diego State Univ, Dept Chem & Biochem, San Diego, CA 92182 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 17期

关键词：

D O I：

10.1021/ja0462272

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reduction of nitrobenzene derivatives in the presence of arylureas in aprotic solvents results in large positive shifts in potential of the nitrobenzene(o/-) cyclic voltammetry wave with little change in wave shape. This behavior is indicative of reversible hydrogen bonding between nitrobenzene radical anions and arylureas. Computer fitting of the cyclic voltammetry of 4-nitroaniline, NA, plus 1,3-diphenylurea in DMF shows essentially no binding between urea and NA in the oxidized state (K-ox < 1 M-1), but very strong binding in the reduced state (K-red = 8 x 10(4) M-1), along with very rapid rates of hydrogen bond formation (k(I)'s approximate to 10(8)-10(10) M-1 s(-1)), making this system a fast on/off redox switch.

引用

页码：6423 / 6429

页数：7

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