OXIDATION POTENTIAL AS A MEASURE OF THE EFFECT OF ENVIRONMENT ON THE REACTIVITY OF ANIONIC NUCLEOPHILES

被引：17

作者：

NIYAZYMBETOV, ME ^{[1
]}

EVANS, DH ^{[1
]}

机构：

[1] UNIV DELAWARE,DEPT CHEM & BIOCHEM,NEWARK,DE 19716

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1993年 / 07期

关键词：

D O I：

10.1039/p29930001333

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The irreversible anodic peak potential of anionic nucleophiles has been shown to be linearly correlated with various measures of their nucleophilic reactivity, including rates of S(N)2 and S(N)Ar reactions as well as addition to Michael acceptors. The correlations incorporate both changes in the nature of the solvent and the identity of the counter ion. The nucleophiles considered were iodide, azide, cyanide, 4-cyanophenolate, the anion of 2-mercaptobenzoxazole and the anion of ethyl nitroacetate. It is suggested that the oxidation potential can be used as an easily measurable predictor of the effect of solution environment on nucleophilic reactivity.

引用

页码：1333 / 1338

页数：6

共 27 条

[1]

BAIZER MM, 1991, ORGANIC ELECTROCHEMI, P1265

[2]

Bard A.J., 1980, ELECTROCHEMICAL METH, Vsecond

[3] ORGANOMETALLIC ELECTROCHEMISTRY .7. NUCLEOPHILICITIES OF METALLIC AND METALLOIDAL ANIONS DERIVED FROM METALS OF GROUPS 4,5,6,7, AND 8 [J].