KINETIC-MODEL FOR ACID-CATALYZED HYDROLYSIS OF BENZOHYDROXAMIC ACID

被引:32
作者
GHOSH, KK
RAJPUT, SK
KRISHNANI, KK
机构
[1] School of Studies in Chemistry, Ravishankar University, Raipur
关键词
D O I
10.1002/poc.610050106
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The kinetics of the hydrolysis of benzohydroxamic acid have been investigated in hydrochloric, sulphuric and perchloric acids in 10% (v/v) dimethyl sulphoxide-water at 55-degrees-C. Activation parameters were also determined. Rate correlation by the Cox-Yates excess acidity method shows an A-2 mechanism involving rapid pre-equilibrium protonation of the substrate followed by rate-limiting attack of water at the carbonyl carbon atom to form a tetrahedral intermediate which collapses, in a fast step, to the products.
引用
收藏
页码:39 / 43
页数:5
相关论文
共 25 条
[1]   ON THE RATE MAXIMA OBSERVED IN THE ACID-HYDROLYSIS OF SOME ALKYLHYDROXAMIC ACIDS [J].
BUGLASS, AJ ;
DORR, M ;
JUFFKINS, M .
TETRAHEDRON LETTERS, 1987, 28 (28) :3283-3284
[2]   ACID-CATALYSED HYDROLYSIS AND PROTONATION BEHAVIOUR OF HYDROXAMIC ACIDS [J].
BUGLASS, AJ ;
HUDSON, K ;
TILLETT, JG .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (01) :123-&
[3]   LINEAR FREE ENERGY RELATIONSHIPS CONCERNING REACTION RATES IN MODERATELY CONCENTRATED MINERAL ACIDS [J].
BUNNETT, JF ;
OLSEN, FP .
CANADIAN JOURNAL OF CHEMISTRY, 1966, 44 (16) :1917-&
[4]  
BUNTON CA, 1968, J AM CHEM SOC, V90, P1958
[5]   THE HYDROLYSES OF BENZAMIDES, METHYLBENZIMIDATIUM IONS, AND LACTAMS IN AQUEOUS SULFURIC-ACID - THE EXCESS ACIDITY METHOD IN THE DETERMINATION OF REACTION-MECHANISMS [J].
COX, RA ;
YATES, K .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (19) :2853-2863
[6]   MECHANISTIC STUDIES IN STRONG ACIDS .9. HYDROLYSIS MECHANISMS FOR ACYLHYDRAZINES IN AQUEOUS SULFURIC-ACID, DETERMINED USING THE EXCESS ACIDITY METHOD [J].
COX, RA ;
YATES, K .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (08) :1613-1617
[7]   KINETIC-EQUATIONS FOR REACTIONS IN CONCENTRATED AQUEOUS ACIDS BASED ON THE CONCEPT OF EXCESS ACIDITY [J].
COX, RA ;
YATES, K .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (22) :2944-2951
[8]   MECHANISTIC STUDIES IN STRONG ACIDS .8. HYDROLYSIS MECHANISMS FOR SOME THIOBENZOIC ACIDS AND ESTERS IN AQUEOUS SULFURIC-ACID, DETERMINED USING THE EXCESS ACIDITY METHOD [J].
COX, RA ;
YATES, K .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (24) :3061-3070
[9]   ORGANIC-REACTIONS IN SULFURIC-ACID - THE EXCESS ACIDITY METHOD [J].
COX, RA .
ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (01) :27-31
[10]  
DIFURIA F, 1982, SEPAR SCI TECHNOL, V17, P1451