ACID-CATALYZED HYDROLYSIS OF N-PHENYL-4-SUBSTITUTED-BENZOHYDROXAMIC ACIDS

被引:36
作者
GHOSH, KK
GHOSH, S
机构
[1] School of Studies in Chemistry, Pt. Ravishankar Shukla University
关键词
D O I
10.1021/jo00085a028
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acidity rate profiles have been established for the hydrolysis of some N-phenyl-4-substituted-benzohydroxamic acids 4-XC6H4(C=O)N(OH)C6H5 (X = H, CH3, OCH3, NO2, Cl, F) in sulfuric acid solutions in 20/80 (v/v) dioxane-water medium. Analysis of the data by the Cox-Yates excess acidity method and substitutent, temperature, and solvent isotope effects are all compatible with a changeover from an A-2 mechanism at low acidities to a predominantly A-1 mechanism at high acidities.
引用
收藏
页码:1369 / 1374
页数:6
相关论文
共 47 条
[1]  
AGARWAL YK, 1980, REV ANAL CHEM, V5, P3
[2]  
ALVAREZ FJ, 1987, SECONDARY SOLVENT IS, V7
[3]   A NOVEL METHOD FOR THE DETERMINATION OF IONIZATION SITES IN POLYFUNCTIONAL ACIDS AND BASES BY NMR RELAXATION RATE MEASUREMENTS [J].
BAGNO, A ;
COMUZZI, C ;
SCORRANO, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (03) :283-284
[4]  
BAGNO A, 1993, 4TH P EUR S ORG REAC
[5]   CHEMISTRY OF HYDROXAMIC ACIDS AND N-HYDROXYIMIDES [J].
BAUER, L ;
EXNER, O .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1974, 13 (06) :376-384
[6]  
BROWN DA, 1982, METAL IONS BIOL SYST, V14, pCH5
[7]   STUDIES OF AZO AND AZOXY DYESTUFFS .18. KINETICS AND MECHANISM OF THE HYDROLYSIS OF 3-(PARA'-METHOXYPHENYLAZO) AND 4-(PARA'-METHOXYPHENYLAZO)PYRIDINES IN AQUEOUS SULFURIC-ACID MEDIA [J].
BUNCEL, E ;
ONYIDO, I .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1986, 64 (11) :2115-2126
[8]  
CARPENTER BK, 1984, DETERMINATION ORG, P145
[9]   KINETICS AND MECHANISM OF THE HYDROLYSIS OF N-METHYL-N-NITROAMIDES IN AQUEOUS SULFURIC-ACID [J].
CHALLIS, BC ;
ROSA, E ;
ILEY, J ;
NORBERTO, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (01) :179-183
[10]   DONOR PROPERTIES OF HYDROXAMIC ACIDS [J].
CHATTERJEE, B .
COORDINATION CHEMISTRY REVIEWS, 1978, 26 (03) :281-303