A TEMPERATURE-DEPENDENT CHANGE IN THE MECHANISM OF ACID CATALYSIS OF THE HYDROLYSIS OF PARA-NITROPHENYL BETA-D-GLUCOPYRANOSIDE INDICATED BY O-18 AND SOLVENT DEUTERIUM KINETIC ISOTOPE EFFECTS

被引:23
作者
BENNET, AJ [1 ]
DAVIS, AJ [1 ]
HOSIE, L [1 ]
SINNOTT, ML [1 ]
机构
[1] UNIV BRISTOL,DEPT ORGAN CHEM,CANTOCKS CLOSE,BRISTOL BS8 1TS,AVON,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1987年 / 05期
关键词
D O I
10.1039/p29870000581
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:581 / 584
页数:4
相关论文
共 24 条
[1]   INTERMOLECULAR GENERAL-ACID CATALYSIS IN ACETAL HYDROLYSIS [J].
ANDERSON, E ;
CAPON, B .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1969, (08) :1033-&
[2]  
BELL RP, 1973, PROTON CHEM, P293
[3]   O-18 AND SECONDARY H-2 KINETIC ISOTOPE EFFECTS CONFIRM THE EXISTENCE OF 2 PATHWAYS FOR ACID-CATALYZED HYDROLYSES OF ALPHA-ARABINOFURANOSIDES [J].
BENNET, AJ ;
SINNOTT, ML ;
WIJESUNDERA, WSS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1985, (08) :1233-1236
[4]   COMPLETE KINETIC ISOTOPE EFFECT DESCRIPTION OF TRANSITION-STATES FOR ACID-CATALYZED HYDROLYZES OF METHYL ALPHA-GLUCOPYRANOSIDES AND BETA-GLUCOPYRANOSIDES [J].
BENNET, AJ ;
SINNOTT, ML .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (23) :7287-7294
[5]  
BERGSON G, 1977, CHEM SCRIPTA, V11, P25
[6]  
CAPON B, 1963, TETRAHEDRON LETT, P911
[7]  
Conchie J., 1963, METHODS CARBOHYDR CH, V2, P345
[8]   MECHANISM AND CATALYSIS FOR HYDROLYSIS OF ACETALS, KETALS, AND ORTHO-ESTERS [J].
CORDES, EH ;
BULL, HG .
CHEMICAL REVIEWS, 1974, 74 (05) :581-603
[9]   GENERAL ACID CATALYSIS AND PH-INDEPENDENT HYDROLYSIS OF 2-(PARA-NITROPHENOXY)TETRAHYDROPYRAN [J].
FIFE, TH ;
BROD, LH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (06) :1681-&
[10]   The relation between the rates of some acid catalyzed reactions and the acidity function, H-o [J].
Hammett, LP ;
Paul, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1934, 56 :830-832