Mechanism of the hydrolysis of α-(p-nitrophenyl)cinnamonitrile derivatives

被引：0

作者：

Pyun, S.-Y. ^{[1
]}

Kim, T.-R.

Kwon, H.-S.

Lee, S.-H.

机构：

[1] Pukyong Natl Univ, Dept Chem, Pusan 608739, South Korea

[2] Korea Univ, Dept Chem, Seoul 136701, South Korea

[3] Chungbuk Natl Univ, Coll Educ, Korea Dept Chem Educ, Chonju 360763, South Korea

[4] Pukyong Natl Univ, Dept Chem Engn, Pusan 608739, South Korea

来源：

KINETICS AND CATALYSIS | 2007年 / 48卷 / 05期

关键词：

D O I：

10.1134/S0023158407050047

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The rate constant hydrolysis of alpha-(p-nitrophenyl)cinnamonitrile(NCPN) and its derivatives have been determined at various pH, and the rate equation which can be applied over a wide pH range is obtained. On the basis of the rate equation, hydrolysis product, general base, and substituent effects, a plausible mechanism of hydrolysis has been proposed: At pH < 4.0, the hydrolysis was initiated by the addition of water to beta-carbon of the carbon-carbon double bond. At pH > 8.5, the addition of hydroxide ion to the double bond was rate controlling. In the range of pH 4.0-8.5, these two reactions occurred competitively.

引用

页码：626 / 631

页数：6

共 37 条

[1] FORMATION OF CYTOTOXIC ALDEHYDE ACROLEIN DURING IN-VITRO DEGRADATION OF CYCLOPHOSPHAMIDE [J].

ALARCON, RA ;

MEIENHOF.J .

NATURE-NEW BIOLOGY, 1971, 233 (42) :250-&

[2]

BERGMANN ED, 1959, ORG REACTIONS, V10, P191

[3] NUCLEOPHILIC-ADDITION TO OLEFINS .18. KINETICS OF THE ADDITION OF PRIMARY AMINES AND ALPHA-EFFECT NUCLEOPHILES TO BENZYLIDENE MELDRUMS ACID [J].

BERNASCONI, CF ;

MURRAY, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (17) :5251-5257

[4] KINETICS OF HYDROLYSIS OF BENZYLIDENEACETYLACETONE [J].

BERNASCONI, CF ;

KANAVARIOTI, A ;

STRONACH, MW .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14) :3806-3813

[5] NUCLEOPHILIC-ADDITION TO OLEFINS .12. SOLVENT-INDUCED CHANGE IN THE RATE-LIMITING STEP OF THE HYDROLYSIS OF BENZYLIDENEMALONONITRILE IN ACIDIC ME2SO-WATER SOLUTION [J].

BERNASCONI, CF ;

KANAVARIOTI, A ;

KILLION, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (12) :3612-3620

[6] NUCLEOPHILIC-ADDITION TO OLEFINS .14. KINETICS OF THE REACTION OF 1,3-INDANDIONE ANION WITH BENZYLIDENE-1,3-INDANDIONE [J].

BERNASCONI, CF ;

LAIBELMAN, A ;

ZITOMER, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (23) :6570-6575

[7] RATE OF PROTONATION OF 2,6-DI-TERT-BUTYLPYRIDINE BY THE HYDRONIUM ION - STERIC HINDRANCE TO PROTON-TRANSFER [J].

BERNASCONI, CF ;

CARRE, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (10) :2707-2709

[8] NUCLEOPHILIC ADDITIONS TO OLEFINS .23. HIGH INTRINSIC RATE-CONSTANT AND LARGE IMBALANCES IN THE THIOLATE ION ADDITION TO SUBSTITUTED ALPHA-NITROSTILBENES [J].

BERNASCONI, CF ;

KILLION, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7506-7512

[9] NUCLEOPHILIC-ADDITION TO OLEFINS .6. STRUCTURE REACTIVITY RELATIONSHIPS IN THE REACTIONS OF SUBSTITUTED BENZYLIDENE MELDRUMS ACIDS WITH WATER, HYDROXIDE ION, AND ARYL OXIDE IONS [J].

BERNASCONI, CF ;

LEONARDUZZI, GD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (19) :5133-5142

[10] NUCLEOPHILIC-ADDITION TO OLEFINS .25. KINETICS OF HYDROLYSIS OF SUBSTITUTED BETA-NITROSTYRENES - TRANSITION-STATE IMBALANCES AND INTRINSIC RATE CONSTANTS FOR 3 DIFFERENT TYPES OF NITRONATE ION FORMING PROCESSES - RELEVANCE TO THE NITROALKANE ANOMALY [J].

BERNASCONI, CF ;

PASCHALIS, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (15) :5893-5902

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