ALKALINE HYDROLYSIS OF ALKYL ESTERS OF BENZOIC, 1- AND 2-NAPHTHOIC, 1-, 2-, AND 9-ANTHROIC, AND 1-, 2-, 3-, 4-, AND 9-PHENANTHROIC ACIDS

被引:13
作者
CORBETT, JF
FEINSTEI.A
GORE, PH
REED, GL
VIGNES, EC
机构
[1] Department of Chemistry, Brunel University
来源
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC | 1969年 / 08期
关键词
D O I
10.1039/j29690000974
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The rate coefficients for the alkaline hydrolysis of methyl carboxylic esters in ' 70% dioxan ' solution follow the sequence: 2-phenanthryl > 2-anthryl > 3-phenanthryl > phenyl > 2-naphthyl > 9-phenanthryl > 1-naphthyl > 1-phenanthryl > 1-anthryl ≫ 4-phenanthryl > 9-anthryl. A series of alkyl benzoates, and higher esters of several of the polycyclic aromatic carboxylic acids have also been studied. Electronic and steric effects on rate, on enthalpy of activation, and on entropy of activation, are discussed.
引用
收藏
页码:974 / &
相关论文
共 94 条
[1]   ALKALINE HYDROLYSIS OF POLYNUCLEAR METHYL ARYLACETATES [J].
ACTON, N ;
BERLINER, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (16) :3312-&
[2]   ETUDES CINETIQUES DANS LE DOMAINE DES DERIVES POLYCYCLIQUES AROMATIQUES .2. HYDROLYSE BASIQUE DESTERS CARBOXYLIQUES [J].
ADAMBRIERS, M ;
FIERENS, PJC ;
MARTIN, RH .
HELVETICA CHIMICA ACTA, 1955, 38 (07) :2021-2026
[3]   Phenanthrene derivatives V The Beckmann rearrangement of the oximes of acetylphenanthrenes and benzoylphenanthrenes [J].
Bachmann, WE ;
Boatner, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1936, 58 :2097-2101
[4]   On anthraquinone-carbonic acids. [J].
Barnett, ED ;
Cook, JW ;
Grainger, HH .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1924, 57 :1775-1781
[5]   CONCURRENT ALKALINE HYDROLYSIS AND ISOTOPIC OXYGEN EXCHANGE OF A SERIES OF P-SUBSTITUTED METHYL BENZOATES [J].
BENDER, ML ;
THOMAS, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (20) :4189-&
[7]  
BERKMAN YP, 1954, UKR KHIM ZH, V20, P264
[8]   RELATIVE REACTIVITIES OF POLYNUCLEAR AROMATIC SYSTEMS - THE SOLVOLYSIS OF ALPHA-ARYLETHYL CHLORIDES [J].
BERLINER, E ;
SHIEH, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (14) :3849-3854
[9]   SEPARATION OF POLAR + STERIC EFFECTS .V. KINETICS OF REACTIONS OF SUBSTITUTED BENZOIC ACIDS + RELATED CARBOXYLIC ACIDS WITH DIAZODIPHENYLMETHANE IN ETHANOL . REACTION MECHANISM IN RELATION TO PRODUCT COMPOSITION ARRHENIUS PARAMETERS + INFLUENCE OF ORTHO-SUBSTITUENTS [J].
BOWDEN, K ;
BUCKLEY, A ;
CHAPMAN, NB ;
SHORTER, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (SEP) :3380-&
[10]   SEPARATION OF POLAR + STERIC EFFECTS .4. KINETICS OF ALKALINE HYDROLYSIS OF METHYL ARYLALIPHATIC CARBOXYLATES + IONIZATION OF ARYLALIPHATIC CARBOXYLIC ACIDS [J].
BOWDEN, K ;
CHAPMAN, NB ;
SHORTER, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (SEP) :3370-&