DISSOCIATION-CONSTANTS OF SUBSTITUTED PHENOLS AND HOMOCONJUGATION CONSTANTS OF THE CORRESPONDING PHENOL PHENOLATE SYSTEMS IN ACETONITRILE

被引：35

作者：

MAGONSKI, J ^{[1
]}

PAWLAK, Z ^{[1
]}

JASINSKI, T ^{[1
]}

机构：

[1] UNIV GDANSK,INST CHEM,PL-80952 GDANSK,POLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS | 1993年 / 89卷 / 01期

关键词：

D O I：

10.1039/ft9938900119

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：

Dissociation constants of 25 phenols and homoconjugation constants of 14 phenol-phenolate systems in acetonitrile have been determined from emf measurements. From these results a linear relationship log K(a)AN = 1.9 pK(a)H2O + 8.3 has been derived. Stronger homoconjugation of weaker proton donors has been found to be a result of various (steric, inductive, mesomeric, charge delocalization) effects; however, the increase of homoconjugation constants with electron density at the phenolic oxygen seems to be unquestionable. Ten hydrogen bis-phenolates were prepared to complete this study, some of which crystallized well from water.

引用

页码：119 / 122

页数：4

共 25 条

[1]

BHIGGS AJ, 1956, T FARADAY SOC, V52, P35

[2] ADDITIVE SUBSTITUENT EFFECTS ON THERMODYNAMIC FUNCTIONS OF PROTON IONIZATION PROCESSES .3. PHENOLS WITH ADJACENT METHYL AND CHLORO-SUBSTITUENTS [J].