DETERMINATION OF THE SUBSTITUENT CONSTANT SIGMA-P FOR THE THIOAMIDE GROUP CSNH2 FROM THE IONIZATION OF ANILINES AND PHENOLS

被引：11

作者：

POLASEK, M ^{[1
]}

WAISSER, K ^{[1
]}

BOUCEK, T ^{[1
]}

机构：

[1] CHARLES UNIV, FAC PHARMACEUT, DEPT INORGAN & ORGAN CHEM, CS-50165 HRADEC KRALOVE, CZECHOSLOVAKIA

来源：

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 1991年 / 56卷 / 12期

关键词：

D O I：

10.1135/cccc19912964

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Thermodynamic ionization constants pK(a) 2.62 +/- 0.01 for the primary aromatic amino group of 4-aminothiobenzamide and pK(a) 8.28 +/- 0.01 for the phenolic hydroxy group of 4-hydroxythiobenzamide have been determined by ultra-violet spectrophotometry at 25-degrees-C. By using these pK(a) values and the Hammett equations (log K(a) vs sigma) for the ionization of fourteen 3- or 4-substituted phenols and thirteen 3- or 4-substituted anilines the substituent constant sigma(p)- = 0.68 (from the ionization of anilines) or sigma(p)- = 0.73 (from the ionization of phenols) of the thioamide group -CSNH2 was calculated.

引用

页码：2964 / 2968

页数：5

共 15 条

[1]

Albert A., 2012, DETERMINATION IONIZA

[2]

EXNER O, 1981, KORELACNI VZTAHY ORG

[3] HAMMETT SUBSTITUENT CONSTANTS FOR ELECTRON-WITHDRAWING SUBSTITUENTS - DISSOCIATION OF PHENOLS, ANILINIUM IONS AND DIMETHYLANILINIUM IONS [J].

FICKLING, MM ;

FISCHER, A ;

MANN, BR ;

PACKER, J ;

VAUGHAN, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (16) :4226-4230

[4]

GABRIEL J, 1989, CHEM PAP, V43, P389

[5] NITRILOTRIACETOHYDROXAMIC ACID, DISSOCIATION-CONSTANTS AND REACTIONS WITH CU(2+) AND FE(3+) [J].

KARLICEK, R .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1975, 40 (12) :3825-3834

[6]

KUCHAR M, 1980, VYUZITI KVANTITATIVN

[7]

PERRIN DD, 1972, DISSOCIATION C S1972

[8]

Serjeant E. P., 1979, IONISATION CONSTANTS

[9] REACTIONS OF ORGANIC COMPOUNDS WITH SODIUM HYDROSULFIDE IN LIQUID-AMMONIA .4. REACTIONS OF AROMATIC NITRILES WITH SODIUM HYDROSULFIDE IN LIQUID-AMMONIA [J].

TAKIKAWA, Y ;

TAKIZAWA, S .

NIPPON KAGAKU KAISHI, 1972, (04) :766-&

[10] ON BIOLOGICAL SIDE-EFFECTS OF POTENTIAL ANTITUBERCULOTICS .15. QUANTITATIVE RELATIONS BETWEEN CHEMICAL-STRUCTURE AND HEPATOTOXICITY OF THIOBENZAMIDES [J].

WAISSER, K ;

MACHACEK, M ;

LEBVOUA, J ;

HRBATA, J ;

DRSATA, J .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1988, 53 (11B) :2957-2961

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