Kinetics of Substitution of 4-Methoxyphenylazo Groups of 2,6-Dioxo-5(3)-(4-methoxyphenylazo)-3(5)-(4-methoxyphenylhydrazono)-1,2,3,6-tetrahydropyridine-4-carboxylic Acid by Reaction with 4-Nitrobenzenediazonium Cation

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Title:Kinetics of Substitution of 4-Methoxyphenylazo Groups of 2,6-Dioxo-5(3)-(4-methoxyphenylazo)-3(5)-(4-methoxyphenylhydrazono)-1,2,3,6-tetrahydropyridine-4-carboxylic Acid by Reaction with 4-Nitrobenzenediazonium Cation
Creators:
Horáčková, Jaroslava
Štěrba, Vojeslav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 59, 7, pp. 1665-1672

Abstract

<p>Kinetics have been studied of gradual replacement of 4-methoxyphenylazo groups in 2,6-dioxo-5(3)-(4-methoxyphenylazo)-3(5)-(4-methoxyphenylhydrazono)-1,2,3,6-tetrahydropyridine-4-carboxylic acid (<i>IIIa</i>) by 4-nitrophenylazo groups using the reaction with 4-nitrobenzenediazonium cation (<i>IIc</i>) in acetate and phosphate buffers. The rate constant of replacement of the second methoxyphenylazo group is lower by a factor of ca 60. From the experimentally found p<i>K</i><sub>a</sub> values of the corresponding azohydrazone compounds with methoxy, chloro, or nitro substituent at 4-position (<i>IIIa</i> - <i>IIIf</i>) it has been concluded that the 5(3)-(4-methoxyphenylazo)-3(5)-(4-nitrophenylhydrazono) derivative is formed in the first step.

Title:Kinetics of Substitution of 4-Methoxyphenylazo Groups of 2,6-Dioxo-5(3)-(4-methoxyphenylazo)-3(5)-(4-methoxyphenylhydrazono)-1,2,3,6-tetrahydropyridine-4-carboxylic Acid by Reaction with 4-Nitrobenzenediazonium Cation
Creators:
Horáčková, Jaroslava
Štěrba, Vojeslav
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:59
Number:7
Page Range:pp. 1665-1672
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19941665UNSPECIFIED
ID Code:589
Item Type:Article
Deposited On:06 Feb 2009 17:02
Last Modified:06 Feb 2009 16:02

Citation

Horáčková, Jaroslava; Štěrba, Vojeslav (1994) Kinetics of Substitution of 4-Methoxyphenylazo Groups of 2,6-Dioxo-5(3)-(4-methoxyphenylazo)-3(5)-(4-methoxyphenylhydrazono)-1,2,3,6-tetrahydropyridine-4-carboxylic Acid by Reaction with 4-Nitrobenzenediazonium Cation. Collection of Czechoslovak Chemical Communications, 59 (7). pp. 1665-1672. ISSN 0010-0765

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