Kinetics of Coupling of 4-Methoxybenzenediazonium Ion with 2,6-Dihydroxypyridine

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Title:Kinetics of Coupling of 4-Methoxybenzenediazonium Ion with 2,6-Dihydroxypyridine
Creators:
Horáčková, Jaroslava
Štěrba, Vojeslav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 6, pp. 951-956
Uncontrolled Keywords:Dissociation constant, Azo coupling reaction, Chemical kinetics, Electrophilic aromatic substitution

Abstract

The kinetics of reaction of 4-methoxybenzenediazonium ion (<strong>3</strong>) with 2,6-dihydroxypyridine (<strong>1</strong>) has been studied in methoxyacetate, acetate, and phosphate buffers. The rate-limiting step is the formation of the reaction intermediate and not the splitting off of the proton (which was detected in the cases of citrazinic acid and its methyl ester). Therefrom it follows that for 2,6-dihydroxypyridine derivatives the steric hindrance to the formation of the Wheland intermediate exerted by CO<sub>2</sub><sup>-</sup> and CO<sub>2</sub>CH<sub>3</sub> groups represents a necessary condition for the rate-limiting splitting off of the proton and, hence, for the existence of general base catalysis.

Title:Kinetics of Coupling of 4-Methoxybenzenediazonium Ion with 2,6-Dihydroxypyridine
Creators:
Horáčková, Jaroslava
Štěrba, Vojeslav
Uncontrolled Keywords:Dissociation constant, Azo coupling reaction, Chemical kinetics, Electrophilic aromatic substitution
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:61
Number:6
Page Range:pp. 951-956
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19960951UNSPECIFIED
ID Code:997
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:05

Citation

Horáčková, Jaroslava; Štěrba, Vojeslav (1996) Kinetics of Coupling of 4-Methoxybenzenediazonium Ion with 2,6-Dihydroxypyridine. Collection of Czechoslovak Chemical Communications, 61 (6). pp. 951-956. ISSN 0010-0765

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