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Kinetics and Mechanism of Azocoupling between quaternary 1,2,4‐triazolium salts and p‐N,N‐dimethylamino benzenediazonium tetrafluoroborate

Identifieur interne : 000B82 ( Main/Curation ); précédent : 000B81; suivant : 000B83

Kinetics and Mechanism of Azocoupling between quaternary 1,2,4‐triazolium salts and p‐N,N‐dimethylamino benzenediazonium tetrafluoroborate

Auteurs : Becker ; Al Kurdi ; Mun Gwan [Corée du Sud] ; Schütz

Source :

RBID : ISTEX:5D70993E9269A444A67829D3FD81A3DEA1792BB1

Abstract

The kinetics of azocoupling between 1‐benzyl‐4‐phenyl‐, 1,3,4‐triphenyl‐, 4‐benzyl‐1‐methyl‐, 1,4‐dimethyl‐, 1,4‐diphenyl‐3‐methylmercapto‐ and 3‐benzyl‐mercapto‐1,4‐diphenyl‐1,2,4‐triazolium salts, and p‐N,N‐dimethylamino benzenediazonium tetrafluoroborate are studied spectroscopically in methanol/water 1:1 (v/v) at various pH values following up the growing‐in of the respective azodyes. The competing reactions of the diazonium salt with the solvent and the buffer (NH3/NH4Cl), and of some bleaching of the azodye formed were studied separately and accounted for in the kinetic treatment. From the pH dependence of the coupling rate constants and by application of kinetic models it turned out that not the widely accepted one‐step deprotonation mechanism of the quaternary triazolium salts applied but a two‐step mechanism comprising of pseudobase formation and their subsequent deprotonation is valid. Using the pertinent kinetic model the pK values of pseudo‐base formation (pKR+) and their deprotonation (pKA) were determined by non‐linear regression.


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DOI: 10.1002/prac.19913330102

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ISTEX:5D70993E9269A444A67829D3FD81A3DEA1792BB1

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Becker
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Al Kurdi
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Schütz
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<div type="abstract" xml:lang="en">The kinetics of azocoupling between 1‐benzyl‐4‐phenyl‐, 1,3,4‐triphenyl‐, 4‐benzyl‐1‐methyl‐, 1,4‐dimethyl‐, 1,4‐diphenyl‐3‐methylmercapto‐ and 3‐benzyl‐mercapto‐1,4‐diphenyl‐1,2,4‐triazolium salts, and p‐N,N‐dimethylamino benzenediazonium tetrafluoroborate are studied spectroscopically in methanol/water 1:1 (v/v) at various pH values following up the growing‐in of the respective azodyes. The competing reactions of the diazonium salt with the solvent and the buffer (NH3/NH4Cl), and of some bleaching of the azodye formed were studied separately and accounted for in the kinetic treatment. From the pH dependence of the coupling rate constants and by application of kinetic models it turned out that not the widely accepted one‐step deprotonation mechanism of the quaternary triazolium salts applied but a two‐step mechanism comprising of pseudobase formation and their subsequent deprotonation is valid. Using the pertinent kinetic model the pK values of pseudo‐base formation (pKR+) and their deprotonation (pKA) were determined by non‐linear regression.</div>
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