Kinetics and Mechanism of Cyclization of N-(2-Methoxycarbonylphenyl)-N-methylsulfonamide to 1-Methyl-(1H)-2,1,3-benzothiadiazine-4(3H)-one-2,2-dioxide

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Title:Kinetics and Mechanism of Cyclization of N-(2-Methoxycarbonylphenyl)-N-methylsulfonamide to 1-Methyl-(1H)-2,1,3-benzothiadiazine-4(3H)-one-2,2-dioxide
Creators:
Kaválek, Jaromír
Macháček, Vladimír
Sedlák, Miloš
Štěrba, Vojeslav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 57, 6, pp. 1282-1290

Abstract

The cyclization kinetics of <i>N</i>-(2-methoxycarbonylphenyl)-<i>N</i>-methylsulfonamide to 1-methyl-(1<i>H</i>)-2,1,3-benzothiadiazine-4(3<i>H</i>)-one-2,2-dioxide have been studied in glycinamide, morpholine, and butylamine buffers and in solutions of potassium hydroxide. The rate-limiting step consists in splitting off of the proton from the cyclic intermediate formed from the anion of the starting substrate. The value of the Bronsted coefficient β decreases with increasing p<i>K</i><sub>a</sub> value of the conjugate acid of buffer. The calculated p<i>K</i><sub>a</sub> value of the cyclic intermediate is 9.3.

Title:Kinetics and Mechanism of Cyclization of N-(2-Methoxycarbonylphenyl)-N-methylsulfonamide to 1-Methyl-(1H)-2,1,3-benzothiadiazine-4(3H)-one-2,2-dioxide
Creators:
Kaválek, Jaromír
Macháček, Vladimír
Sedlák, Miloš
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:57
Number:6
Page Range:pp. 1282-1290
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19921282UNSPECIFIED
ID Code:106
Item Type:Article
Deposited On:06 Feb 2009 16:39
Last Modified:06 Feb 2009 15:40

Citation

Kaválek, Jaromír; Macháček, Vladimír; Sedlák, Miloš; Štěrba, Vojeslav (1992) Kinetics and Mechanism of Cyclization of N-(2-Methoxycarbonylphenyl)-N-methylsulfonamide to 1-Methyl-(1H)-2,1,3-benzothiadiazine-4(3H)-one-2,2-dioxide. Collection of Czechoslovak Chemical Communications, 57 (6). pp. 1282-1290. ISSN 0010-0765

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