Spectroscopic Determination of Acid Dissociation Constants of N-Substituted-6-acylbenzothiazolone Derivatives

The acid dissociation constants of twelve novel drug precursor N-substituted-6-acylbenzothiazolone derivatives were determined by using the UV–vis spectroscopic technique. The protonation and deprotonation behaviors of the investigated molecules were researched from the super basic to super acid reg...

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Bibliographic Details
Published inThe journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Vol. 115; no. 20; pp. 5112 - 5117
Main Authors Gülseven Sıdır, Yadigar, Sıdır, İsa, Berber, Halil
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 26.05.2011
Subjects
A: Kinetics, Spectroscopy
Acids - chemistry
Benzothiazoles - chemical synthesis
Benzothiazoles - chemistry
Hydrogen-Ion Concentration
Molecular Structure
Spectrophotometry, Ultraviolet - instrumentation
Stereoisomerism
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Summary:The acid dissociation constants of twelve novel drug precursor N-substituted-6-acylbenzothiazolone derivatives were determined by using the UV–vis spectroscopic technique. The protonation and deprotonation behaviors of the investigated molecules were researched from the super basic to super acid regions (i.e., 8 mol·L–1 KOH to 98% H2SO4) including the pH region. It is observed that all of the molecules are protonated in the super acidic region. The calculated relative stability values of possible tautomer structures indicate that the keto form of investigated molecules is favored over the enol form. It was predicted that protonation occurs at the amide (oxo) group found in the keto form.
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ISSN:1089-5639
1520-5215
DOI:10.1021/jp2018549