Cannazza, Giuseppe, Carrozzo, Marina M., Battisti, Umberto, Braghiroli, Daniela, Parenti, Carlo, Troisi, Alessandro and Troisi, Luigino. (2010) Determination of kinetic parameters of enantiomerization of benzothiadiazines by DCXplorer. Chirality, Vol.22 (No.9). pp. 789-797. ISSN 0899-0042

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Abstract

Benzothiadiazines differently substituted at the sulfonamidic nitrogen atom, at the stereogenic carbon atom and at the anilinic nitrogen atom have been synthesized and fully characterized. Enantioseparation of these compounds has revealed rapid on-column enantiomerization. The recently developed software DCXplorer has been successfully applied to calculate enantiomerization kinetic parameters. Enantiomerization barriers of 3-phenyl substituted benzothiadiazines, calculated in this work, have indicated a higher enantiomerization rate suggesting that the aromatic substituent exerts a strong effect on the enantiomerization process. Methyl substitution on N-2 position led to higher free energy barriers of enantiomerization, suggesting negative influence of methyl in the N-2 position on enantiomerization kinetics. However, methylation on N-4 position increases the enantiomerization rates significantly. The results obtained have been employed to postulate an enantiomerization mechanism for chiral benzothiadiazine type compounds. Chirality 22:789-797, 2010. (C) 2010 Wiley-Liss, Inc.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry R Medicine > RS Pharmacy and materia medica
Divisions:	Faculty of Science > Chemistry Faculty of Science > Centre for Scientific Computing
Library of Congress Subject Headings (LCSH):	Racemization, High performance liquid chromatography, Chirality
Journal or Publication Title:	Chirality
Publisher:	John Wiley & Sons, Inc.
ISSN:	0899-0042
Date:	October 2010
Volume:	Vol.22
Number:	No.9
Number of Pages:	9
Page Range:	pp. 789-797
Identification Number:	10.1002/chir.20838
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access
Funder:	Italy. Ministero dell'istruzione, dell'università e della ricerca [ Ministry of Education, Universities and Research (Italy)] (MIUR)
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URI:	http://wrap.warwick.ac.uk/id/eprint/5311

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