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Determination of kinetic parameters of enantiomerization of benzothiadiazines by DCXplorer
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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. doi:10.1002/chir.20838 ISSN 0899-0042.
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Official URL: http://dx.doi.org/10.1002/chir.20838
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 | ||||
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Subjects: | Q Science > QD Chemistry R Medicine > RS Pharmacy and materia medica |
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry Faculty of Science, Engineering and Medicine > Science > Centre for Scientific Computing |
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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 | ||||
Official Date: | October 2010 | ||||
Dates: |
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Volume: | Vol.22 | ||||
Number: | No.9 | ||||
Number of Pages: | 9 | ||||
Page Range: | pp. 789-797 | ||||
DOI: | 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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