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Isoenergetic Polymorphism: The Puzzle of Tolazamide as a Case Study Full article

Journal Chemistry - A European Journal
ISSN: 0947-6539 , E-ISSN: 1521-3765
Output data Year: 2015, Volume: 21, Number: 43, Pages: 15395-15404 Pages count : 10 DOI: 10.1002/chem.201501541
Tags calorimetry, crystal growth, density functional calculations, polymorphism, X-ray diffraction
Authors Boldyreva E.V. 1,2 , Arkhipov S.G. 1,2 , Drebushchak T.N. 1,2 , Drebushchak V.A. 2,3 , Losev E.A. 1,2 , Matvienko A.A. 1,2 , Minkov V.S. 1,2 , Rychkov D.A. 1,2 , Seryotkin Y.V. 1,2,3 , Stare J. 4 , Zakharov B.A. 1,2
Affiliations
1 Institute of Solid State Chemistry, Mechanochemistry SB RAS, 18 Kutateladze str., Novosibirsk, Russian Federation
2 Novosibirsk State University, 2 Pirogov str., Novosibirsk, Russian Federation
3 Institute of Geology and Mineralogy, 3 Koptyuga pr., Novosibirsk, Russian Federation
4 National Institute of Chemistry, 19 Hajdrihova str., Ljubljana, Slovenia

Abstract: In the present case study of tolazamide we illustrate how many seemingly contradictory results that have been obtained from experimental observations and theoretical calculations can finally start forming a consistent picture: a "puzzle put together". For many years, tolazamide was considered to have no polymorphs. This made this drug substance unique among the large family of sulfonylureas, which was known to be significantly more prone to polymorphism than many other organic compounds. The present work employs a broad and in-depth analysis that includes the use of optical microscopy, single-crystal and powder X-ray diffraction, IR and Raman spectroscopies, DSC, semiempirical PIXEL calculations and DFT of three polymorphs of tolazamide. This case study shows how the polymorphs of a molecular crystal can be overlooked even if discovered serendipitously on one of numerous crystallizations, and how very different molecular packings can be practically isoenergetic but still crystallize quite selectively and transform one into another irreversibly upon heating.
Cite: Boldyreva E.V. , Arkhipov S.G. , Drebushchak T.N. , Drebushchak V.A. , Losev E.A. , Matvienko A.A. , Minkov V.S. , Rychkov D.A. , Seryotkin Y.V. , Stare J. , Zakharov B.A.
Isoenergetic Polymorphism: The Puzzle of Tolazamide as a Case Study
Chemistry - A European Journal. 2015. V.21. N43. P.15395-15404. DOI: 10.1002/chem.201501541 WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
Submitted: Apr 21, 2015
Published online: Sep 4, 2015
Published print: Oct 19, 2015
Identifiers:
Web of science: WOS:000363332200042
Scopus: 2-s2.0-84944711137
Elibrary: 24962784
Chemical Abstracts: 2015:1475121
Chemical Abstracts (print): 163:526750
OpenAlex: W2135165706
Citing:
DB Citing
Web of science 26
Scopus 25
OpenAlex 25
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