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Effect of Pressure on Two Polymorphs of Tolazamide: Why no Interconversion? Full article

Journal CrystEngComm
ISSN: 1466-8033
Output data Year: 2017, Volume: 19, Number: 16, Pages: 2243-2252 Pages count : 10 DOI: 10.1039/c6ce02527g
Tags CRYSTAL-STRUCTURE PREDICTION; ORGANIC MOLECULAR-CRYSTALS; INDUCED PHASE-TRANSITIONS; TOTAL-ENERGY CALCULATIONS; X-RAY-DIFFRACTION; WAVE BASIS-SET; L-SERINE; SINGLE-CRYSTAL; ISOENERGETIC POLYMORPHS; DIFFERENT BEHAVIOR
Authors Fedorov A.Y. 1,2 , Rychkov D.A. 1,2 , Losev E.A. 1,2 , Zakharov B.A. 1,2 , Stare J. 3 , Boldyreva E.V. 1
Affiliations
1 Institute of Solid State Chemistry and Mechanochemistry SB RAS, Kutateladze 18, Novosibirsk, 630128, Russia
2 Novosibirsk State University, Pirogova 2, Novosibirsk, 630090, Russia
3 National Institute of Chemistry, Hajdrihova 19, Ljubljana, SI-1000, Slovenia

Funding (2)

1 Russian Science Foundation 14-13-00834
2 Slovenian Research Agency P1-0012

Abstract: Two polymorphs of tolazamide, N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide, a sulfonylurea anti-diabetic drug, have different densities and molecular packings. Polymorph II converts into polymorph I in the solid state on heating or via recrystallization if solvent-assisted. The effect of pressure on the two forms and the possibility of a transformation to a denser form on compression have been studied. No phase transitions have been observed in either of the forms in a pentane-isopentane mixture (when no recrystallization is possible). Polymorph II recrystallized partly into a denser polymorph I in methanol at 0.1 GPa, but the transformation stopped at an early stage. Solid state DFT calculations of the two forms as well as conformational landscape investigation in the gas phase were used to rationalize this result. The anisotropic pressure-induced strain of the two polymorphs has been compared in relation to changes in the hydrogen bond geometry and the behavior of stacking interactions.
Cite: Fedorov A.Y. , Rychkov D.A. , Losev E.A. , Zakharov B.A. , Stare J. , Boldyreva E.V.
Effect of Pressure on Two Polymorphs of Tolazamide: Why no Interconversion?
CrystEngComm. 2017. V.19. N16. P.2243-2252. DOI: 10.1039/c6ce02527g WOS Scopus РИНЦ AN OpenAlex
Files: Full text from publisher
Dates:
Submitted: Dec 8, 2016
Accepted: Mar 27, 2017
Published print: Apr 1, 2017
Published online: Apr 6, 2017
Identifiers:
Web of science: WOS:000399764000013
Scopus: 2-s2.0-85018477120
Elibrary: 41773011
Chemical Abstracts: 2017:568341
OpenAlex: W2604546457
Citing:
DB Citing
Web of science 31
Scopus 31
OpenAlex 28
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