TY - JOUR

T1 - Structural similarity and similarity in thermal properties of the polymorphs: melting and crystallization from the melt of tolbutamide and chlorpropamide

AU - Drebushchak, T. N.

AU - Drebushchak, V. A.

PY - 2020/10/1

Y1 - 2020/10/1

N2 - The polymorphism of tolbutamide and chlorpropamide under melting/crystallization was investigated with using DSC and in situ X-ray powder diffraction. The asymmetry in thermal transformations was revealed for both substances. Under heating, all tolbutamide/chlorpropamide polymorphs transform into high-temperature IH/ε polymorph, which melts at 128 °C. The crystal structures of the high-temperature polymorphs, IH and ε, are very similar to each other in the unit cell parameters and in the arrangement of z-shaped infinite hydrogen-bonded ribbons. Under cooling, other polymorph crystallizes from the melt, V for tolbutamide and β for chlorpropamide, thus making easy the obtaining of these metastable polymorphs. The polymorphs of tolbutamide and chlorpropamide crystallized from their melts turned out to be also very similar to each other in their structures (space group, unit cell parameters, arrangement of π-shaped infinite hydrogen-bonded ribbons). Solid–solid transformation V ⇒ II in tolbutamide was detected both in samples stored under room conditions and those melted in capillaries, thus providing new easy way for II tolbutamide crystallization. In generalizing our results, one can expect that if evident similarity is found among the polymorphs of similar molecules in their crystal structure, the similarity in their thermal properties can be also found, and vice versa.

AB - The polymorphism of tolbutamide and chlorpropamide under melting/crystallization was investigated with using DSC and in situ X-ray powder diffraction. The asymmetry in thermal transformations was revealed for both substances. Under heating, all tolbutamide/chlorpropamide polymorphs transform into high-temperature IH/ε polymorph, which melts at 128 °C. The crystal structures of the high-temperature polymorphs, IH and ε, are very similar to each other in the unit cell parameters and in the arrangement of z-shaped infinite hydrogen-bonded ribbons. Under cooling, other polymorph crystallizes from the melt, V for tolbutamide and β for chlorpropamide, thus making easy the obtaining of these metastable polymorphs. The polymorphs of tolbutamide and chlorpropamide crystallized from their melts turned out to be also very similar to each other in their structures (space group, unit cell parameters, arrangement of π-shaped infinite hydrogen-bonded ribbons). Solid–solid transformation V ⇒ II in tolbutamide was detected both in samples stored under room conditions and those melted in capillaries, thus providing new easy way for II tolbutamide crystallization. In generalizing our results, one can expect that if evident similarity is found among the polymorphs of similar molecules in their crystal structure, the similarity in their thermal properties can be also found, and vice versa.

KW - Chlorpropamide

KW - DSC

KW - Polymorphism

KW - Tolbutamide

KW - X-ray diffraction

KW - FORM

KW - STABILITY

UR - http://www.scopus.com/inward/record.url?scp=85081289700&partnerID=8YFLogxK

U2 - 10.1007/s10973-020-09475-4

DO - 10.1007/s10973-020-09475-4

M3 - Article

AN - SCOPUS:85081289700

VL - 142

SP - 841

EP - 848

JO - Journal of Thermal Analysis and Calorimetry

JF - Journal of Thermal Analysis and Calorimetry

SN - 1388-6150

IS - 2

ER -