‘Hedvall effect’ in cryogrinding of molecular crystals. A case study of a polymorphic transition in chlorpropamide

Drebushchak, T. N.; Ogienko, A. G.; Boldyreva, Elena V.

doi:10.1039/c1ce05189j

Cited by 31 publications

(25 citation statements)

References 35 publications

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“…This transformation was also observed on cryogrinding. 37 The most stable high-temperature polymorphs of both tolbutamide (I H ) and chlorpropamide (ε) undergo reversible conformational isostructural transformations into their lowtemperature metastable daughter forms (I L and ε′, respectively), albeit at different temperatures: 313 K for I L ⇔ I H (see Fig. 3) and ∼215 K for ε′ ⇔ ε (see Fig.…”

Section: Comparing the Polymorphs Of Tolbutamide And Chlorpropamidementioning

confidence: 99%

Single-crystal to single-crystal conformational polymorphic transformation in tolbutamide at 313 K. Relation to other polymorphic transformations in tolbutamide and chlorpropamide

Drebushchak

Pankrushina³

et al. 2016

CrystEngComm

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Three polymorphs of tolbutamide (I L , II, and III) were studied using single-crystal X-ray diffraction, from 100 K to room temperature (forms II and III) and to 350 K (form I), and differential scanning calorimetry. The reversible transformation, I L ⇔ I H , was found to be of the single-crystal to single-crystal type and the structure of the high-temperature form (I H) was solved and refined. The structure of I H differs from that of I L only in the conformation of the molecule, with molecular arrangements being practically unchanged (isostructural conformational transformation). The transition takes place at 313 K with no sign of hysteresis. The volume change, ΔV/V, across the reversible transformation I L ⇔ I H was calculated and compared to those for the other conformational transformations. Two types of conformational polymorphic transformations (irreversible reconstructive and reversible isostructural) in tolbutamide and chlorpropamide were compared.

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Section: Comparing the Polymorphs Of Tolbutamide And Chlorpropamidementioning

confidence: 99%

Single-crystal to single-crystal conformational polymorphic transformation in tolbutamide at 313 K. Relation to other polymorphic transformations in tolbutamide and chlorpropamide

Drebushchak

Pankrushina³

et al. 2016

CrystEngComm

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“…On cooling, chlorpropamide undergoes reversible phase transitions into the low-temperature forms II , III and " 0 (Drebushchak et al, 2009), which can be obtained on cooling the crystals of the corresponding polymorphs from ambient conditions down to $257, < 150 and < 200 K, respectively. The low-temperature phase transition of "-chlorpropamide into the " 0 form was shown to account for an " to polymorph transformation on cryogrinding (Drebushchak, Ogienko & Boldyreva, 2011).…”

Section: Introductionmentioning

confidence: 99%

A high-pressure polymorph of chlorpropamide formed on hydrostatic compression of the α-form in saturated ethanol solution

Seryotkin

Drebushchak

Boldyreva

2013

Acta Crystallogr Sect B

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The crystal structure of the high-pressure polymorph ( 0 ) of an antidiabetic drug, chlorpropamide [4-chloro-N-(propylaminocarbonyl)benzenesulfonamide, C 10 H 13 ClN 2 O 3 S], which is formed at $ 2.8 GPa from the -polymorph (P2 1 2 1 2 1 ) on hydrostatic compression in saturated ethanol solution, has been determined. As a result of the phase transition, the a, c and parameters change jumpwise, whereas the changes in b parameter are continuous through the phase transition point. The high-pressure form is monoclinic (P2 1 11) and has Z 0 equal to 2, the two independent molecules differing in their conformations. The hydrogen bonds expand slightly in the high-pressure polymorph after the transition, and this expansion is interrelated with the changes in molecular conformations enabling a denser packing. The transition is reversible, but the crystal quality deteriorates as a result of multiple compression-decompression cycles, and a pseudomerohedral twinning accompanies the transformation.

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“…This was to be expected given the response of each material to humid summer atmosphere, and highlights the influence of humidity on mechanochemical reactions as well as the accelerating effect of grinding on solid state processes. In contrast, conducting these same grinding processes under a dry atmosphere in a glove box or in winter 47 (<20% RH) resulted in no, or only traces of transformation ( Fig. 4 and ESI †).…”

Section: -56mentioning

confidence: 93%

“…47 It has been documented for some other organic molecular crystals that different types of treatment (such as shear or impact) may have different or even opposing effects on a transformation. 48,49 It is therefore important to compare the outcome of the transformations on different types of mechanical treatment.…”

Section: Introductionmentioning

confidence: 99%

Polymorphism of chlorpropamide on liquid-assisted mechanical treatment: choice of liquid and type of mechanical treatment matter

et al. 2018

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Different types of mechanical treatment (tableting, grinding, milling, etc.) are important technological operations in the pharmaceutical industry. Solid materials are not merely comminuted during such treatment, but can undergo polymorphic transitions and amorphisation. A liquid is often added to the solid sample on purpose, e.g. in order to facilitate comminution. In many cases, liquid is present inadvertently, either as a result of trace solvent following up-stream operations, or sorbed from the atmosphere. This work explores the liquid-assisted mechanical treatment of two metastable forms of a model pharmaceutical compound chlorpropamide (CPA), namely the β-and ε-forms. We investigate the stability of these polymorphs to mechanical treatment in the presence of a series of fluids that have affinity for different fragments of the CPA molecule. In addition to variation in fluids, the effect of different mechanical treatment is explored, employing model shear and restricted impact devices, alongside grinding in a mortar. CPA offers a clear example of the drastically different results of shear and impact on mechanochemical polymorphism, on the importance of the careful selection of solvent for liquid-assisted treatment, and on the possible role of even trace quantities of solvent. Further, this work demonstrates the importance of the starting polymorph in determining the outcome of a mechanochemical process. All of these factors can have notable consequence on the outcome of technological operations that include mechanical treatment.

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‘Hedvall effect’ in cryogrinding of molecular crystals. A case study of a polymorphic transition in chlorpropamide

Cited by 31 publications

References 35 publications

Single-crystal to single-crystal conformational polymorphic transformation in tolbutamide at 313 K. Relation to other polymorphic transformations in tolbutamide and chlorpropamide

Single-crystal to single-crystal conformational polymorphic transformation in tolbutamide at 313 K. Relation to other polymorphic transformations in tolbutamide and chlorpropamide

A high-pressure polymorph of chlorpropamide formed on hydrostatic compression of the α-form in saturated ethanol solution

Polymorphism of chlorpropamide on liquid-assisted mechanical treatment: choice of liquid and type of mechanical treatment matter

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