Conformational, concomitant polymorphs of 4,4-diphenyl-2,5-cyclohexadienone: conformation and lattice energy compensation in the kinetic and thermodynamic forms

Chemistry : a European Journal
Saikat RoyGert J Kruger

Abstract

4,4-Diphenyl-2,5-cyclohexadienone (1) crystallized as four conformational polymorphs and a record number of 19 crystallographically independent molecules have been characterized by low-temperature X-ray diffraction: form A (P2(1), Z'=1), form B (P1, Z'=4), form C (P1, Z'=12), and form D (Pbca, Z'=2). We have now confirmed by variable-temperature powder X-ray diffraction that form A is the thermodynamic polymorph and B is the kinetic form of the enantiotropic system A-D. Differences in the packing of the molecules in these polymorphs result from different acidic C-H donors approaching the C=O acceptor in C-H...O chains and in synthons I-III, depending on the molecular conformation. The strength of the C-HO interaction in a particular structure correlates with the number of symmetry-independent conformations (Z') in that polymorph, that is, a short C-HO interaction leads to a high Z' value. Molecular conformation (Econf) and lattice energy (Ulatt) contributions compensate each other in crystal structures A, B, and D resulting in very similar total energies: Etotal of the stable form A=1.22 kcal mol(-1), the metastable form B=1.49 kcal mol(-1), and form D=1.98 kcal mol(-1). Disappeared polymorph C is postulated as a high-Z', high-...Continue Reading

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Jun 9, 2016·Inorganic Chemistry·Agathe Filatre-FurcateDominique Lorcy
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Oct 13, 2020·ACS Omega·Rupali G Kalshetti, Chepuri V Ramana
Jun 12, 2013·Journal of the American Chemical Society·Gautam R Desiraju

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