Lucaioli, P; Nauha, E; Gimondi, I; Price, LS; Guo, R; Iuzzolino, L; Singh, I; ... Blagden, N; + view all Lucaioli, P; Nauha, E; Gimondi, I; Price, LS; Guo, R; Iuzzolino, L; Singh, I; Salvalaglio, M; Price, SL; Blagden, N; - view fewer (2018) Serendipitous isolation of a disappearing conformational polymorph of succinic acid challenges computational polymorph prediction. CrystEngComm , 20 (28) pp. 3971-3977. 10.1039/C8CE00625C.

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Abstract

A conformational polymorph (γ) of succinic acid was discovered in an attempt to purify a leucine dipeptide by cocrystallization from a methanol solution in the presence of various impurities, such as trifluoroacetic acid. The new γ form was found to have crystallized concomitantly with the most stable β form. In light of this situation, a crystal structure prediction study was undertaken to examine the polymorph landscape. These studies reveal that the γ polymorph is thermodynamically competitive with the other observed polymorphs; having a more stable folded conformation than the planar crystalline conformation in the β form, but being stabilized less by the intermolecular interactions. Simulations and experiment show that the folded conformation is dominant in solution, but that trapping long-lived crystals of the new metastable polymorph may be challenging. Thus the γ polymorph provides a stringent test of theories for predicting which thermodynamically plausible structures may be practically important polymorphs.

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