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Conformational Landscape and Polymorphism in 5-Acetic Acid Hydantoin

Authors: B. A. Nogueira; G. O. Ildiz; J. Canotilho; M. E. S. Eusébio; M. S. C. Henriques; J. A. Paixão; R. Fausto

Ref.: J. Phys. Chem. A 124(31), 6303-6318 (2020)

Abstract: The conformotional space of 5-acetic acid hydantoin {5AAH; [2-(2,5-dioxoimidazolidin-4-yl)acetic acid]} was investigated by quantum chemical calculations performed at the DFT(B3LYP)/6-311++G(d,p) level of theory. A total of 13 conformers were located in the potential energy surface of the molecule, six of them bearing the carboxylic group in the cis arrangement (O═C–O–H dihedral equal to ∼0°) and the other seven possessing this group in the trans configuration (O═C–O–H dihedral equal to ∼180°). The most stable conformer (cis-I) was trapped from the gas phase into a low temperature argon matrix (10 K), and its infrared spectrum was fully assigned, also with help of results of normal coordinates’ analysis based on the DFT computed vibrational data. The electronic structure of this conformer was analyzed by using the natural bond orbital (NBO) method. The investigation of the thermal properties of 5AAH was undertaken by differential scanning calorimetry (DSC), polarized light thermal microscopy (PLTM) and Raman spectroscopy, allowing identification of five different polymorphs. Very interestingly, in the room temperature stable polymorph the molecular units of 5AAH assume the geometry of the highest-energy conformer predicted by the calculations for the isolated molecule.

DOI: 10.1021/acs.jpca.0c03789