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Crystals 2016, 6(5), 56;

Comparisons between Crystallography Data and Theoretical Parameters and the Formation of Intramolecular Hydrogen Bonds: Benznidazole

Instituto de Ciências Ambientais e Desenvolvimento Sustentável, Universidade Federal da Bahia, Barreiras, Bahia 47808-021, Brazil
Colegiado de Farmácia, Universidade Federal do Vale do São Francisco, Petrolina, Pernambuco 56304-917, Brazil
Departamento de Química, Universidade Federal da Paraíba, João Pessoa, Paraíba 58036-300, Brazil
Author to whom correspondence should be addressed.
Academic Editor: Sławomir J. Grabowski
Received: 1 February 2016 / Revised: 29 April 2016 / Accepted: 4 May 2016 / Published: 12 May 2016
(This article belongs to the Special Issue Analysis of Hydrogen Bonds in Crystals)
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The conformational preferences of benznidazole were examined through the application of DFT, PCM and QTAIM calculations, whose results were compared with crystallography data. The geometries were fully optimized with minimum potential energy surface by means of the Relaxed Potential Energy Surface Scan (RPESS) at AM1, followed by the B3LYP/6-311++G(d,p) theoretical level. As a result, the s-cis conformation (1C) was shown to be more stable (4.78 kcal∙mol−1) than s-trans (1T). The Quantum Theory Atoms in Molecules (QTAIM) was applied in order to characterize the (N–H∙∙∙O=N) and (C–H∙∙∙=N) intramolecular hydrogen bonds. The simulation of solvent effect performed by means of the implicit Polarized Continuum Model (PCM) revealed great results, such as, for instance, that the conformation 1W is more stable (23.17 kcal∙mol−1) in comparison to 1C. Our main goal was stressed in the topological description of intramolecular hydrogen bonds in light of the QTAIM approach, as well as in the solvent simulation to accurately obtain an important conformation of benznidazole. View Full-Text
Keywords: benznidazole; hydrogen bond; crystal structure benznidazole; hydrogen bond; crystal structure

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Oliveira, B.G.; Filho, E.B.A.; Vasconcellos, M.L.A.A. Comparisons between Crystallography Data and Theoretical Parameters and the Formation of Intramolecular Hydrogen Bonds: Benznidazole. Crystals 2016, 6, 56.

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