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Crystals 2017, 7(1), 31;

Synthesis, Crystal Structure and DFT Studies of 1,3-Dimethyl-5-propionylpyrimidine-2,4,6(1H,3H,5H)-trione

School of Health Sciences, University of KwaZulu-Natal, Durban 4001, South Africa
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt
School of Laboratory of Medicine & Medical Sciences, University of KwaZulu-Natal, Durban 4001, South Africa
School of Chemistry and Physics, University of KwaZulu-Natal, Durban 4001, South Africa
CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Barcelona 08028, Spain
Department of Organic Chemistry, University of Barcelona, Barcelona 08028, Spain
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
Chemistry Department, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 12321, Egypt
Authors to whom correspondence should be addressed.
Academic Editor: Helmut Cölfen
Received: 17 December 2016 / Revised: 12 January 2017 / Accepted: 16 January 2017 / Published: 21 January 2017
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Novel 1,3-Dimethyl-5-propionylpyrimidine-2,4,6(1H,3H,5H)-trione was synthesized and recrystallized from ethanol. The compound was characterized by 1H NMR, 13C NMR in CDCl3, DMSO-d6 and acetone-d6, elemental analysis and X-ray diffraction. The NMR data observed that the title compound exists in the enol tautomer rather than keto, and it stabilized by strong H-bond as observed form the NMR data at different temperatures. Theoretical calculations (DFT) were carried out using Gaussian09 program package and B3LYP correlation function. Full geometry optimization of the keto and enol forms were carried out using 6-311G++(d,p) basis set. The structure and energy of the transition state between these two tautomers were calculated. The frontier orbital energy and atomic net atomic charges of the tautomers were presented. The experimental results of the title compound have been compared with the theoretical results and it was found that the experimental data are in a good agreement with the calculated values. The transition state calculations also support the stability of enol form compared to keto form at room temperature. View Full-Text
Keywords: 1,3-dimethylpyrimidine-2,4,6-trione; X-ray; DFT molecular orbital calculations; HOMO; LUMO 1,3-dimethylpyrimidine-2,4,6-trione; X-ray; DFT molecular orbital calculations; HOMO; LUMO

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Sharma, A.; Jad, Y.E.; Ghabbour, H.A.; de la Torre, B.G.; Kruger, H.G.; Albericio, F.; El-Faham, A. Synthesis, Crystal Structure and DFT Studies of 1,3-Dimethyl-5-propionylpyrimidine-2,4,6(1H,3H,5H)-trione. Crystals 2017, 7, 31.

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