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Vol. 27 No. 3 (2015): Vol 27 Issue 3

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Synthesis, Crystal Structure and DFT Studies of 4-(1-Benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-6-(o-tolyl)pyrimidin-2-amine

https://doi.org/10.14233/ajchem.2015.17818
S. Murugavel
Department of Physics, Thanthai Periyar Government Institute of Technology, Vellore-632 002, India
R. Madhanraj
Department of Physics, Ganadipathy Tulsi's Jain Engineering College, Kaniyambadi, Vellore-632 102, India
Sangaraiah Nagarajan
Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai-625 021, India
Alagusundaram Ponnuswamy
Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai-625 021, India

Corresponding Author(s) : S. Murugavel

smurugavel27@gmail.com

Asian Journal of Chemistry, Vol. 27 No. 3 (2015): Vol 27 Issue 3

Abstract

The compound (I), 4-(1-benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-6-(o-tolyl)pyrimidin-2-amine (C21H20N6), was synthesized and structurally characterized by elemental analysis, 1H NMR and 13C NMR and single crystal X-ray diffraction. The compound crystallizes as a colourless needle shaped in the monoclinic system, space group P21/n with cell constants: a = 11.2942(16) Å, b = 16.1209(18) Å, c = 10.6253(14) Å, a = g = 90°, b = 106.898 (5)°, V = 1851 (4) Å3, Z = 4. In the compound, the triazole and the pyrimidine rings are essentially planar. The molecular conformation is stabilized by an intramolecular C-H…N hydrogen bond, which generates an S(6) ring motif. The crystal packing is stabilized by intermolecular N-H…N and C-H…p hydrogen bonds thereby generating a three-dimensional supramolecular network. The molecular geometry was also optimized using density functional theory using (DFT/B3LYP) method with the 6-311G (d, p) basis set and compared with the experimental data.

Keywords

X-ray structure determination Hydrogen bonds DFT calculations
Murugavel, S., Madhanraj, R., Nagarajan, S., & Ponnuswamy, A. (2015). Synthesis, Crystal Structure and DFT Studies of 4-(1-Benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-6-(o-tolyl)pyrimidin-2-amine. Asian Journal of Chemistry, 27(3), 974–978. https://doi.org/10.14233/ajchem.2015.17818
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