4-Amino-3-(p-chlorophenyl)-5-(p-methoxybenzyl)-4H-1,2,4-triazole: X-ray and DFT-calculated Structures


Onur S., Cihan K., Olcay B., Selami S., Orhan B.

CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, vol.30, no.5, pp.731-737, 2011 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 30 Issue: 5
  • Publication Date: 2011
  • Title of Journal : CHINESE JOURNAL OF STRUCTURAL CHEMISTRY
  • Page Numbers: pp.731-737

Abstract

The title compound, 4-amino-3-(p-chlorophenyl)-5-(p-methoxybenzyl)-4H-1,2,4-triazole I, C16H15ClN4O), has been determined using X-ray diffraction techniques and the molecular structure has also been optimized at the B3LYP/6-31 G(d, p) level using density functional theory (DFT). The triazole ring exhibits dihedral angles of 41.61(15)degrees and 80.73(11)degrees with the phenyl rings. The molecules are linked principally by N-H center dot center dot center dot N hydrogen bonds involving the amino NH2 group and a triazole N atom, forming C(5) chains which are further linked to give a two-dimensional network of molecules. The N-H center dot center dot center dot N hydrogen bonding is supported by C-H center dot center dot center dot N hydrogen bond and C-H center dot center dot center dot pi interaction. Intermolecular N-H center dot center dot center dot N and C-H center dot center dot center dot N hydrogen bonds produce R-2(2)(9), R-4(4)(10) and R-4(4)(20) rings.