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

Şahin O., Kantar C., Bekircan O., Şaşmaz S., Büyükgüngör O.

Jiegou Huaxue, vol.30, pp.731-737, 2011 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 30
  • Publication Date: 2011
  • Journal Name: Jiegou Huaxue
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.731-737
  • Keywords: crystal structure, chlorophenyl, triazole, hydrogen bonds, MAGNETIC-PROPERTIES, CRYSTAL-STRUCTURES, PIVALATE LIGANDS, DERIVATIVES, COMPLEXES, AGENTS, 1,2,4-TRIAZOLE, POLYMERS, PATTERNS, DENSITY
  • Recep Tayyip Erdoğan University Affiliated: Yes

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.