1-Benzyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole

In the title compound, C19H15N3, the benzyl group is almost perpendicular to the triazole ring [dihedral angle = 80.64 (8)°], while the napthyl group makes an angle of 30.27 (12)° with the plane of the triazole ring. This conformation is different from the 1-benzyl-4-phenyl-1H-1,2,3-triazole analogue, which has the benzyl ring system at an angle of 87.94° and the phenyl group at an angle of 3.35° to the plane of the triazole ring.

In the title compound, C 19 H 15 N 3 , the benzyl group is almost perpendicular to the triazole ring [dihedral angle = 80.64 (8) ], while the napthyl group makes an angle of 30.27 (12) with the plane of the triazole ring. This conformation is different from the 1-benzyl-4-phenyl-1H-1,2,3-triazole analogue, which has the benzyl ring system at an angle of 87.94 and the phenyl group at an angle of 3.35 to the plane of the triazole ring.  1-Benzyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole J. I. Sarmiento-Sánchez, G. Aguirre and I. A. Rivero

Comment
In recent years, triazole compounds have received much attention due to their wide range of applications in organic and medicinal chemistry. Specifically, 1,2,3-triazoles have been used in pharmaceuticals, agrochemicals, dyes, photographic materials and corrosion inhibitors (Katritsky et al., 1996). There are numerous examples in the literature of the biological activity of triazole compounds acting as as anti-HIV agents (Alvarez et al., 1994) or as antibiotics due to their antimicrobial activity against Gram positive bacteria (Genin et al., 2000) and as selective β 3 adrenergic agonist receptors (Brockunier et al., 2000).
The molecular structure of (I) is shown in Fig. 1. The molecule shows that the phenyl group and the triazole heterocycle are linked by the methylene group. The carbon atom C13 with a C14-C13-N1 angle of 112.5 (2) o is distorted from ideal tetrahedral geometry (109.7¯). This can be attributed to steric factors of adjacent cyclic systems. Also, the bonds distances As shown in Fig. 1, the molecule shows the benzyl group is located above the plane of the triazole at a dihedral angle of 80.64 (0.08)° and the naphthyl group is at an angle fo 30.27 (0.12)°. This conformation is different from its analogue 1-benzyl-4-phenyl-1H-1, 2,3-triazole which presents the benzyl at an dihedral angle of 87.94° and the phenyl at an angle of 3.35° to the plane of the triazole (Makam & Yulin, 2004).

Experimental
All reagents were purchased in the highest quality available and were used without further purification. The solvents used in column chromatography were obtained from commercial suppliers and used without distillation. To a solution tert-BuOH/H 2 O (6 ml 1:1 v/v) was added benzyl bromide (1.684 mmol), sodium azide (1.684 mmol), 1-ethynyl-naphthalene (1.684 mmol), copper(II) sulfate (0.084 mmol, 5% mol) and sodium ascorbate (0.168 mmol, 10% mol) with vigorous stirring at 60 °C for 8 h. The reaction mixture was filtered with diatomaceous earth (kieselguhr) or zeolite and silica gel in vacuo, then extracted with ethyl acetate (60 ml). The extracts were combined and dried over anhydrous sodium sulfate. After evaporation of the solvent, the residual oil solidified and was purified by flash chromatography to give (I) (petroleum ether/ Crystallization 50 mg of (I) compound was placed for diffusion in a glass vial with chloroform-petroleum ether for one day. The crystals, suitable for data collection, were separated by filtration.

Refinement
Refinement for H atoms was carried out using a riding model, with distances constrained to: 0.93 Å for aromatic CH, 0.98 Å for methine CH. Isotropic U parameters were fixed to U iso (H)=1.2U eq (carrier atom) for aromatic CH. Fig. 1. The title compound (I) with displacement ellipsoids drawn at 30% probability level.