Tautomeric properties and crystal structure of N-[2-hydroxy-1-naphthylidene]2,5-dichloroaniline by M. Yildiz, H. Ünver, D. Erdener, N. Ocak, A. Erdönmez, and T. Nuri Durlu

Crystal Research and Technology

Cryst. Res. Technol. 41, 600 (2006) - Abstract -

Tautomeric properties and crystal structure of N-[2-hydroxy-1-naphthylidene]2,5-dichloroaniline

M. Yildiz, H. Ünver*, D. Erdener, N. Ocak**, A. Erdönmez**, and T. Nuri Durlu*

Department of Chemistry, Faculty of Science and Arts, Canakkale Onsekiz Mart University, TR-17100 Canakkale, Turkey
*Department of Physics, Faculty of Science, Ankara University, TR-06100 Tandogan-Ankara, Turkey
**Department of Physics, Faculty of Science and Arts, Ondokuz Mayýs University, TR-55139 Kurupelit, Turkey

Keywords	crystal structure, tautomerism, spectroscopic studies, UV-visible, FT-IR
PACS	61.66.Hq
DOI	10.1002/crat.200510632

The title compound has been synthesised by the reaction of 2-hydroxy-1-naphthaldehyde with 2,5-dichloroaniline. The compound was characterized by elemental analysis, IR and UV-Visible techniques. The UV-Visible spectra of the Schiff base with OH group in ortho position to the imino group was studied in polar and nonpolar solvents in acidic and basic media. The structure of compound has been examined cyrstallographically. It crystallizes in the orthorhombic space group P2₁2₁2₁ with a =6.059(1), b = 12.105(2) c = 20.006(2) Å, V = 1467.4(3) Å³, D_x = 1.431 g^.cm^-3 and Z = 4. The crystal structure was solved by direct methods and refined by full-matrix least squares. Molecule of the title compound N-[2-hydroxy-1-naphthylidene]2,5-dichloroaniline is nearly planar. The molecule contains a strong intramolecular N…H-O hydrogen bond between the imine and hydroxyl group [O1 and N1 = 2.540(4) Å].

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