Spectroscopic Studies and Crystal Structure of 4-(2-Hydroxy-3-Methoxybenzylideneamino)-N-(5-Methylisoxazol-3-yl) Benzenesulfonamide

• Published in: Journal of chemical crystallography 2010-08, Vol.40 (8), p.691-695
• Main Authors: Yıldız, Mustafa, Ünver, Hüseyin, Erdener, Diğdem, İskeleli, Nazan Ocak
• Format: Article
• Language: English
• Subjects: Chemistry; Chemistry and Materials Science; Crystallography and Scattering Methods; Inorganic Chemistry; Organometallic Chemistry; Original Paper; Physical Chemistry
• ISSN: 1074-1542; 1572-8854
• DOI: 10.1007/s10870-010-9723-9

Schiff base 4-[(2-hydroxy-3-methoxybenzylideneamino)- N -(5-methylisoxazol-3-yl)benzene-sulfonamide has been synthesized from the reaction of 4-amino- N -(5-methylisoxazol-3-yl)benzenesulfonamide(sulfamethoxazole) with 2-hydroxy-3-methoxybenzaldehyde. It has been characterized by elemental analysis, MS, IR, 1 H NMR, 13 C NMR, HETCOR and UV–Visible techniques. The structure of it also has been examined crystallographically. For the compound exist as dominant form of enol-imines in both the solid state and the solutions. It crystallizes in the monoclinic space group P 2 1 / c with a  = 8.2694(7), b  = 8.3453(5), c  = 26.260(2) Å, β = 97.142(7) °, V  = 1798.1(2) Å 3 , D x  = 1.431 g cm −3 , R 1  = 0.0529 and wR 2  = 0.1370 [ I  > 2σ( I )], respectively. Index Abstract The tautomerism in the Schiff base ligands plays an important role for distinguishing their photochromic and thermochromic characteristics. Both phenomena is associated with a proton transfer (enol-imine, O–H···N, keto-amine, O···H–N).