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

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Abstract

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, 1H NMR, 13C 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 P21/c with a = 8.2694(7), b = 8.3453(5), c = 26.260(2) Å, β = 97.142(7) °, V = 1798.1(2) Å3, 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).

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science and Arts, Çanakkale Onsekiz Mart University, 17100, Çanakkale, Turkey

    Mustafa Yıldız & Diğdem Erdener

  2. Department of Physics, Faculty of Science, Ankara University, 06100, Tandoğan, Ankara, Turkey

    Hüseyin Ünver

  3. Department of Physics, Faculty of Science and Arts, Ondokuz Mayıs University, 55139, Kurupelit, Samsun, Turkey

    Nazan Ocak İskeleli

Authors
  1. Mustafa Yıldız
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  2. Hüseyin Ünver
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  3. Diğdem Erdener
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  4. Nazan Ocak İskeleli
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Correspondence to Mustafa Yıldız.

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Yıldız, M., Ünver, H., Erdener, D. et al. Spectroscopic Studies and Crystal Structure of 4-(2-Hydroxy-3-Methoxybenzylideneamino)-N-(5-Methylisoxazol-3-yl) Benzenesulfonamide. J Chem Crystallogr 40, 691–695 (2010). https://doi.org/10.1007/s10870-010-9723-9

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