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Reactivity of 5-nitro-2,1-benzothiazole-3-diazonium hydrogensulfate towards OH and CH acids: structure, spectral properties, tautomerism

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Abstract

5-Nitro-2,1-benzothiazole-3-diazonium ion reacts with various substrates (phenol, 2-naphthol, mesitylene, acetone, acetylacetone, ethyl acetoacetate) to give corresponding azo or hydrazo compounds. Characterization of the prepared compounds by means of multinuclear magnetic resonance, X-ray diffraction, and HRMS together with the study of acidobasic properties is presented, as well as significant solvatochromism.

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Acknowledgments

Authors are indebted to the Faculty of Chemical Technology, University of Pardubice for institutional support. Authors also would like to acknowledge Dr. Miloslav Kincl from Joint Laboratory of Solid State Chemistry of IMC ASCR v.v.i. and University of Pardubice, Faculty of Chemical Technology for the measurement of IR spectra.

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Authors and Affiliations

  1. Institute of Organic Chemistry and Technology, University of Pardubice, Pardubice, Czech Republic

    Vladimír Macháček, Eva Horáková, Petr Šimůnek, Jakub Valtr & Břetislav Brož

  2. Dipartimento di Scienze Chimiche e Farmaceutiche, Centro di Strutturistica Diffrattometrica, Università di Ferrara, Ferrara, Italy

    Valerio Bertolasi

Authors
  1. Vladimír Macháček
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  2. Eva Horáková
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  3. Petr Šimůnek
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  4. Jakub Valtr
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  5. Valerio Bertolasi
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  6. Břetislav Brož
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Corresponding author

Correspondence to Petr Šimůnek.

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Dedicated to the memory of Prof. Josef Přikryl on the occasion of his 67th birthday.

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Macháček, V., Horáková, E., Šimůnek, P. et al. Reactivity of 5-nitro-2,1-benzothiazole-3-diazonium hydrogensulfate towards OH and CH acids: structure, spectral properties, tautomerism. Monatsh Chem 147, 1765–1777 (2016). https://doi.org/10.1007/s00706-016-1793-8

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  • DOI: https://doi.org/10.1007/s00706-016-1793-8

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