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Two New Proton Transfer Salts of Benzo[d]thiazol-2-amine with Different Aromatic Acids

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Abstract

Two new proton transfer salts (HABT)+(SA)− (1) and (HABT)+2(ADSA)2−·2H2O (2) were synthesized from the reaction of benzo[d]thiazol-2-amine (2-aminobenzothiazole) (ABT) with 2-hydroxybenzoic acid (salicylic acid) (HSA) and 2-aminobenzene-1,4-disulfonic acid (H2ADSA), respectively. The molecular structures of these salts were carried out by elemental analysis, X-ray diffraction crystallography, FTIR and UV–Vis techniques Single-crystal X-ray analysis of the compounds revealed proton transfer from acidic moieties to basic moieties to form salts with intermolecular hydrogen bond motifs R22(8) for 1 and R33(10) for 2. The intramolecular hydrogen bond creates the cyclic S(6) motif in both structures (1 and 2). For salt 1, crystallization took place in the P2(1)/c space group of the monoclinic system, and for salt 2 in the P-1 space group of the triclinic system. The antibacterial and antifungal properties of the compounds are assayed against various Gram positive bacteria {Bacillus subtilis, Listeria monocytogenes (ATCC 7644), Enterococcus faecalis (ATCC 29212), Staphylococcus aureus (NRRL B-767)}, Gram negative bacteria {Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853)} and fungus {Candida albicans (F89)}. Minimum inhibitory concentrations (MIC) of synthesized salts were compared with antibacterial (levofloxacin cefepime, vancomycin) and antifungal (Fluconazole) reference compounds.

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Data Availability

CCDC 2178935 (1) and CCDC 2178938 (2) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk (the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax (+ 44 1123 336 033; e.mail: deposit@ccdc.cam.ac.uk or http://www.ccdc.cam.ac.uk). The authors declare that all other data supporting the findings of this study are available within the article and its supplementary information files.

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Acknowledgements

The authors acknowledge to Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8-QUEST diffractometer.

Funding

We thank to Kütahya Dumlupınar University Research Foundation (Project No: 2021-42) for providing support for this study.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Science, Kütahya Dumlupınar University, 43100, Kutahya, Turkey

    Nurgün Büyükkıdan, Halil İlki̇men & Seher Kaya

  2. Department of Physics Education, Faculty of Education, Gazi University, 06100, Ankara, Turkey

    Musa Sarı

  3. Department of Food Engineering, Faculty of Agricultural Engineering, Eskişehir Osmangazi University, 26000, Eskisehir, Turkey

    Aysel Gülbandılar

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  1. Nurgün Büyükkıdan
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Correspondence to Nurgün Büyükkıdan.

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Büyükkıdan, N., İlki̇men, H., Kaya, S. et al. Two New Proton Transfer Salts of Benzo[d]thiazol-2-amine with Different Aromatic Acids. J Chem Crystallogr 53, 336–344 (2023). https://doi.org/10.1007/s10870-022-00974-w

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