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

Büyükkıdan N., İlki̇men H., Kaya S., SARI M., GÜLBANDILAR A.

Journal of Chemical Crystallography, 2022 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Publication Date: 2022
  • Doi Number: 10.1007/s10870-022-00974-w
  • Journal Name: Journal of Chemical Crystallography
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Keywords: 2-Aminobenzothiazole, Antimicrobial activity, Hydrogen bond motif, Salt, X-ray
  • Gazi University Affiliated: Yes


© 2022, The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.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. Graphical Abstract: [Figure not available: see fulltext.].