Identification of robust synthon in the molecular salts of 2-aminothiazole with substituted benzoic acids: A case stu

Journal of Chemical Sciences

Madhavi Oruganti²  Raghavaiah Pallepogu¹  Darshak R Trivedi1² 

[1] National Single Crystal Diffractometer Facility, University of Hyderabad, Hyderabad 500 046, India$$;Supramolecular Chemistry Laboratory, Department of Chemistry, National Institute of Technology Karnataka (NITK), Surathkal, Mangalore 575 025, India$$

关键词: Hydrogen bond;    2-aminothiazole;    dihydroxybenzoic acids;    salts;    robust synthon.;   

DOI  :  

来源: Indian Academy of Sciences

【 摘 要 】

Six new salts of an API intermediate 2-aminothiazole with different carboxylic acid coformers were synthesized and characterized by IR (Infrared spectroscopy), 1H-NMR, DSC (Differential scanning calorimetry), XRPD (X-ray powder diffraction) and single crystal XRD. The crystal structure of the salts with benzoic acid, 2,3-, 2,4-, 2,5-, 2,6- dihydroxybenzoic acids and 2,4-dinitrobenzoic acid were determined. The thiazole moiety exhibited solvent (polarity) assisted tautomerism in all reported salts and proton transfer was noticed to the ring N of thiazole due to which two point supramolecular synthon N+−H(thiazole)…O−(acid), N−H(amine)…O−(acid) was observed. The crystal structures were studied with respect to the positional effect of the competing functional groups like hydroxyl (−OH) and nitro (−NO2) as well as their donor and acceptor abilities for hydrogen bonding. The presence of the non-conventional hydrogen bond (C−H…O) has been found to play a critical role in the formation of secondary supramolecular architectures.

【 授权许可】

Unknown