Structural and energetic characterization of the tautomers 2-benzothiazolinone and 2-hydroxybenzothiazole

• Type: Article in International Scientific Journal
• Date: 2014

Authors

Ana L R Silva (Author) Other; Victor M F Morais (Author) Other; Maria D M C R Ribeiro da Silva (Author) FCUP

Journal

Title: Journal of Molecular Structure

Vol. 1078

Pages: 197-206

ISSN: 0022-2860

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 9 Citations

Scopus - 11 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-009-X8Q

DOI: 10.1016/j.molstruc.2014.05.043

Abstract (EN): This work reports an experimental and computational thermochemical study for 2-benzothiazolinone. The standard (p degrees = 0.1 MPa) molar energy of combustion of this compound was measured by rotating bomb combustion calorimetry. The standard molar enthalpy of the corresponding transition from crystalline to gaseous phases, at T = 298.15 K, was obtained from high temperature Calvet microcalorimetry measurements. The experimental results enable the calculation of the standard molar enthalpy of formation of the compound, in the gaseous state, at T = 298.15 K. The gas-phase enthalpies of formation of the title compounds, 2-benzothiazolinone and its enol form 2-hydroxybenzothiazole, were estimated computationally from high-level oh initio molecular orbital calculations at the G3(MP2)//B3LYP level of theory. The computed value for the keto form compares very well with the experimental result obtained in this work. The hydroxy <-> oxo tautomerism of the title compounds was explored in this work as it may be relevant to their ability to occur as different polymorphic forms.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 10