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Abstract
The tautomerism of benzoxazoline-2-thione (BOT; thio- keto) and 2-mercaptobenzoxazole (MBO; thio- enol) has been thoroughly investigated by means of Raman (3600–100 cm −1), infrared (4000–200 cm −1), 1H and 13C NMR spectra and X-ray powder diffraction (XRD). In addition, temperature-dependent 1H NMR spectra from −90 to +90 °C were acquired. To complement experimental results with theoretical predictions, we performed Density Functional Theory (DFT) calculations utilizing B3LYP, B3PW91 and SVWN methods at 6-31G(d) basis set. Both computational and spectral results were in favor of thio- keto BOT structure with no evidence for the existence of thio- enol (MBO) tautomer which firmly eliminates the possibility of an existing equilibrium between keto and enol forms. Moreover the dimerization percentage of thio- keto benzoxazoline-2-thione (BOT) and benzothiazoline-2-thione (BTT) were found to be 11.9% and 2.5%, respectively which favors strong hydrogen bonding interactions in BOT. Aided by normal coordinate analysis, force constants in internal coordinates and potential energy distributions (PEDs), a complete vibrational assignment for all fundamentals was obtained. The results are compared with the sulfur analogue, benzothiazoline-2-thione (BTT) whenever appropriate.
Published Version
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