Benzthiazoline-2-thione (BTT) revisited: An experimental and theoretical endeavor to understand UV-spectra

Benzthiazoline-2-thione (BTT) and its derivatives are industrially and biologically important heterocyclic organic compounds. Here, we present both experimental and theoretical investigations. The IR and UV spectroscopic measurements unambiguously show the keto-enol tautomerization. Here, for the first time we report spectral changes of BTT in different solvents using quantum chemical calculations and hence reproduce both the hypsochromic and bathochromic shifts in the UV spectra which are sensitive to the nature of hydrogen bonding between solvent and BTT. Our calculations also reveal that the lowest energy transition is associated with a pi -> pi* rather than a n -> pi* transition suggested to explain experimental results. (C) 2017 Elsevier B.V. All rights reserved.