Abstract
Amido (A)/imido (B) tautomerism has been investigated by UV/Vis and NMR spectroscopic methods for a number of 2-acetamidothiazoles and 2-acetamidobenzothiazoles, without the use of the physical properties of “fixed parents”. The addition of polar substances to solutions of selected compounds in apolar solvents (carbon tetrachloride, dichloromethane) strongly affects the [B]/[A] ratios. Data show that the shift of the tautomeric equilibrium A/B towards the B form has two main causes: (i) increase of the polarity of the medium, and (ii) a base effect on the stabilization of the B form. The experimental ΔH and ΔS values indicate (in agreement with 1H NMR spectroscopic data) that the self-assembly of 2-acetamido derivatives is a very important factor in determining the position of the tautomeric equilibrium.
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