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N-acyl tetrahydrothienopyridine derivatives serve as important structural motifs in bioorganic chemistry. Restricted rotation of C-N bond in such molecules gives rise to two distinct chemical environments. Thienopyridine derivatives 4a-4i were synthesized and characterised by 1H and 13C NMR spectroscopy. The NMR spectra reveal a doubling of signals, which suggests the presence of two rotamers in the solution. Variable temperature (VT) 1H-NMR studies supported this hypothesis. The NOESY analysis confirmed that Z-rotamer is present in major form as compared to E-rotamer. The results were further corroborated through density functional theoretic calculations.
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