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Deuterium Isotope Effects in 13C NMR Spectra of Intramolecularly Hydrogen-Bonded Salicylaldehyde-4-phenylthiosemicarbazone

The structure of salicylaldehyde-4-phenylthiosemicarbazone (1) has been studied by using NMR and DFT methods. It was demonstrated that in DMSO-d6 and CD2Cl2 solution the molecule existed primarily in the localized hydroxy-thione tautomeric form and that there was no proton transfer at the ambient temperature. Partially deuterated molecule was prepared and deuterium isotope effects (DIE) on 13C chemical shifts were measured and analyzed. DIEs have also pointed towards the hydroxy-thione form as the dominant form in solution. Moreover, changes in DIEs and in chemical shifts observed in different solvents have pointed towards interactions of 1 and solvent molecules via intermolecular hydrogen bonding in addition to the existing intramolecular interactions.

salicylaldehyde-4-phenylthiosemicarbazone; hydrogen bonds; deuterium isotope effects; NMR; DFT

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