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Synthesis, NMR structural characterization and molecular modeling of substituted thiosemicarbazones and semicarbazones using DFT calculations to prove the syn/anti isomer formation
Author(s) -
Venkatachalam T. K.,
Pierens Gregory K.,
Reutens David C.
Publication year - 2014
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.4041
Subject(s) - chemistry , semicarbazone , molecule , density functional theory , proton nmr , dimethyl sulfoxide , carbon 13 nmr , computational chemistry , nmr spectra database , stereochemistry , molecular model , organic chemistry , spectral line , physics , astronomy
Thiosemicarbazones possessing electron‐donating and electron‐withdrawing groups were prepared, and their spectral characteristics determined. In all cases, the spectra showed that one isomer was formed, allowing further functionalization to molecules of biological interest. We provide NMR data for some of the thiosemicarbazones and semicarbazones. We also provide evidence that for 2‐pyridyl thiosemicarbazone, the syn isomer slowly converts into the anti isomer in dimethyl sulfoxide solvent with first‐order kinetics. Molecular modeling and density functional theory calculations confirmed these observations. Copyright © 2014 John Wiley & Sons, Ltd.