A DFT study of the chemical reactivity of thiobencarb and its oxidized derivatives in aqueous phase

Luis Humberto Mendoza-Huizar


In the present work, the global and local reactivity of S-4-chlorobenzyl N, N-diethylthiocarbamate (TB) and its oxidized derivatives (sulfone (TBSu) and sulfoxide (TBS) was analyzed. Also, the chemical reactivity of the dechlorinated forms of TB (DTB), TBSu (DTBSu) and TBs (DTBs) was studied. The calculations were performed at the wB97XD/6-311++G(2d,2p) level of theory in the aqueous phase. The condensed Fukui functions indicate that for TB and DTB the most preferred sites for donating electron in a reaction are located in the S and N atoms, while the most reactive sites for accepting electrons are associated with the aromatic ring (AR). For TBS and DTBS, the more reactive sites are located on AR, S and AR for nucleophilic, electrophilic and free radical attacks, respectively. In the case of TBSu and DTBSu, the AR result to be the more reactive zone for the three kind of attacks. Last results suggest that the cleavage of the C–S bond in TB, TBS and their dechlorinated forms is favored by electrophilic attacks. Additionally, our results suggest that in TB is plausible the cleavage of the C-N favored by electrophiles attacking on this molecule.


thiobencarb; Fukui function; dual descriptor; DFT

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DOI: https://doi.org/10.2298/JSC170927034M

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