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Abstract.1 Reactions of nucleophilic substitution between 5-R-2,3-dichloro-1,4-naphthoquinones and 4-amino-5-heteryl-4H-1,2,4-triazoles-3-thiols were carried out. It is shown that the interaction can take place in two alternative ways and the reaction direction is controlled by reaction conditions. Search of differences in atoms reactivity in investigated molecules by comparing the calculated Fukui atonic indices was conducted. The influence of electron donor and electron acceptor substituent in 2,3-dichloro-1,4-naphthoquinone 5 th position on the nucleophilic substitution reaction regioselectivity was shown experimentally. Comparison of obtained 1 H NMR spectra with DFT calculated for both possible isomers of obtained products allowed to uniquely attribute synthesized compounds to relevant structures. The synthesized compounds were characterized by IR, 1 H NMR, 13C NMR spectroscopy and elemental analysis.