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Vasilkova N. O., Aniskov A. A., Krivenko A. P. Qualitative and Quantitative Estimation of Intramolocular Hydrogenic Communication in a Row of Orto-R-phenyl-substituted Tetrazolohexahydroquinazolines. Izvestiya of Saratov University. Chemistry. Biology. Ecology, 2018, vol. 18, iss. 1, pp. 9-?. DOI:

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Qualitative and Quantitative Estimation of Intramolocular Hydrogenic Communication in a Row of Orto-R-phenyl-substituted Tetrazolohexahydroquinazolines


The onе-pot interaction of C-aminotetrazole, cyclohexanone and o-R-benzaldehydes (in contrast to unsubstituted benzaldehyde benzaldehyde) leads to the formation of additionally linear tetrazohexahydroquinazolines, their isomers with an angular articulation of the rings. The appearance of isomers with angular articulation of the rings can be explained by the total influence of the spatial and electronic effects, and the influence of the low-energy interaction by the type of hydrogen binding NH ··R (VVS) can not be ruled out. This is confirmed by the NMR shift in the 1 H spectrum of the NH-proton singlet to a weak or strong field compared to tetrazohexahydroquinazoline, which is unsubstituted in the benzene ring. Qualitative and quantitative estimation of air force is given on the example of ortho-nitrophenyl-substituted tetrazohexahydroquinazoline. The concentration dependence of the absorption bands of stretching vibrations of the NH-bond in IR spectra in acetonitrile solution made it possible to record the air force and the MBS, the latter band disappearing upon dilution of the test solution. A similar picture was not observed for unsubstituted tetrazohexahydroquinazoline. With the help of quantum chemical calculations, a rapprochement of the nitro group and the hydrogen atom of the NH-group of the pyrimidine ring with an intermolecular depletion of 2.24 Å is determined, sufficient for the formation of the air force and its energy (12 kJ/ mol). Comparative data are given for an analogue of the tetrazolohexahydroquinazoline, which is unsubstituted in the ortho-position of the benzene ring. The obtained results allowed to substantiate the scheme for the formation of positional isomers of ortho-R-phenyltetrazolohexahydroquinazolines.


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