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Synthesis, structure, and dynamic behavior in solution of arylamino-1,3,5-triazines

1. Unsymmetrically substituted arylamino-1,3,5-triazines

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Russian Chemical Bulletin Aims and scope

Abstract

Ten unsymmetrically substituted arylamino-1,3,5-triazines were synthesized and studied by dynamic NMR spectroscopy. The free energies of the hindered rotation ΔG ≠?are in 59–77 kJ mol− 1 range. Using difference-mode NOE NMR experiments, the structures of the major and minor rotation isomers were proved. The DFT B3LYP/6-31G* calculations were performed. The difference between the calculated rotation barriers and the experimental values obtained by line shape analysis is less than 7.6 kJ mol−1. The height of the rotation barrier varies in a 18 kJ mol−1 range depending on the substituents in the triazine ring.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    P. A. Belyakov & Yu. A. Strelenko

  2. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    A. V. Shastin

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  1. P. A. Belyakov
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  2. A. V. Shastin
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2366–2376, October, 2005.

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Belyakov, P.A., Shastin, A.V. & Strelenko, Y.A. Synthesis, structure, and dynamic behavior in solution of arylamino-1,3,5-triazines. Russ Chem Bull 54, 2441–2451 (2005). https://doi.org/10.1007/s11172-006-0135-0

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  • DOI: https://doi.org/10.1007/s11172-006-0135-0

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