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<p>According to the NMR studies, <i>N</i>-(2-bromocyclohexyl)triflamide and <i>N</i>-(2-bromocyclohexyl)-<i>N</i>′-(triflyl)amidine exist as <i>trans</i>-isomers with equatorially oriented substituents. The quantum chemical calculations of all conformers of <i>cis</i>- and <i>trans</i>-isomers of these compounds and their fluorine-substituted analogs in the gas phase and in the solution confirm a higher stability of the experimentally proved eq-eq-conformers. No direct correlation between the H⋯X hydrogen bond length (X is halogen) and stability of the conformers (because of a lower ability of the NH group than OH to be the hydrogen bond donor) for the compounds under study and the presence of intramolecular interactions of the oxygen or fluorine atoms of the triflamide group with the hydrogen atoms of the cycle were proved by a comparison of the calculation results with those for 2-halocyclohexanols.</p>

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Configuration and conformations of N-(2-halocyclohexyl)triflamides and N-(2-halocyclohexyl)-N′-(triflyl)amidines in gas and in solution

  • 期刊论文

  • 发表日期：

    2025年9月1日

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  • A. S. Ganin,
  • M. Yu. Moskalik,
  • B. A. Shainyan,
  • S. V. Zinchenko

摘要

According to the NMR studies, N-(2-bromocyclohexyl)triflamide and N-(2-bromocyclohexyl)-N′-(triflyl)amidine exist as trans-isomers with equatorially oriented substituents. The quantum chemical calculations of all conformers of cis- and trans-isomers of these compounds and their fluorine-substituted analogs in the gas phase and in the solution confirm a higher stability of the experimentally proved eq-eq-conformers. No direct correlation between the H⋯X hydrogen bond length (X is halogen) and stability of the conformers (because of a lower ability of the NH group than OH to be the hydrogen bond donor) for the compounds under study and the presence of intramolecular interactions of the oxygen or fluorine atoms of the triflamide group with the hydrogen atoms of the cycle were proved by a comparison of the calculation results with those for 2-halocyclohexanols.