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New tridentate ligands based on 2-tert-butyl-4-methylphenol: synthesis and structure

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Abstract

New sterically hindered bis(3-tert-butyl-2-hydroxy-5-methylbenzyl)amine was synthesized based on 2-tert-butyl-4-methylphenol. The reaction of the latter with N, N-dimethylformamide affords N, N-bis(3-tert-butyl-2-hydroxy-5-methylbenzyl)formamide. According to the X-ray diffraction data, this reaction product occurs in the crystal as a dimer stabilized by a bifurcated hydrogen bond. The intermolecular component of the C=O⋯H-O hydrogen bond (l = 1.990 Å) between the carbonyl oxygen atom of one molecule and the phenolic hydroxy group of another molecule ensures the formation of dimers. Another component is the intramolecular C=O⋯H-O hydrogen bond (l = 1.754 Å) between the carbonyl oxygen atom and the phenolic hydroxy group of the same molecule. In the crystal, the dimers are linked via C-H…π interactions to form long chains (2.741 Å).

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Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation

    N. F. Lazareva

  2. Department of Physics, Pedagogical Institute, Irkutsk State University, 1 ul. K. Marksa, 664003, Irkutsk, Russian Federation

    E. A. Zelbst

Authors
  1. N. F. Lazareva
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Correspondence to N. F. Lazareva.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1349-1355, July, 2021.

We are grateful to A. A. Korlyukov for performing the X-ray diffraction study and preparing the cif fail for compound 4.

The results of NMR spectroscopy and elemental analysis were obtained using equipment of the Baikal Analytical Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences.

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

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Lazareva, N.F., Zelbst, E.A. New tridentate ligands based on 2-tert-butyl-4-methylphenol: synthesis and structure. Russ Chem Bull 70, 1349–1355 (2021). https://doi.org/10.1007/s11172-021-3222-3

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  • DOI: https://doi.org/10.1007/s11172-021-3222-3

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