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N-[Dichloro(methyl)silylmethyl]acetamides: synthesis and structure

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Abstract

The reaction of N-trimethylsilylacetamides with ambifunctional silane ClCH2SiMeCl2 afforded N-[dichloro(methyl)silylmethyl]-N-methylacetamide, N-[dichloro(methyl)-silylmethyl]-N-(4-methylphenyl)acetamide, and N-[dichloro(methyl)silylmethyl]-N-(4-chlorophenyl)acetamide. Multinuclear NMR spectroscopy showed that these compounds exist in solution as (O—Si)-chelates with an intramolecular C=O→Si dative bond. According to the X-ray diffraction analysis, the length of the C=O→Si dative bond in N-[dichloro(methyl)silylmethyl]-N-methylacetamide is 1.903(1) Å. In the crystal, this compound exists as a benzene solvate. The layered structure is stabilized by short Cl⋯H3C(O) and Cl⋯H3CN contacts between the axial chlorine atom and the hydrogen atoms of the amide group of the adjacent molecule (2.869 and 2.826 Å, respectively). Besides, the hydrogen atoms of the Me3Si group are involved in π-stacking interactions with the benzene molecule (l = 2.889 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

    A. S. Soldatenko, I. V. Sterkhova & N. F. Lazareva

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  1. A. S. Soldatenko
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  2. I. V. Sterkhova
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  3. N. F. Lazareva
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Corresponding author

Correspondence to N. F. Lazareva.

Additional information

All results were obtained using analytical equipment of the Baikal Analytical Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 5, pp. 1171–1177, May, 2023.

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Soldatenko, A.S., Sterkhova, I.V. & Lazareva, N.F. N-[Dichloro(methyl)silylmethyl]acetamides: synthesis and structure. Russ Chem Bull 72, 1171–1177 (2023). https://doi.org/10.1007/s11172-023-3886-y

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