N-Methyl-N,N-bis(Silatranylmethyl)amine: Structure and reactivity

Abstract

Trimethylsilylacetonitrile Me3SiCH2CN and N-methyl-N,N-bis(silatranylmethyl)amine hygrohalogenide were obtained by the interaction of N-methyl-N,N-bis(silatranylmethyl)amine MeN[CH2Si(OCH2CH2)3N]21 with MeCN/Me3SiX (X = Cl, I). The key stage of this reaction is the formation of the intermolecular complexes between amine 1 and Me3SiX. The alkylation of amine 1 by ICH2SiX3 (SiX3 = SiMe3, Si(OMe)3 and Si(OCH2CH2)3N) give rise to the generation of the corresponding ammonium salts {(X3SiCH2)MeN[CH2Si(OCH2CH2)3N]2}+I-. The molecular structures of N-methyl-N,N-bis(silatranylmethyl)amine (1), N-methyl-N-[(trimethylsilyl)methyl]-N,N-bis(silatranylmethyl)ammonium iodide (4) and N-methyl-N-N,N-tris(silatranylmethyl)ammonium iodide (6) were determined by single-crystal X-ray diffraction. Compound 1 exists as mix of the conformers 1A (values lN→Si are equal 2.212 Å and 2.274 Å), 1B (values of lN→Si are equal 2.252 Å and 2.272 Å) and 1C (values lN→Si are equal 2.273 Å and 2.291 Å). The length of dative bond N→Si of molecules 1A-1C is longer than in molecules 4 and 6 (Δl lie between 0.105 Å and 0.199 Å), but length of Si–CH2 bond is shorter on 0.001–0.034 Å.