N,N-Bis(Silylmethyl)anilines: Synthesis and structure

https://doi.org/10.1016/j.jorganchem.2022.122438

The novel N,N-bis(silylmethyl)anilines PhN(CH2SiX3)2 were obtained by the reaction of N-(silylmethyl)anilines PhNHCH2SiX3 with chloromethylsilanes ClCH2SiX3 (SiX3 = SiMe3, Si(OMe)3). Their ammonium salts were prepared by the alkylation of N,N-bis(silylmethyl)anilines with MeI. The transetherification of N,N-bis[(trimethoxysilyl)methyl]aniline with triethanolamine led to the formation of N,N-bis(silatranylmethyl)aniline Ph[CH2Si(OCH2CH2)3N]2. Its molecular structure was determined by single crystal X-ray diffraction. It has been found that two solvates having slightly different molecular structures Ph[CH2Si(OCH2CH2)3N]2•MeCN and 3Ph[CH2Si(OCH2CH2)3N]2•3.24 MeCN were formed as result of the recrystallization of N,N-bis(silatranylmethyl)aniline from MeCN. The geometrical parameters of silatranyl groups Si(OCH2CH2)3N in these solvates are closely and the lengths of dative bonds N→Si lie between 2.164(3) Å and 2.168(3) Å in the typical range for silatranyl groups. In crystals of these solvates there are a big voids which vary in size and shape.