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Synthesis and Structure of N ‐Silylated Anilines
Author(s) -
Mitzel Norbert W.,
Angermaier Klaus,
Schmidbaur Hubert
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941270509
Subject(s) - chemistry , triethylamine , heteronuclear molecule , aryl , benzene , silanes , crystal structure , crystallography , medicinal chemistry , base (topology) , stereochemistry , nuclear magnetic resonance spectroscopy , organic chemistry , alkyl , silane , mathematical analysis , mathematics
The new N ‐(arylsilyl)anilines 1–5 have been obtained by the reaction of aryl(halo)silanes with the corresponding anilines in the presence of the auxiliary base triethylamine. The benzene parts of the anilines have been chosen such that their fluoro, methyl, and methoxy substituents exert different electronic effects. The molecular structures of the monosilylated anilines 3 and 4 have been determined by single‐crystal X‐ray diffraction analysis. The coordination geometry of the nitrogen atoms have been found to be planar. Heteronuclear NMR spectra ( 1 H, 13 C, 15 N, 29 Si) have been recorded and the structural results correlated with the one‐bond coupling constant 1 J ( 29 Si 15 N).