Structural investigations into the beta-effect of pentavalent silicon

Abstract

Ester and ether derivatives of 2-[(8-dimethylaminonaphthalen-1-yl) dimethylsilanyl]ethanol (10a) were prepared as part of a preliminary study to determine the β-effect of pentavalent silicon. The p-nitrobenzoate, 3,5-dinitrobenzoate, and o-nitrobenzoates ester derivatives 10e-10g, which were characterized using X-ray crystallography, showed partial distortion of the silicon toward a trigonal bipyramidal geometry with the peri-nitrogen occupying one of the apical sites. The second apical site is occupied by a CH3 substituent in 10e and 10f, while the CH2CH2OR substituent occupies the apical position in 10g. The C-OR bond distances in these structures were lengthened compared to standard value..