N-trimetylsilyl carboxamides RC(O)NHSiMe3 (R = Me, CF3, Ph): X-ray, DFT and FTIR study

Add time:07/18/2019    Source:sciencedirect.com

The X-ray single-crystal structures of N-trimetylsilyl acetamide CH3CONHSiMe3 (1), N-trimethylsilyl trifluoroacetamide CF3CONHSiMe3 (2) and N-trimethylsilyl benzamide PhCONHSiMe3 (3) have been determined. Quantum chemical calculations (B3LYP/6-311+G**, NBO analysis) were performed for gas phase optimized structures, proton affinities and N–H bond dissociation energies of amides 1–3 and their isostructural carbon analogs 4–6. The effect of silicon atom on structural features and intermolecular electron interactions was determined. Types of self-associates which can be formed by amides 1–3 in CCl4 solution were studies by infrared spectroscopy.

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