Synthesis and crystal structures of N,2,4,6-tetramethylanilinium trifluoromethanesulfonate and N-isopropylidene-N,2,4,6-tetramethylanilinium trifluoromethanesulfonate

Two 2,4,6-trimethylaniline-based trifuloromethanesulfonate (trifluoromethanesulfonate) salts were synthesized and characterized by single-crystal X-ray diffraction. N,2,4,6-Tetramethylanilinium trifluoromethanesulfonate, [C10H14NH2+][CF3O3S − ] (1), was synthesized via methylation of 2,4,6-trimethylaniline. N-Isopropylidene-N,2,4,6-tetramethylanilinium trifluoromethanesulfonate, [C13H20N+][CF3O3S − ] (2), was synthesized in a two-step reaction where the imine, N-isopropylidene-2,4,6-trimethylaniline, was first prepared via a dehydration reaction to form the Schiff base, followed by methylation using methyl trifluoromethanesulfonate to form the iminium ion. In compound 1, both hydrogen bonding and π – π interactions form the main intermolecular interactions. The primary interaction is a strong N — H...O hydrogen bond with the oxygen atoms of the trifluoromethanesulfonate anions bonded to the hydrogen atoms of the ammonium nitrogen atom to generate a one-dimensional chain. The [C10H14NH2+] cations form dimers where the benzene rings form a π – π interaction with a parallel-displaced geometry. The separation distance between the calculated centroids of the benzene rings is 3.9129   (8)   Å , and the interplanar spacing and ring slippage between the dimers are 3.5156   (5) and 1.718   Å , respectively. For 2, the [C13H20N+] cations also form dimers as in 1, but with the benzene rings highly slipped. The distance between the calculated centroids of the benz...
Source: Acta Crystallographica Section E - Category: Chemistry Authors: Tags: crystal structure iminium ion ammonium ion trifluoromethanesulfonate 2 – 4,6-trimethylaniline methylation N,2,4,6-tetramethylanilinium N-isopropylidene-N,2,4,6-tetramethylanilinium research communications Source Type: research
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