Abstract
BackgroundNovel mono N-alkyl quaternary ammonium salts (3a-f) were prepared using the Menschutkin reaction from the cage adamanzane type aminal 1,3,6,8-tetraazatricyclo[4.3.1.13,8]undecane (TATU) and alkyl iodides, such as methyl, ethyl, propyl, butyl, pentyl and hexyl iodide (2a-f), in dry acetonitrile at room temperature.ResultsThe structures of these new quaternary ammonium salts were established using various spectral and electrospray ionization mass spectrometry (ESI-MS) analyses. Compound (3b) was also analyzed using X-ray crystallography.ConclusionIt was noted that alkyl chain length did not significantly affect the reaction because all employed alkyl iodide electrophiles reacted in a similar fashion with the aminal 1 to produce the corresponding mono N-quaternary ammonium salts, which were characterized by spectroscopic and analytical techniques.
Highlights
Novel mono N-alkyl quaternary ammonium salts (3a-f) were prepared using the Menschutkin reaction from the cage adamanzane type aminal 1,3,6,8-tetraazatricyclo[4.3.1.13,8]undecane (TATU) and alkyl iodides, such as methyl, ethyl, propyl, butyl, pentyl and hexyl iodide (2a-f), in dry acetonitrile at room temperature
Our results suggest that the anomeric effect evidenced by the shortening and lengthening of N-C-N bond lengths and distortion of the CN-C bond angles increases the p character of noncharged nitrogens and reduces the N-pyramidality, thereby making the nitrogen less nucleophilic [12]
These quaternary ammonium salts provide new evidence characterizing anomeric effects in aminals that possess one nitrogen atom with a full positive charge. These results demonstrated that the degree of nucleophilicity of the specific nitrogen atoms varies and increases with higher sp3 character
Summary
It was noted that alkyl chain length did not significantly affect the reaction because all employed alkyl iodide electrophiles reacted in a similar fashion with the aminal 1 to produce the corresponding mono Nquaternary ammonium salts, which were characterized by spectroscopic and analytical techniques
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