Abstract
The interaction of 18-crown-6 (18C6), diaza-18-crown-6 (DA18C6), and dithia-18-crown-6 (DT18C6) with acetonitrile and malononitrile was investigated using infrared spectroscopy, 1 H and 13 C NMR spectroscopy, and molecular modeling. The interaction between 18C6 and the nitriles involves hydrogen bonding between the CH 3/CH 2 protons of the nitriles and the ether oxygens of the crown. In contrast, the interaction between the organic nitriles and DA18C6 involves the nitrogen of the nitrile group and the NH groups of the crown. Due to the bulkiness of the sulfur atoms of DT18C6, no interaction was observed to occur between acetonitrile and the crown.
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