Spectroscopic studies of the interaction between crown ethers and organic nitriles.

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 NH 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.