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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Fluorinated methyl cation (CF(3)(+), CFH(2)(+))-alkyl nitrile cluster ions
J Alvarez1, J W Denault, R G Graham Cooks
1Department of Chemistry, Purdue University, West Lafayette, Indiana 47906-1393, USA.
Abstract:
Ion-molecule reactions of CF(3)(+) or CFH(2)(+) with an acetonitrile-butyronitrile mixture yield product cluster ions in which the two neutral molecules are associated with the cation. The structures of the ion-molecule product ions were investigated by collision-induced dissociation in a multi-quadrupole mass spectrometer. The cluster ions fragment by loss of one neutral alkyl nitrile. The abundance of the fragment ions shows an unexpected inverse correlation with the proton affinity of the alkyl nitrile. This result is inconsistent with the formation of a simple cation-bound dimeric cluster containing two alkyl nitrile molecules and a fluorinated methyl cation; instead, a pair of non-symmetrical dimeric complexes, separated by a large internal barrier, is indicated. This result is analogous to that observed for the putative methyl cation-bound heterodimer of acetonitrile and butyronitrile. Collision energy dependence studies and ab initio calculations suggest that the dimeric complexes are formed in potential energy wells located in an approximately symmetrical potential energy surface. Quasi-equilibrium theory calculations were used in order to obtain additional insights into the experimental data.
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