| Abstract
| - A study of the crystal packing of six derivatives of N-benzyl-2-phenylpyridinium bromidedemonstrated the potential importance of synergism between π-stacking interactions and stericsubstituent effects in the determination of molecular orientations in an ionic lattice. N-Benzyl-2-phenylpyridinium bromide was substituted with 4-methoxybenzyl, 4-cyanobenzyl, 4-trifluoromethylbenzyl, 4-trifluoromethyl-2,3,5,6-tetrafluorobenzyl, and 2,3,4,5,6-pentafluorobenzyl. Nonangular para substituents on the benzyl ring gave rise to predictable changes in the solid state.These substituents anchored and aligned the molecules by complete or partial interdigitation. Theincreased stability of perfluoroarene/arene interactions vs arene/arene interactions were manifestin the presence of the strong ionic lattice. The fact that electronic perturbation in π-stacked orientedmolecules in these crystals demonstrated partial orthogonality between the directional forcesinvolved in the establishment of the ionic lattice and the much weaker directional contributions tothe lattice energy from π-stacking.
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