Molecular Balances Based on Aliphatic CH−π and Lone-Pair−π Interactions

CH···π and lone-pair···π interactions are estimated for a series of conformationally dynamic bicyclic N-aryliimides. On the basis of their strengths and mutual synergy/competition, the molecules prefer a folded/unfolded conformation. Calculations suggest strategies to selectively isolate the folded...

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Bibliographic Details
Published in:The journal of physical chemistry letters 2012-06, Vol.3 (11), p.1493-1496
Main Authors: Nijamudheen, A, Jose, Deepthi, Shine, A, Datta, Ayan
Format: Article
Language:English
Subjects:
Energy Conversion and Storage
Energy and Charge Transport
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Summary:CH···π and lone-pair···π interactions are estimated for a series of conformationally dynamic bicyclic N-aryliimides. On the basis of their strengths and mutual synergy/competition, the molecules prefer a folded/unfolded conformation. Calculations suggest strategies to selectively isolate the folded form by increasing the strength of the attractive CH···π interaction or removing the lone-pair···π repulsion. While the barrier for the folded ⇄ unfolded transformation is too large to conformationally lock the molecules in either of the conformers, the dynamics for hopping of the alkyl group across rings and tumbling over the rings are found to be facile in the folded conformation.
ISSN:1948-7185
1948-7185
DOI:10.1021/jz300473v