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Molecules 2012, 17(2), 2161-2168; doi:10.3390/molecules17022161

Contribution of Cation-π Interactions in Iminium Catalysis

Department of Chemistry, Ochanomizu University, Otsuka, Bunkyo-ku, Tokyo, 112-8610, Japan
* Author to whom correspondence should be addressed.
Received: 12 January 2012 / Revised: 9 February 2012 / Accepted: 15 February 2012 / Published: 21 February 2012
(This article belongs to the Special Issue Organocatalysis)
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Ab initio calculations were carried out for a benzyl-substituted iminium cation derived from (E)-crotonaldehyde and a chiral imidazolidinone that was developed as an organocatalyst by MacMillan et al. At the MP2 level of theory it is predicted that the phenyl group is close to the iminium moiety in the most stable conformer, suggesting that the cation-π interaction contributes to the stabilization of this conformer. Energy decomposition analyses on model systems indicate that the electrostatic and polarization terms make significant contribution to the attractive interactions between the benzene ring and the iminium cation.
Keywords: cation-π interaction; iminium-π interaction; iminium cation; imidazolidinone organocatalyst; ab initio calculation cation-π interaction; iminium-π interaction; iminium cation; imidazolidinone organocatalyst; ab initio calculation
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Mori, Y.; Yamada, S. Contribution of Cation-π Interactions in Iminium Catalysis. Molecules 2012, 17, 2161-2168.

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