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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; in revised form: 9 February 2012 / Accepted: 15 February 2012 / Published: 21 February 2012
Abstract: 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
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Mori, Y.; Yamada, S. Contribution of Cation-π Interactions in Iminium Catalysis. Molecules 2012, 17, 2161-2168.
Mori Y, Yamada S. Contribution of Cation-π Interactions in Iminium Catalysis. Molecules. 2012; 17(2):2161-2168.
Mori, Yukie; Yamada, Shinji. 2012. "Contribution of Cation-π Interactions in Iminium Catalysis." Molecules 17, no. 2: 2161-2168.