Counterintuitive affinity of [2.2]paracyclophane to cations

David Quiñonero, Antonio Frontera, Carolina Garau, Pau Ballester, Antoni Costa, Pere M. Deyà, Fabio Pichierri

研究成果: Article査読

11 被引用数 (Scopus)

抄録

Geometries and binding energies of complexes of cations with benzene, [2.2]paracyclophane and a [2.2]paraheterocyclophane are computed and compared using ab initio calculations. [2.2]Paracyclophane is not used for building cation receptors because of its small cavity. Here, we demonstrate that its binding capability toward cations using one aromatic ring is superior to benzene in ∼10 kcal/mol. This unexpected difference is explained by the reduction, upon complexation, of the repulsive interaction of the π-systems, which is due to the close proximity of the two benzene rings. Experimental results derived from the analysis of X-ray structures retrieved from the CSD support this explanation.

本文言語English
ページ(範囲)59-64
ページ数6
ジャーナルChemical Physics Letters
408
1-3
DOI
出版ステータスPublished - 2005 6 7

ASJC Scopus subject areas

  • Physics and Astronomy(all)
  • Physical and Theoretical Chemistry

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