Through-space interactions between face-to-face, center-to-edge oriented arenes: importance of polar–π effects

文献情報

出版日 2002-12-06

DOI 10.1039/B208871A

インパクトファクター 3.876

著者

Franco Cozzi, Rita Annunziata, Maurizio Benaglia, Mauro Cinquini, Laura Raimondi, Kim K. Baldridge, Jay S. Siegel

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要旨

Two series of conformationally restricted polycyclic compounds (1–3 and 4–7) have been synthesized as model systems for studying the through-space interactions between face-to-face, center-to-edge (parallel-offset) oriented arenes. These compounds feature different X substituents on one of the interacting rings. By monitoring the variation of the ΔG≠ for the rotation around the aryl–aryl bond in 1–7 as a function of X by 2D [1H,1H] EXSY NMR spectroscopy, it was found that the barriers increase on passing from electron-donating to electron-withdrawing substituted derivatives. Quantum mechanical calculations [MP2/DVZ (2d,p)//B3LYP/DVZ(2d,p)] gave barrier values and variations in agreement with the experimental data. The results are consistent with a repulsive arene–arene interaction dominated by electrostatic effects.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Through-space interactions between face-to-face, center-to-edge oriented arenes: importance of polar–π effects

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