1035454-35-3Relevant academic research and scientific papers
Through-space interactions between parallel-offset arenes at the van der Waals distance: 1,8-Diarylbiphenylene syntheses, structure and QM computations
Cozzi, Franco,Annunziata, Rita,Benaglia, Maurizio,Baldridge, Kim K.,Aguirre, Gerardo,Estrada, Jesus,Sritana-Anant, Yongsak,Siegel, Jay S.
, p. 2686 - 2694 (2008/09/20)
A model for studying polar-π interactions between arenes spaced at van der Waals distances is developed on the basis of peri-diarylbiphenylenes. A set of 1,8-diarylbiphenylenes is synthesized comprising two Hammett series, one with reference to mesityl ring interactions and the other with reference to pentafluorophenyl ring interactions. X-Ray crystal structures of several derivatives are determined. Barriers to rotation of the probe aryl ring are derived from dynamic NMR data and show a trend for the mesityl reference series (ΔG≠vs. σ°). The model is also used as a test for comparison of modern density functional methods, including B3LYP, M06-2X and BMK functionals; dispersive effects are seen to be an important factor in the proper theoretical treatment of arene interactions. the Owner Societies.
