On the importance of electron correlation effects for the pi-pi interactions in cyclophanes

Chemistry : a European Journal
Stefan Grimme

Abstract

Correlated ab initio quantum chemical methods based on second-order perturbation theory and density functional theory (DFT) together with large atomic orbital (AO) basis sets are used to calculate the structures of four cyclophanes with two aromatic rings and one sulphur-containing phane with one aromatic ring. The calculated geometrical data for [2.2]paracyclophane, cyclophane (superphane), 8,16-dimethyl[2.2]metacyclophane, 16-methyl[2.2]metaparacyclophane, and 2,6,15-trithia[3(4,10)][7]metacyclophane are compared to experimental data from X-ray crystal structure determinations. In all cases, very accurate theoretical predictions are obtained from the recently developed spin-component-scaled MP2 (SCS-MP2) method, in which the deviations are within the experimental accuracy and expected crystal-packing or vibrational effects. Especially the inter-ring distances, which are determined by a detailed balance between attractive van der Waals (dispersive) and repulsive (Pauli) contributions, are very sensitive to the level of theory employed. While standard MP2 theory in general overestimates the dispersive interactions (pi-pi correlations) between the two aromatic rings leading to too short distances (between 3 and 8 pm), the opposi...Continue Reading

Citations

May 17, 2014·The Journal of Chemical Physics·Éric BrémondClémence Corminboeuf
Jan 28, 2006·The Journal of Chemical Physics·Stefan Grimme
Mar 1, 2012·The Journal of Chemical Physics·H DodziukJ Waluk
Feb 5, 2009·The Journal of Chemical Physics·Martin KleinschmidtStefan Grimme
Sep 4, 2009·The Journal of Chemical Physics·J C Sancho-García, A J Pérez-Jiménez
Dec 3, 2008·The Journal of Chemical Physics·J Grant Hill, James A Platts
Mar 20, 2012·The Journal of Chemical Physics·Meilin BaiShimin Hou
Sep 18, 2007·Journal of Molecular Modeling·Marcel SwartF Matthias Bickelhaupt
Oct 10, 2006·Physical Chemistry Chemical Physics : PCCP·J Grant HillHans-Joachim Werner
Jan 16, 2016·The Journal of Physical Chemistry. a·Taye B DemissieHenning Hopf
Jun 13, 2015·The Journal of Organic Chemistry·Steven M Bachrach, Meghan W Tang
Oct 1, 2016·The Journal of Physical Chemistry. a·Irena Majerz, Teresa Dziembowska
Oct 22, 2016·Chemistry : a European Journal·Josef B G GluyasPaul J Low
Aug 13, 2015·Journal of Computational Chemistry·Martin KauppChristoph Lambert
May 12, 2015·Physical Chemistry Chemical Physics : PCCP·L-C WuY Wang
May 4, 2016·Physical Chemistry Chemical Physics : PCCP·Daniel H FrieseAntonio Rizzo
Mar 30, 2011·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Stefan GrimmeStephan Ehrlich
Feb 14, 2015·Chemistry : a European Journal·Hilke WolfDietmar Stalke
Sep 7, 2006·Journal of Computational Chemistry·Stefan Grimme
Aug 1, 2007·Physical Chemistry Chemical Physics : PCCP·Tobias Schwabe, Stefan Grimme
Mar 20, 2008·Angewandte Chemie·Stefan Grimme
Nov 1, 2008·Chemistry : a European Journal·Michael HagemannNorbert W Mitzel
May 6, 2009·Angewandte Chemie·Hans-Jörg Schneider
May 13, 2010·Physical Chemistry Chemical Physics : PCCP·Robert HuenerbeinStefan Grimme
Jul 1, 2010·Physical Chemistry Chemical Physics : PCCP·Christof SchonBernd Engels
Jul 14, 2005·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Manuel Piacenza, Stefan Grimme
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May 14, 2011·Physical Chemistry Chemical Physics : PCCP·Christof SchonBernd Engels
Jun 5, 2013·Chemical Communications : Chem Comm·Jérémy StemperAngela Marinetti

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