Steric "attraction": not by dispersion alone

Beilstein Journal of Organic Chemistry
Ganna Gryn'ova, Clemence Corminboeuf

Abstract

Non-covalent interactions between neutral, sterically hindered organic molecules generally involve a strong stabilizing contribution from dispersion forces that in many systems turns the 'steric repulsion' into a 'steric attraction'. In addition to London dispersion, such systems benefit from electrostatic stabilization, which arises from a short-range effect of charge penetration and gets bigger with increasing steric bulk. In the present work, we quantify this contribution for a diverse set of molecular cores, ranging from unsubstituted benzene and cyclohexane to their derivatives carrying tert-butyl, phenyl, cyclohexyl and adamantyl substituents. While the importance of electrostatic interactions in the dimers of sp2-rich (e.g., π-conjugated) cores is well appreciated, less polarizable assemblies of sp3-rich systems with multiple short-range CH···HC contacts between the bulky cyclohexyl and adamantyl moieties are also significantly influenced by electrostatics. Charge penetration is drastically larger in absolute terms for the sp2-rich cores, but still has a non-negligible effect on the sp3-rich dimers, investigated herein, both in terms of their energetics and equilibrium interaction distances. These results emphasize the i...Continue Reading

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Citations

Jan 28, 2021·The Journal of Physical Chemistry. a·John M Herbert, Kevin Carter-Fenk
Jun 8, 2021·Chemical Science·Kevin Carter-Fenk, John M Herbert
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Oct 26, 2018·Journal of Chemical Theory and Computation·Sławomir A BojarowskiPaulina M Dominiak

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