Steric Crowding in Tetrel Bonds

The Journal of Physical Chemistry. a
Steve Scheiner

Abstract

The tetravalent character of tetrel atoms leaves only limited room for an incoming nucleophile to approach and engage in a noncovalent bond with a tetrel atom. Any such approach can only occur at the expense of internal geometric distortions. The balance between attractive forces and repulsive steric crowding was studied for a series of Lewis acids of the type FTR3(T = Si, Ge, Sn, Pb) which were allowed to interact with various bases. The strength and other properties of the tetrel bond are examined as the R groups are made progressively larger, varying from H and CH3to isopropyl and tert-butyl, which induce steric crowding with the incoming base. The effects of crowding which impede the bond can be offset by enlarging the T atom, by adding electron-withdrawing substituents to the Lewis acid, or by considering stronger bases such as anions. The tetrel bond energies reach up to 10 kcal/mol for a pair of neutral molecules with no electron-withdrawing substituents on the Lewis acid. Adding -CF3substituents grows the interaction energy to as high as 35 kcal/mol, and a further increment occurs for an anionic base, taking the maximum up to 54 kcal/mol.

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Citations

May 16, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sławomir J Grabowski
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Jul 27, 2021·The Journal of Physical Chemistry. a·Steve Scheiner
Sep 11, 2018·The Journal of Physical Chemistry. a·Steve Scheiner
Dec 23, 2020·The Journal of Physical Chemistry. a·Steve Scheiner
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Dec 4, 2021·Journal of Computational Chemistry·Steve Scheiner

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