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Open AccessArticle

Intermolecular Non-Covalent Carbon-Bonding Interactions with Methyl Groups: A CSD, PDB and DFT Study

van ’t Hoff Institute for Molecular Sciences, Universiteit van Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands
Molecules 2019, 24(18), 3370; https://doi.org/10.3390/molecules24183370
Received: 28 July 2019 / Revised: 5 September 2019 / Accepted: 12 September 2019 / Published: 16 September 2019
(This article belongs to the Special Issue Tetrel Bonds)
A systematic evaluation of the CSD and the PDB in conjunction with DFT calculations reveal that non-covalent Carbon-bonding interactions with X–CH3 can be weakly directional in the solid state (P ≤ 1.5) when X = N or O. This is comparable to very weak CH hydrogen bonding interactions and is in line with the weak interaction energies calculated (≤ –1.5 kcal·mol−1) of typical charge neutral adducts such as [Me3N-CH3···OH2] (2a). The interaction energy is enhanced to ≤–5 kcal·mol−1 when X is more electron withdrawing such as in [O2N-CH3··O=Cdme] (20b) and to ≤18 kcal·mol−1 in cationic species like [Me3O+-CH3···OH2]+ (8a). View Full-Text
Keywords: intermolecular interactions; non-covalent interactions; carbon-bonding interactions; crystal structure database analysis; density functional theory intermolecular interactions; non-covalent interactions; carbon-bonding interactions; crystal structure database analysis; density functional theory
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MDPI and ACS Style

Mooibroek, T.J. Intermolecular Non-Covalent Carbon-Bonding Interactions with Methyl Groups: A CSD, PDB and DFT Study. Molecules 2019, 24, 3370.

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