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

ABSTRACT: 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=C^dme] (20b) and to ?18 kcal·mol^-1 in cationic species like [Me₃O⁺-CH₃···OH₂]⁺ (8a).

SUBMITTER: Mooibroek TJ

PROVIDER: S-EPMC6767229 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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

Mooibroek Tiddo J TJ

Molecules (Basel, Switzerland) 20190916 18

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). ...[more]

PMID: 31527496

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