Intermolecular Non-Covalent Carbon-Bonding Interactions with Methyl Groups: A CSD, PDB and DFT Study
A systematic evaluation of the CSD and the PDB in conjunction with DFT calculations reveal that non-covalent Carbon-bonding interactions with X−CH<sub>3</sub> can be weakly directional in the solid state (<i>P</i> ≤ 1.5) when X = N or O. This is comparable...
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| Format: | Article |
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MDPI AG
2019-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/18/3370 |
| _version_ | 1818020421184782336 |
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| author | Tiddo J. Mooibroek |
| author_facet | Tiddo J. Mooibroek |
| author_sort | Tiddo J. Mooibroek |
| collection | DOAJ |
| description | A systematic evaluation of the CSD and the PDB in conjunction with DFT calculations reveal that non-covalent Carbon-bonding interactions with X−CH<sub>3</sub> can be weakly directional in the solid state (<i>P</i> ≤ 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<sup>−1</sup>) of typical charge neutral adducts such as [Me<sub>3</sub>N-CH<sub>3</sub>···OH<sub>2</sub>] (<b>2a</b>). The interaction energy is enhanced to ≤−5 kcal·mol<sup>−1</sup> when X is more electron withdrawing such as in [O<sub>2</sub>N-CH<sub>3</sub>··O=C<sup>dme</sup>] (<b>20b</b>) and to ≤18 kcal·mol<sup>−1</sup> in cationic species like [Me<sub>3</sub>O<sup>+</sup>-CH<sub>3</sub>···OH<sub>2</sub>]<sup>+</sup> (<b>8a</b>). |
| first_indexed | 2024-04-14T08:05:48Z |
| format | Article |
| id | doaj.art-0a1545f8c2d74aeaba847683c80200db |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-14T08:05:48Z |
| publishDate | 2019-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-0a1545f8c2d74aeaba847683c80200db2022-12-22T02:04:45ZengMDPI AGMolecules1420-30492019-09-012418337010.3390/molecules24183370molecules24183370Intermolecular Non-Covalent Carbon-Bonding Interactions with Methyl Groups: A CSD, PDB and DFT StudyTiddo J. Mooibroek0van ’t Hoff Institute for Molecular Sciences, Universiteit van Amsterdam, Science Park 904, 1098 XH, Amsterdam, The NetherlandsA systematic evaluation of the CSD and the PDB in conjunction with DFT calculations reveal that non-covalent Carbon-bonding interactions with X−CH<sub>3</sub> can be weakly directional in the solid state (<i>P</i> ≤ 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<sup>−1</sup>) of typical charge neutral adducts such as [Me<sub>3</sub>N-CH<sub>3</sub>···OH<sub>2</sub>] (<b>2a</b>). The interaction energy is enhanced to ≤−5 kcal·mol<sup>−1</sup> when X is more electron withdrawing such as in [O<sub>2</sub>N-CH<sub>3</sub>··O=C<sup>dme</sup>] (<b>20b</b>) and to ≤18 kcal·mol<sup>−1</sup> in cationic species like [Me<sub>3</sub>O<sup>+</sup>-CH<sub>3</sub>···OH<sub>2</sub>]<sup>+</sup> (<b>8a</b>).https://www.mdpi.com/1420-3049/24/18/3370intermolecular interactionsnon-covalent interactionscarbon-bonding interactionscrystal structure database analysisdensity functional theory |
| spellingShingle | Tiddo J. Mooibroek Intermolecular Non-Covalent Carbon-Bonding Interactions with Methyl Groups: A CSD, PDB and DFT Study Molecules intermolecular interactions non-covalent interactions carbon-bonding interactions crystal structure database analysis density functional theory |
| title | Intermolecular Non-Covalent Carbon-Bonding Interactions with Methyl Groups: A CSD, PDB and DFT Study |
| title_full | Intermolecular Non-Covalent Carbon-Bonding Interactions with Methyl Groups: A CSD, PDB and DFT Study |
| title_fullStr | Intermolecular Non-Covalent Carbon-Bonding Interactions with Methyl Groups: A CSD, PDB and DFT Study |
| title_full_unstemmed | Intermolecular Non-Covalent Carbon-Bonding Interactions with Methyl Groups: A CSD, PDB and DFT Study |
| title_short | Intermolecular Non-Covalent Carbon-Bonding Interactions with Methyl Groups: A CSD, PDB and DFT Study |
| title_sort | intermolecular non covalent carbon bonding interactions with methyl groups a csd pdb and dft study |
| topic | intermolecular interactions non-covalent interactions carbon-bonding interactions crystal structure database analysis density functional theory |
| url | https://www.mdpi.com/1420-3049/24/18/3370 |
| work_keys_str_mv | AT tiddojmooibroek intermolecularnoncovalentcarbonbondinginteractionswithmethylgroupsacsdpdbanddftstudy |