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The X–C⋯Y (X = O/F, Y = O/S/F/Cl/Br/N/P) ‘carbon bond’ and hydrophobic interactions
Abstract
While the tetrahedral face of methane has an electron rich centre and can act as a hydrogen bond acceptor, substitution of one of its hydrogens with some electron withdrawing group (such as -F/OH) can make the opposite face electron deficient. Electrostatic potential calculations confirm this and high level quantum calculations show interactions between the positive face of methanol/methyl fluoride and electron rich centers of other molecules such as H2O. Analysis of the wave functions of atoms in molecules shows the presence of an unusual C···Y interaction, which could be called 'carbon bonding'. NBO analysis and vibrational frequency shifts confirm the presence of this interaction. Given the properties of alkyl groups bonded to electronegative elements in biological molecules, such interactions could play a significant role, which is yet to be recognized. This and similar interactions could give an enthalpic contribution to what is called the 'hydrophobic interactions'.
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Definition of the halogen bond (IUPAC Recommendations 2013).
Desiraju, G. R., Ho, P. S., Kloo, L., Legon, A. C., Marquardt, R., Metrangolo, P., Politzer, P., Resnati, G., & Rissanen, K. (2013) · Pure and Applied Chemistry · doi:10.1351/pac-rec-12-05-10 · Cited by 1,957
Cited by
Hydrogen bonding in ionic liquids
Hunt, P. A., Ashworth, C. R., & Matthews, R. P. (2015) · Chemical Society Reviews · doi:10.1039/c4cs00278d · Cited by 836
The Bright Future of Unconventional σ/π‐Hole Interactions
Bauzá, A., Mooibroek, T. J., & Frontera, A. (2015) · ChemPhysChem · doi:10.1002/cphc.201500314 · Cited by 710
Anion Recognition Strategies Based on Combined Noncovalent Interactions
Molina, P., Zapata, F., & Caballero, A. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00814 · Cited by 406
Metadata
- Authors
- Mani, D., & Arunan, E.
- Venue
- Physical Chemistry Chemical Physics
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2013
- Volume
- 15
- Issue
- 34
- Pages
- 14377
- ISSN
- 1463-9076 (ISSN-L)
- 1463-9084
- OpenAlex
- W2071069485
- Cited by
- 339
- References
- 1
- FWCI
- 24.16
- Type
- journal article
- Language
- en
- Open access
- closed
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- Mani, D., & Arunan, E. (2013). The X–C⋯Y (X = O/F, Y = O/S/F/Cl/Br/N/P) ‘carbon bond’ and hydrophobic interactions. Physical Chemistry Chemical Physics. https://doi.org/10.1039/c3cp51658j
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