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Issue 34, 2013
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The X–C⋯Y (X = O/F, Y = O/S/F/Cl/Br/N/P) ‘carbon bond’ and hydrophobic interactions

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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’.

Graphical abstract: The X–C⋯Y (X = O/F, Y = O/S/F/Cl/Br/N/P) ‘carbon bond’ and hydrophobic interactions

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Publication details

The article was received on 18 Apr 2013, accepted on 12 Jun 2013 and first published on 12 Jun 2013


Article type: Paper
DOI: 10.1039/C3CP51658J
Citation: Phys. Chem. Chem. Phys., 2013,15, 14377-14383

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    The X–C⋯Y (X = O/F, Y = O/S/F/Cl/Br/N/P) ‘carbon bond’ and hydrophobic interactions

    D. Mani and E. Arunan, Phys. Chem. Chem. Phys., 2013, 15, 14377
    DOI: 10.1039/C3CP51658J

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