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Issue 31, 2011
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Weak H-bonds. Comparisons of CH⋯O to NH⋯O in proteins and PH⋯N to direct P⋯N interactions

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Abstract

Whereas CH⋯O H-bonds are usually weaker than interpeptide NH⋯O H-bonds, this is not necessarily the case within proteins. The nominally weaker CH⋯O are surprisingly strong, comparable to, and in some cases stronger than, the NH⋯O H-bonds in the context of the forces that hold together the adjacent strands in protein β-sheets. The peptide NH is greatly weakened as proton donor in certain conformations of the protein backbone, particularly extended structures, and forms correspondingly weaker H-bonds. The PH group is a weak proton donor, but will form PH⋯N H-bonds. However, there is a stronger interaction in which P can engage, in which the P atom, not the H, directly approaches the N electron donor to establish a direct P⋯N interaction. This approach is stabilized by the same sort of electron transfer from the N lone pair to the P–H σ* antibond that characterizes the PH⋯N H-bond.

Graphical abstract: Weak H-bonds. Comparisons of CH⋯O to NH⋯O in proteins and PH⋯N to direct P⋯N interactions

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Publication details

The article was received on 17 Feb 2011, accepted on 21 Apr 2011 and first published on 13 May 2011


Article type: Perspective
DOI: 10.1039/C1CP20427K
Citation: Phys. Chem. Chem. Phys., 2011,13, 13860-13872
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    Weak H-bonds. Comparisons of CH⋯O to NH⋯O in proteins and PH⋯N to direct P⋯N interactions

    S. Scheiner, Phys. Chem. Chem. Phys., 2011, 13, 13860
    DOI: 10.1039/C1CP20427K

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