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Crystals 2016, 6(3), 26;

RCH3···O Interactions in Biological Systems: Are They Trifurcated H-Bonds or Noncovalent Carbon Bonds?

Department of Chemistry, Universitat de les Illes Balears, Crta de Valldemossa km 7.5, 07122 Palma de Mallorca (Baleares), Spain
Author to whom correspondence should be addressed.
Academic Editor: Sławomir J. Grabowski
Received: 26 January 2016 / Revised: 9 March 2016 / Accepted: 14 March 2016 / Published: 17 March 2016
(This article belongs to the Special Issue Analysis of Hydrogen Bonds in Crystals)
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In this manuscript, we combine high-level ab initio calculations on some model systems (XCH3 σ-hole/H-bond donors) and a Protein Data Bank (PDB) survey to distinguish between trifurcated H-bonds and noncovalent carbon bonds in XCH3···O complexes (X = any atom or group). Recently, it has been demonstrated both experimentally and theoretically the importance of noncovalent carbon bonds in the solid state. When an electron-rich atom interacts with a methyl group, the role of the methyl group is commonly viewed as a weak H-bond donor. However, if the electron-rich atom is located equidistant from the three H atoms, the directionality of each individual H-bond in the trifurcated binding mode is poor. Therefore, the XCH3···O interaction could be also defined as a tetrel bond (C···O interaction). In this manuscript, we shed light into this matter and demonstrate the importance of XCH3···O noncovalent carbon bonding interactions in two relevant protein-substrate complexes retrieved from the PDB. View Full-Text
Keywords: H-bonding; tetrel bonding; PDB search; ab initio calculations H-bonding; tetrel bonding; PDB search; ab initio calculations

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Bauzá, A.; Frontera, A. RCH3···O Interactions in Biological Systems: Are They Trifurcated H-Bonds or Noncovalent Carbon Bonds? Crystals 2016, 6, 26.

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