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Crystals 2017, 7(9), 261; doi:10.3390/cryst7090261

Electrostatic Potential and a Simple Extended Electric Dipole Model of Hydrogen Fluoride as Probes of Non-Bonding Electron Pairs in the Cyclic Ethers 2,5-Dihydrofuran, Oxetane and Oxirane

1
Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK
2
School of Chemistry, University of Bristol, Cantocks Close, Bristol BS8 1TS, UK
*
Author to whom correspondence should be addressed.
Academic Editors: Peter Politzer and Jane S. Murray
Received: 7 July 2017 / Revised: 16 August 2017 / Accepted: 22 August 2017 / Published: 25 August 2017
(This article belongs to the Special Issue Analysis of Halogen and Other σ-Hole Bonds in Crystals)
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Abstract

The electrostatic potential near to the oxygen atom in each of the cyclic ethers 2,5-dihydrofuran, oxetane and oxirane has been calculated by using a distributed multipole analysis (DMA) of each molecule. The electrostatic potential energy V(φ) of a unit non-perturbing positive charge was calculated (via the DMA of the cyclic ether molecule) as a function of the angle φ between the C2 axis of the cyclic ether and a vector of length r from the O atom to the unit charge. The resulting potential energy functions each has two equivalent minima. The angles φmin at the minima are compared with the angles φ0 and φe made by the O⋯H bond with the C2 axes in the cyclic ether⋯HF complexes, as determined by rotational spectroscopy and ab initio calculations at the CCSD(T)-F12c/cc-pVTZ-F12 level of theory, respectively. An electrostatic model of cyclic ether⋯HF complexes in which the DMA of the cyclic ether interacts with a simple extended electric dipole representation of HF is also used to calculate the variation of the potential energy VHF(φ) of the HF molecule with φ. The angles φmin generated by this model are also compared with φ0 and φe. The extent to which the electrostatic potential and the extended electric dipole HF model can be used as probes for the directions of non-bonding electron pairs carried by O in these cyclic ethers is discussed. View Full-Text
Keywords: hydrogen bond; noncovalent interactions; electrostatic potentials; distributed multipole analysis; nonbonding-pairs hydrogen bond; noncovalent interactions; electrostatic potentials; distributed multipole analysis; nonbonding-pairs
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Hill, J.G.; Legon, A.C. Electrostatic Potential and a Simple Extended Electric Dipole Model of Hydrogen Fluoride as Probes of Non-Bonding Electron Pairs in the Cyclic Ethers 2,5-Dihydrofuran, Oxetane and Oxirane. Crystals 2017, 7, 261.

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