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Charge-density analysis using multipolar atom and spherical charge models: 2-methyl-1,3-cyclopentanedione, a compound displaying a resonance-assisted hydrogen bond

Abstract : The experimental charge-density distribution in 2-methyl-1,3-cyclopentanedione in the crystal state was analyzed by synchrotron X-ray diffraction data collection at 0.33 angstrom resolution. The molecule in the crystal is in the enol form. The experimental electron density was refined using the Hansen-Coppens multipolar model and an alternative modeling, based on spherical atoms and additional charges on the covalent bonds and electron lone-pair sites. The crystallographic refinements, charge-density distributions, molecular electrostatic potentials, dipole moments and intermolecular interaction energies obtained from the different charge-density models were compared. The experimental results are also compared with the theoretical charge densities using theoretical structure factors obtained from periodic quantum calculations at the B3LYP/6-31G** level. A strong intermolecular O-H center dot center dot center dot O hydrogen bond connects molecules along the [001] direction. The deformation density maps show the resonance within the O=C-C=C-OH fragment and merged lone pair lobes on the hydroxyl O atom. This resonance is further confirmed by the analysis of charges and topology of the electron density.
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https://hal.univ-lorraine.fr/hal-01521331
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Submitted on : Thursday, May 11, 2017 - 4:34:18 PM
Last modification on : Thursday, February 25, 2021 - 10:00:02 AM

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Ayoub Nassour, Maciej Kubicki, Jonathan Wright, Teresa Borowiak, Grzegorz Dutkiewicz, et al.. Charge-density analysis using multipolar atom and spherical charge models: 2-methyl-1,3-cyclopentanedione, a compound displaying a resonance-assisted hydrogen bond. Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, International Union of Crystallography, 2014, 70 (2), pp.197-211. ⟨10.1107/S2052520613031375⟩. ⟨hal-01521331⟩

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