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Issue 13, 2012
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Chemistry of density: extension and structural origin of Carnelley's rule in chloroethanes

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Abstract

Low-density liquids and solids, with all intermolecular contacts longer than the sum of van der Waals radii, are formed by all ethanes chlorinated at one locant: CH2ClCH3, CHCl2CH3 and CCl3CH3. The concepts of molecular symmetry described by Carnelley and that of point groups have been compared. Carnelley's rule, when applied to liquid and solid chloroethanes clearly reveals the density dependence on the presence of intermolecular Cl⋯Cl and H⋯Cl short contacts, or their absence due to steric hindrances of overcrowded substituents. At 2.62 GPa, CH2ClCH3 freezes directly into phase II, with molecules arranged into layers with short Cl⋯Cl, H⋯Cl and H⋯H contacts. Only for CH2ClCH3, both the low-density phase at low temperature and closely-packed phase above 2.62 GPa have been observed.

Graphical abstract: Chemistry of density: extension and structural origin of Carnelley's rule in chloroethanes

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Publication details

The article was received on 19 Jan 2012, accepted on 05 Apr 2012 and first published on 11 Apr 2012


Article type: Paper
DOI: 10.1039/C2CE25097G
Citation: CrystEngComm, 2012,14, 4496-4500
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    Chemistry of density: extension and structural origin of Carnelley's rule in chloroethanes

    M. Podsiadło, M. Bujak and A. Katrusiak, CrystEngComm, 2012, 14, 4496
    DOI: 10.1039/C2CE25097G

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