NDLI: DFT investigation on hydrogen bonding in cyclohexane-1,2,3,4,5-pentol crystal structure

Content Provider	Springer Nature Link
Author	Belanzoni, P. Carvalho, P. S. Theodoro, J. E. Thiemann, O. H. Ellena, J. Napolita, H. B.
Copyright Year	2014
Abstract	The cyclohexane-1,2,3,4,5-pentol,C$_{6}$H$_{12}$O$_{5}$ is a natural product extracted from Adiscanthus fusciflorus (Rutaceae). It crystallizes in the non-centrosymmetric space group P2$_{1}$ with one molecule in the asymmetric unit and it has been postulated to have at least ten strong O-H…O intermolecular interactions, two per each OH group of one molecule, producing a three-dimensional network. The crystal packing is defined by O-H…O hydrogen bonds. Due to the crucial role of the hydrogen bonds in defining the crystal structure, theoretical investigations in the gas phase have been carried out in order to explore the hydrogenbonding mechanism through a quantitative Kohn-Sham molecular orbital and corresponding energy decomposition analyses. The existence of a covalent component in hydrogen bonds has been proved which originates from donor-acceptor orbital interactions in the σ-electron system. Our analyses show that the stability of the crystal structure is enhanced by the formation of two hydrogen bonds with two vicinal molecules for each OH group in C$_{6}$H$_{12}$O$_{5}$ molecule with respect to the formation of one or two hydrogen bonds with only one vicinal molecule, thus confirming the proposed existence of ten strong O-H…O intermolecular interactions for each molecule in the asymmetric unit. The presence of a cooperativity effect is observed which originates from a charge separation induced by the two vicinal molecules hydrogenbonded to an OH group in C$_{6}$H$_{12}$O$_{5}$ molecule.
Starting Page	1596
Ending Page	1606
Page Count	11
File Format	PDF
ISSN	00224766
Journal	Journal of Structural Chemistry
Volume Number	55
Issue Number	8
e-ISSN	15738779
Language	English
Publisher	Pleiades Publishing
Publisher Date	2015-01-28
Publisher Place	Moscow
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	cyclitol X-ray diffraction DFT Inorganic Chemistry Physical Chemistry Atomic, Molecular, Optical and Plasma Physics Atomic/Molecular Structure and Spectra Solid State Physics
Content Type	Text
Resource Type	Article
Subject	Materials Chemistry Physical and Theoretical Chemistry Inorganic Chemistry

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