Experimental and theoretical charge density study of polymorphic isonicotinamide-oxalic acid molecular complexes with strong O...H...N hydrogen bonds

The Journal of Physical Chemistry. a
Marc SchmidtmannChick C Wilson

Abstract

Two polymorphs of the 2:1 molecular complex of isonicotinamide and oxalic acid have been characterized by combined X-ray charge density and single-crystal neutron diffraction studies at 100 K. Both polymorphs show strong O-H...N intermolecular hydrogen bonding between the acid and the pyridine base. As is typical of short, strong hydrogen bonds (SSHBs), the covalent O-H bonds are considerably elongated to 1.161(3) and 1.235(5) A, and the H...N interactions are correspondingly short at 1.398(3) and 1.313(6) A in Forms I and II, respectively. The neutron diffraction data indicate no pronounced H dynamics in the SSHBs, and in the case of Form II the SSHB can be described as quasicentered. In addition to the experimental charge densities, theoretical charge densities have been determined from ab initio calculations within the full periodic environment of the crystalline state. The SSHBs are found to be covalent in nature according to the topological analysis of the experimental and theoretical charge densities and application of the source function. Aside from the SSHBs, moderate N-H...O and weak C-H...O interactions are also present in the molecular complexes, for which hydrogen bond energies are estimated from energy densities an...Continue Reading

References

Oct 1, 1995·Acta Crystallographica. Section B, Structural Science·R H Blessing
Jun 15, 1992·Physical Review. B, Condensed Matter·J P Perdew, Y Wang
Apr 28, 2001·Acta Crystallographica. Section A, Foundations of Crystallography·A VolkovP Coppens
May 25, 2001·Acta Crystallographica. Section B, Structural Science·B L RodriguesN G Fernandes
Sep 29, 2001·Chemistry : a European Journal·J OvergaardB B Iversen
Dec 20, 2002·Angewandte Chemie·Thomas Steiner
Feb 21, 2003·Journal of Computational Chemistry·Carlo GattiLuca Bertini
Apr 3, 2003·Journal of the American Chemical Society·Paul R MallinsonKrzysztof Wozniak
Aug 21, 2003·Organic & Biomolecular Chemistry·David E HibbsRoss O Piltz
Oct 13, 2004·Acta Crystallographica. Section A, Foundations of Crystallography·Carlo Gatti, Luca Bertini
Jan 27, 2007·The Journal of Physical Chemistry. a·M V VenerV G Tsirelson
Mar 3, 2007·Faraday Discussions·Carlo Gatti, Davide Lasi
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Jul 3, 2008·The Journal of Physical Chemistry. a·Paula M B PiccoliDusan Hadzi
Jun 6, 2009·The Journal of Physical Chemistry. a·Milind M Deshmukh, Shridhar R Gadre

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Citations

Feb 2, 2016·Biomacromolecules·Volker L DeringerRichard Dronskowski
Dec 19, 2014·Chemistry Central Journal·Anna Krawczuk, Piero Macchi
Mar 2, 2019·Chemistry : a European Journal·Kasper TolborgBo B Iversen
Aug 19, 2014·Chemical Communications : Chem Comm·Volker L DeringerRichard Dronskowski
Oct 14, 2010·Accounts of Chemical Research·Charles L Perrin
Oct 23, 2010·The Journal of Physical Chemistry. a·J Seliger, V Žagar

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