Electron and Nuclear Positions in the Short Hydrogen Bond in Urotropine-N-oxide·Formic Acid

The crystal structure of urotropine-N-oxide·formic acid, as determined from multiple temperature single-crystal X-ray diffraction experiments in the range 123−295 K and from neutron diffraction at 123 K, is reported. There is a strong hydrogen bonding interaction between the OH of formic acid and th...

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Published in:The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Molecules, spectroscopy, kinetics, environment, & general theory, 2005-03, Vol.109 (9), p.1911-1919
Main Authors: Nygren, Cara L, Wilson, Chick C, Turner, John F. C
Format: Article
Language:English
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Summary:The crystal structure of urotropine-N-oxide·formic acid, as determined from multiple temperature single-crystal X-ray diffraction experiments in the range 123−295 K and from neutron diffraction at 123 K, is reported. There is a strong hydrogen bonding interaction between the OH of formic acid and the N-oxide of urotropine, with the oxygen−oxygen distance ranging from 2.4300(10) to 2.4469(10) Å. The electron density of the hydrogen atom associated with this interaction was located in the Fourier difference maps of the spherical atom refinement after all heavy atom positions were determined. The maximum of the electron density associated with the hydrogen bond is located approximately 1.16 Å from the formate segment, though the distribution of electron density is very broad. The electron density associated with the H atom is thus shown by these accurate X-ray diffraction experiments to be approximately centered at all temperatures studied. This was conclusively confirmed by single-crystal neutron diffraction data obtained at 123 K, from which statistically equivalent O−H distances of 1.221(7) and 1.211(7) Å were obtained.
ISSN:1089-5639
1520-5215
DOI:10.1021/jp047187r