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Contents Vol 67(12)

Hydrogen Bonding of O-Ethylxanthate Compounds and Neutron Structural Determination of C–H···S Interactions

Lauren K. Macreadie A C , Alison J. Edwards B , Anthony S. R. Chesman C and David R. Turner A D
+ Author Affiliations
- Author Affiliations

A School of Chemistry, Monash University, Clayton, Vic. 3800, Australia.

B Bragg Institute, Australian Nuclear Science and Technology Organisation, Locked Bag 2001, Kirrawee DC, NSW 2234, Australia.

C CSIRO Manufacturing Flagship, Bayview Avenue, Clayton, Vic. 3168, Australia.

D Corresponding author. Email: david.turner@monash.edu

Australian Journal of Chemistry 67(12) 1829-1839 https://doi.org/10.1071/CH14355
Submitted: 4 June 2014  Accepted: 26 June 2014   Published: 10 October 2014

Abstract

A range of ethylxanthate (EtXn) salts, containing either protic or aprotic cations (guanidinium (1), methylammonium (2), dimethylammonium (3), trimethylammonium (4), tetramethylammonium (5), tetraethylammonium (6), and tetrapropylammonium (7)), have been synthesised and structurally characterised. The cations in these compounds differ in their degree of hydrogen-bonding ability, i.e. the number of donor groups, with significant structural consequences. Compounds 1–4 contain cations that are able to form N–H···S hydrogen bonds, with six, three, two, and one donor groups in 1–4 respectively. The number of donor atoms affects greatly the dimensionality of the hydrogen-bonding networks in the solid state. The structure of 1 has a 3-D hydrogen-bonding network, 2 and 3 form 2-D sheets and 1-D chains respectively, whereas the lone NH donor group in 4 has strong hydrogen bonding only within a discrete cation–anion pair. The tetraalkylammonium salts 5–7 have no strong hydrogen bonding, with only C–H···S and C–H···O interactions possible. To determine unambiguously the presence of such interactions, single-crystal Laue neutron diffraction data were obtained for compound 5, providing a fully anisotropic model, which can be used to rationalise potential close interactions in the other structures. The neutron structure of 5 confirms the existence of C–H···S hydrogen bonds, with the H···S distance falling well within the sum of the van der Waals radii of the atoms. The close-packing in 5–7 is mediated solely through these weak interactions, with the size of the cations influencing the structures.


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