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Hydrogen Bonding in the Water Stabilized Structure of the Modified Unsymmetrically Substituted Viologen Chromophore, N-ethyl-N′-(2-phosphonoethyl)-4,4′-bipyridylium Dichloride

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Abstract

The crystal structure of the modified unsymmetrically N,N′-substituted viologen chromophore, N-ethyl-N′-(2-phosphonoethyl)-4,4′-bipyridinium dichloride 0.75 hydrate (1) has been determined. Crystals are triclinic, space group P−1 with Z = 2 in a cell with a = 7.2550(1), b = 13.2038(5), c = 18.5752(7) Å, α = 86.495(3), β = 83.527(2), γ = 88.921(2)°. The two independent but pseudo-symmetrically related cations in the asymmetric unit form one-dimensional hydrogen-bonded chains through short homomeric phosphonic acid O–H···O links [2.455(4), 2.464(4) Å] while two of the chloride anions are similarly strongly linked to phosphonic acid groups [O–H···Cl, 2.889(4), 2.896(4) Å]. The other two chloride anions together with the two water molecules of solvation (one with partial occupancy) form unusual cyclic hydrogen-bonded bis(Cl···water) dianion units which lie between the layers of bipyridylium rings of the cation chain structures with which they are weakly associated.

Graphical Abstract

The crystal structure determination of unsymmetrically substituted viologen N-ethyl-N′-(2-phosphonoethyl)-4,4′-bipyridylium dichloride 0.75 hydrate shows the presence of strong intermolecular phosphonate O–H···O and O–H···Cl interactions together with unusual cyclic hydrogen-bonded bis(chloride···water) dianion units giving one-dimensional chain structures.

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Acknowledgments

The authors acknowledge financial support from the Australian Research Council, the School of Physical and Chemical Sciences (Queensland University of Technology) and the Commonwealth Scientific and Industrial Research Organisation.

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Authors and Affiliations

  1. School of Physical and Chemical Sciences, Queensland University of Technology, G.P.O. Box 2434, Brisbane, QLD, 4001, Australia

    Graham Smith & Geoffrey D. Will

  2. Energy Technology, CSIRO, Newcastle Energy Centre, Mayfield West, NSW, 2304, Australia

    Gregory J. Wilson

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  1. Graham Smith
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  2. Geoffrey D. Will
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Correspondence to Graham Smith.

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Smith, G., Will, G.D. & Wilson, G.J. Hydrogen Bonding in the Water Stabilized Structure of the Modified Unsymmetrically Substituted Viologen Chromophore, N-ethyl-N′-(2-phosphonoethyl)-4,4′-bipyridylium Dichloride. J Chem Crystallogr 40, 248–252 (2010). https://doi.org/10.1007/s10870-009-9642-9

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