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One-dimensional hydrogen-bonded structures in the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with 8-hydroxyquinoline, 8-aminoquinoline and quinoline-2-carboxylic acid (quinaldic acid)

Smith, Graham, Wermuth, Urs D., & White, Jonathan M. (2008) One-dimensional hydrogen-bonded structures in the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with 8-hydroxyquinoline, 8-aminoquinoline and quinoline-2-carboxylic acid (quinaldic acid). Acta Crystallographica. Section C: Crystal Structure Communications, C64(3), o180-o183.

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Abstract

The structures of the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with 8-hydroxyquinoline, 8-aminoqunoline and with quinoline-2-carboxylic acid (quinaldic acid), namely anhydrous 8-hydroxyquinolinium 2-carboxy-4,5-dichlorobenzoate C~9~H~8~NO^+^ ^.^ C~8~H~3~Cl~2~O~4~^-^ (I) and 8-aminoquinolinium 2-carboxy-4,5-dichlorobenzoate C~9~H~9~N~2~^+^ ^.^ C~8~H~3~Cl~2~O~4~^-^ (II), and the adduct hydrate 2-carboxyquinolinium 2-carboxy-4,5- dichlorobenzoate quinolinium-2-carboxylate monohydrate C~10~H~8~NO~2~^+^ ^.^ C~8~H~3~Cl~2~O~4~^-^ ^.^ C~10~H~7~NO~2~ ^.^ H~2~O (III) have been determined at 130 K. Compounds (I) and (II) are isomorphous and all compounds have one-dimensional hydrogen-bonded chain structures, in (I) through O-H...O~carboxyl~ extensions and in (II) through N^+^-H...O~carboxyl~ extensions of cation--anion pairs. In (III), a hydrogen-bonded cyclic R^2^~2~(10) pseudo-dimer unit comprising a protonated quinaldic acid cation and a zwitterionic quinaldic acid adduct molecule is found and is propagated through a carboxylic acid O-H...O~carboxyl~ and water O-H...O~carboxyl~ interactions. In both (I) and (II) there are also cation-anion aromatic ring pi-pi associations. This work further illustrates the utility of both hydrogen phthalate anions and the interactive-group-substituted quinoline cations in formation of low-dimensional hydrogen-bonded structures.

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ID Code: 12960
Item Type: Journal Article
Keywords: proton, transfer compounds, hydrogen bonding, crystal structure
DOI: 10.1107/S0108270108004034
ISSN: 0108-2701
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > PHYSICAL CHEMISTRY (INCL. STRUCTURAL) (030600) > Structural Chemistry and Spectroscopy (030606)
Divisions: Past > QUT Faculties & Divisions > Faculty of Science and Technology
Copyright Owner: Copyright 2008 IUCr
Copyright Statement: Reproduced in accordance with the copyright policy of the publisher.
Deposited On: 11 Mar 2008
Last Modified: 29 Feb 2012 23:51

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