Zero-, one- and two-dimensional hydrogen-bonded structures in the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with the monocyclic heteroaromatic Lewis bases 2-aminopyrimidine, nicotinamide and isonicotinamide

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Title Zero-, one- and two-dimensional hydrogen-bonded structures in the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with the monocyclic heteroaromatic Lewis bases 2-aminopyrimidine, nicotinamide and isonicotinamide
Author Smith, Graham; Wermuth, Urs; White, Jonathan M.
Journal Name Acta Crystallographica. Section C: Crystal Structure Communications
Year Published 2009
Place of publication United States
Publisher Wiley-Blackwell Publishing, Inc.
Abstract The structures of the anhydrous 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid (DCPA) with the monocyclic heteroaromatic Lewis bases 2-aminopyrimidine, 3-(aminocarbonyl)pyridine (nicotinamide) and 4-(aminocarbonyl)pyridine (isonicotinamide), namely 2-aminopyrimidinium 2-carboxy-4,5-dichlorobenzoate, C4H6N3+·C8H3Cl2O4-, (I), 3-(aminocarbonyl)pyridinium 2-carboxy-4,5-dichlorobenzoate, C6H7N2O+·C8H3Cl2O4-, (II), and the unusual salt adduct 4-(aminocarbonyl)pyridinium 2-carboxy-4,5-dichlorobenzoate-methyl 2-carboxy-4,5-dichlorobenzoate (1/1), C6H7N2O+·C8H3Cl2O4-·C9H6Cl2O4, (III), have been determined at 130 K. Compound (I) forms discrete centrosymmetric hydrogen-bonded cyclic bis(cation-anion) units having both R22(8) and R12(4) N-HO interactions. In (II), the primary N-HO-linked cation-anion units are extended into a two-dimensional sheet structure via amide-carboxyl and amide-carbonyl N-HO interactions. The structure of (III) reveals the presence of an unusual and unexpected self-synthesized methyl monoester of the acid as an adduct molecule, giving one-dimensional hydrogen-bonded chains. In all three structures, the hydrogen phthalate anions are essentially planar with short intramolecular carboxyl-carboxylate O-HO hydrogen bonds [OO = 2.393 (8)-2.410 (2) Å]. This work provides examples of low-dimensional 1:1 hydrogen-bonded DCPA structure types, and includes the first example of a discrete cyclic `heterotetramer.' This low dimensionality in the structures of the 1:1 aromatic Lewis base salts of the parent acid is generally associated with the planar DCPA anion species.
Peer Reviewed Yes
Published Yes
Publisher URI http://www3.interscience.wiley.com/journal/117976290/home
Alternative URI http://dx.doi.org/10.1107/S0108270109004405
Copyright Statement Copyright 2009 International Union of Crystallography. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Published by Blackwell Publishing Ltd. Please refer to the journal's website for access to the definitive, published version.
Volume C65
Issue Number 3
Page from o103
Page to o107
ISSN 0108-2701
Date Accessioned 2010-05-06
Language en_AU
Faculty Faculty of Science, Environment, Engineering and Technology
Subject Physical Chemistry
URI http://hdl.handle.net/10072/30144
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1

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