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dc.contributor.authorSmith, Grahamen_US
dc.contributor.authorWermuth, Ursen_US
dc.contributor.authorM. White, Jonathanen_US
dc.date.accessioned2017-04-24T13:26:48Z
dc.date.available2017-04-24T13:26:48Z
dc.date.issued2009en_US
dc.date.modified2010-06-15T05:30:49Z
dc.identifier.issn01082701en_US
dc.identifier.doi10.1107/S0108270109004405en_AU
dc.identifier.urihttp://hdl.handle.net/10072/30144
dc.description.abstractThe 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+烸H3Cl2O4-, (I), 3-(aminocarbonyl)pyridinium 2-carboxy-4,5-dichlorobenzoate, C6H7N2O+烸H3Cl2O4-, (II), and the unusual salt adduct 4-(aminocarbonyl)pyridinium 2-carboxy-4,5-dichlorobenzoate-methyl 2-carboxy-4,5-dichlorobenzoate (1/1), C6H7N2O+烸H3Cl2O4-烹H6Cl2O4, (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) ŝ. 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.en_US
dc.description.peerreviewedYesen_US
dc.description.publicationstatusYesen_AU
dc.format.extent86742 bytes
dc.format.mimetypeapplication/pdf
dc.languageEnglishen_US
dc.language.isoen_AU
dc.publisherWiley-Blackwell Publishing, Inc.en_US
dc.publisher.placeUnited Statesen_US
dc.publisher.urihttp://www3.interscience.wiley.com/journal/117976290/homeen_AU
dc.relation.ispartofstudentpublicationNen_AU
dc.relation.ispartofpagefromo103en_US
dc.relation.ispartofpagetoo107en_US
dc.relation.ispartofissue3en_US
dc.relation.ispartofjournalActa Crystallographica. Section C: Crystal Structure Communicationsen_US
dc.relation.ispartofvolumeC65en_US
dc.rights.retentionYen_AU
dc.subject.fieldofresearchPhysical Chemistry not elsewhere classifieden_US
dc.subject.fieldofresearchcode030699en_US
dc.titleZero-, 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 isonicotinamideen_US
dc.typeJournal articleen_US
dc.type.descriptionC1 - Peer Reviewed (HERDC)en_US
dc.type.codeC - Journal Articlesen_US
gro.rights.copyrightCopyright 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.en_AU
gro.date.issued2009
gro.hasfulltextFull Text


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