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dc.contributor.authorSmith, Graham
dc.contributor.authorWermuth, Urs D
dc.contributor.authorWhite, Jonathan M
dc.date.accessioned2017-05-03T15:51:55Z
dc.date.available2017-05-03T15:51:55Z
dc.date.issued2009
dc.date.modified2010-06-15T05:30:49Z
dc.identifier.issn0108-2701
dc.identifier.doi10.1107/S0108270109004405
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.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.format.extent86742 bytes
dc.format.mimetypeapplication/pdf
dc.languageEnglish
dc.language.isoeng
dc.publisherWiley-Blackwell Publishing, Inc.
dc.publisher.placeUnited States
dc.publisher.urihttps://onlinelibrary.wiley.com/iucr/doi/10.1107/S0108270109004405
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefromo103
dc.relation.ispartofpagetoo107
dc.relation.ispartofissue3
dc.relation.ispartofjournalActa Crystallographica. Section C: Crystal Structure Communications
dc.relation.ispartofvolumeC65
dc.rights.retentionY
dc.subject.fieldofresearchInorganic chemistry
dc.subject.fieldofresearchPhysical chemistry
dc.subject.fieldofresearchPhysical chemistry not elsewhere classified
dc.subject.fieldofresearchOther chemical sciences
dc.subject.fieldofresearchcode3402
dc.subject.fieldofresearchcode3406
dc.subject.fieldofresearchcode340699
dc.subject.fieldofresearchcode3499
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 isonicotinamide
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.rights.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.
gro.date.issued2009
gro.hasfulltextFull Text
gro.griffith.authorWermuth, Urs D.


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