Show simple item record

dc.contributor.authorSmith, Graham
dc.contributor.authorWermuth, Urs D
dc.date.accessioned2017-05-03T12:38:59Z
dc.date.available2017-05-03T12:38:59Z
dc.date.issued2010
dc.date.modified2012-03-15T05:43:36Z
dc.identifier.issn0108-2701
dc.identifier.doi10.1107/S010827011004672X
dc.identifier.urihttp://hdl.handle.net/10072/37583
dc.description.abstractThe structures of the anhydrous 1:1 proton-transfer compounds of isonipecotamide (4-carbamoylpiperidine) with picric acid and 3,5-dinitrosalicylic acid, namely 4-carbamoylpiperidinium 2,4,6-trinitrophenolate, C6H13N2O8 + C6H2N3O7 - (I) and 4-carbamoylpiperidinium 2-carboxy-4,6-dinitrophenolate, C6H13N2O8 + C7H3N2O7 -: two forms, the monoclinic a-polymorph (II) and the triclinic ߭polymorph (III) have been determined at 200 K. All compounds form hydrogen-bonded structures, one-dimensional in (II), two-dimensional in (I) and threedimensional in (III). In (I), the cations form centrosymmetric cyclic head-to-tail hydrogen-bonded homodimers [graph set R2 2(14)] through lateral duplex piperidinium N-H緷Oamide interactions. These dimers are extended into a two-dimensional network structure through further interactions with anion phenolate-O and nitro-O acceptors, including a direct symmetric piperidinium N-H緷Ophenol,Onitro cation-anion association [graph set R2 1(6)]. The monoclinic polymorph (II) has a similar R2 1(6) cation-anion hydrogen-bonding interaction to (I) but with an additional conjoint symmetrical R1 2(4) interaction as well as head-to-tail piperidinium N-H緷Oamide O hydrogen bonds and amide N-H緷Ocarboxyl hydrogen bonds, give a network structure which include large R3 4(20) rings. The hydrogen bonding in the triclinic polymorph (III) is markedly different from that of monoclinic (II). The asymmetric unit contains two independent cation-anion pairs which associate through cyclic piperidinium N-H緷O,O'carboxyl interactions [graph set R2 1(4)]. The cations also show the zig-zag head-to-tail piperidinium N-H緷Oamidehydrogen-bonded chain substructures found in (II) but in addition feature amide N- H緷Onitro and Ophenolate and amide N-H緷Onitro associations. As well there is a centrosymmetric double-amide N -H緷Ocarboxyl bridged bis(cation-anion) ring system [graph set R2 4(8)] in the three-dimensional framework. The structures reported here demonstrate the utility of the isonipecotamide cation as a synthon with previously unrecognized potential for structure assembly applications. Furthermore, the structures of the two polymorphic 3,5-dinitrosalicylic acid salts show an unusual dissimilarity in hydrogen-bonding characteristics, considering that both were obtained from identical solvent systems.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.format.extent458960 bytes
dc.format.mimetypeapplication/pdf
dc.languageEnglish
dc.language.isoeng
dc.publisherWiley-Blackwell Publishing, Inc.
dc.publisher.placeUnited States
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom609
dc.relation.ispartofpageto613
dc.relation.ispartofissue12
dc.relation.ispartofjournalActa Crystallographica Section C: Crystal Structure Communications
dc.relation.ispartofvolume66
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.titleAnhydrous 1:1 proton-transfer compounds of isonipecotamide with picric acid and 3,5-dinitrosalicylic acid: 4-carbamoylpiperidinium 2,4,6-trinitrophenolate and two polymorphs of 4-carbamoylpiperidinium 2-carboxy-4,6-dinitrophenolate
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.rights.copyright© 2010 International Union of Crystallography. Published by Blackwell Publishing Ltd. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Please refer to the journal's website for access to the definitive, published version.
gro.date.issued2010
gro.hasfulltextFull Text
gro.griffith.authorWermuth, Urs D.


Files in this item

This item appears in the following Collection(s)

  • Journal articles
    Contains articles published by Griffith authors in scholarly journals.

Show simple item record