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Interactions of aromatic carboxylic acids with 8-aminoquinoline: Synthesis and the crystal structures of the proton-transfer compounds of 8-aminoquinoline with nitro-substituted benzoic acids

Smith, Graham; Wen, Daying; Bott, R; White, Jonathan; Willis, Anthony

Description

Proton-transfer compounds of 8-aminoquinoline with the nitro-substituted aromatic carboxylic acids 3-nitrobenzoic acid, [(C9H9N2+)(C7 H4NO4-)] (1), 4-nitrobenzoic acid, [(C9H9N2+) (C7H5NO4)] (2), 3,5-dinitrobenzoic acid, [(C9H9N2+)(C7 H3N2O6-)] (3), 5-nitrosalicylic acid, [(C9H9N2+) (C7H4NO5-)] (4) and 3,5-dinitrosalicylic acid, [(C9H9N2+) (C7H3N2O7-)] (5) have been prepared and characterized by using both infrared spectroscopy and single-crystal X-ray diffraction methods [(1) (4) and (5)]. In...[Show more]

dc.contributor.authorSmith, Graham
dc.contributor.authorWen, Daying
dc.contributor.authorBott, R
dc.contributor.authorWhite, Jonathan
dc.contributor.authorWillis, Anthony
dc.date.accessioned2015-12-13T23:27:22Z
dc.date.available2015-12-13T23:27:22Z
dc.identifier.issn0004-9425
dc.identifier.urihttp://hdl.handle.net/1885/93297
dc.description.abstractProton-transfer compounds of 8-aminoquinoline with the nitro-substituted aromatic carboxylic acids 3-nitrobenzoic acid, [(C9H9N2+)(C7 H4NO4-)] (1), 4-nitrobenzoic acid, [(C9H9N2+) (C7H5NO4)] (2), 3,5-dinitrobenzoic acid, [(C9H9N2+)(C7 H3N2O6-)] (3), 5-nitrosalicylic acid, [(C9H9N2+) (C7H4NO5-)] (4) and 3,5-dinitrosalicylic acid, [(C9H9N2+) (C7H3N2O7-)] (5) have been prepared and characterized by using both infrared spectroscopy and single-crystal X-ray diffraction methods [(1) (4) and (5)]. In all compounds, protonation of the quinoline nitrogen occurs together with primary hydrogen-bonding interactions involving this group and the carboxylate group of the acid, while further peripheral associations result predominantly in simple chain polymeric structures. The attempted preparation of the adduct with 2,4,6-trinitrobenzoic acid gave the unstable, neutral, essentially 1:1 adduct with the decarboxylation product 1,3,5-trinitrobenzene, the X-ray crystal structure of which indicates the stoichiometry [(C9H8N2)0.6(C6 H3N3O6)0.8] (6).
dc.publisherCSIRO Publishing
dc.sourceAustralian Journal of Chemistry
dc.subjectKeywords: Amines; Aromatic compounds; Charge transfer; Crystal structure; Hydrogen bonds; Infrared spectroscopy; Nitrogen compounds; Protons; Stoichiometry; Substitution reactions; Synthesis (chemical); X ray diffraction analysis; Adduct; Aminoquinoline; Aromatic c
dc.titleInteractions of aromatic carboxylic acids with 8-aminoquinoline: Synthesis and the crystal structures of the proton-transfer compounds of 8-aminoquinoline with nitro-substituted benzoic acids
dc.typeJournal article
local.description.notesImported from ARIES
local.description.refereedYes
local.identifier.citationvolume54
dc.date.issued2001
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationMigratedxPub26709
local.type.statusPublished Version
local.contributor.affiliationSmith, Graham, Queensland University of Technology
local.contributor.affiliationWen, Daying, James Cook University
local.contributor.affiliationBott, R, Queensland University of Technology
local.contributor.affiliationWhite, Jonathan, University of Melbourne
local.contributor.affiliationWillis, Anthony, College of Physical and Mathematical Sciences, ANU
local.bibliographicCitation.issue3
local.bibliographicCitation.startpage165
local.bibliographicCitation.lastpage170
local.identifier.doi10.1071/CH01010
dc.date.updated2015-12-12T09:50:03Z
local.identifier.scopusID2-s2.0-0034874659
CollectionsANU Research Publications

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