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5-Nitrosalicylic acid and its proton-transfer compounds with aliphatic Lewis bases

Smith, Graham; Hartono, Andy; Wen, Daying; Healy, Peter; White, Jonathan; Rae, A David

Description

The crystal structures of the proton-transfer compounds of 5-nitrosalicylic acid (5-nsa) with morpholine (morph), hexamethylenetetraminc (hmt), and ethylenediamine (en) have been determined and their solid-state packing structures described. The compounds are [(morph)+(5-nsa) -] 1, [(hmt)+(5-nsa)-·H2O] 2, and [(en)2+(5-nsa)-·H2O] 3. In all compounds, protonation of the hetero-nitrogen of the Lewis base occurs. With 1, the 5-nsa anions and the morpholine cations lie, respectively, in or across...[Show more]

dc.contributor.authorSmith, Graham
dc.contributor.authorHartono, Andy
dc.contributor.authorWen, Daying
dc.contributor.authorHealy, Peter
dc.contributor.authorWhite, Jonathan
dc.contributor.authorRae, A David
dc.date.accessioned2015-12-13T22:34:29Z
dc.date.available2015-12-13T22:34:29Z
dc.identifier.issn0004-9425
dc.identifier.urihttp://hdl.handle.net/1885/76143
dc.description.abstractThe crystal structures of the proton-transfer compounds of 5-nitrosalicylic acid (5-nsa) with morpholine (morph), hexamethylenetetraminc (hmt), and ethylenediamine (en) have been determined and their solid-state packing structures described. The compounds are [(morph)+(5-nsa) -] 1, [(hmt)+(5-nsa)-·H2O] 2, and [(en)2+(5-nsa)-·H2O] 3. In all compounds, protonation of the hetero-nitrogen of the Lewis base occurs. With 1, the 5-nsa anions and the morpholine cations lie, respectively, in or across crystallographic mirror planes and are linked within the planes by hydrogen-bonding interactions through the aminium group and the carboxylic and phenolic oxygens of the anionic 5-nsa species giving a two-dimensional sheet polymer. Compound 2 is an unusual structure with the planar 5-nsa anions lying within pseudo minor planes and cyclically linked by duplex water bridges through a single carboxylate oxygen into centrosymmetric dimers. The hmt cation molecules are disordered across the pseudo mirror and are strongly linked by N+-H ... O hydrogen bonds only to the water molecules with peripheral weak hmt C-H ... O hydrogen bonds extending the dimer within and between the dimer planes. Compound 3 is a network polymer comprised of the 5-nsa anions, the en dianions, and the water molecule in an extensive hydrogen-bonded structure.
dc.publisherCSIRO Publishing
dc.sourceAustralian Journal of Chemistry
dc.subjectKeywords: Charge transfer; Crystal structure; Dimers; Hydrogen bonds; Molecular structure; Negative ions; Protons; Aliphatic Lewis bases; Dianions; Proton-transfer compounds; Water bridges; Carboxylic acids
dc.title5-Nitrosalicylic acid and its proton-transfer compounds with aliphatic Lewis bases
dc.typeJournal article
local.description.notesImported from ARIES
local.description.refereedYes
local.identifier.citationvolume58
dc.date.issued2005
local.identifier.absfor030606 - Structural Chemistry and Spectroscopy
local.identifier.ariespublicationMigratedxPub5025
local.type.statusPublished Version
local.contributor.affiliationSmith, Graham, Queensland University of Technology
local.contributor.affiliationHartono, Andy, Queensland University of Technology
local.contributor.affiliationWen, Daying, James Cook University
local.contributor.affiliationHealy, Peter, Griffith University
local.contributor.affiliationWhite, Jonathan, University of Melbourne
local.contributor.affiliationRae, A David, College of Physical and Mathematical Sciences, ANU
local.bibliographicCitation.issue1
local.bibliographicCitation.startpage47
local.bibliographicCitation.lastpage52
local.identifier.doi10.1071/CH04144
dc.date.updated2015-12-11T09:21:31Z
local.identifier.scopusID2-s2.0-13444261286
CollectionsANU Research Publications

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