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3,5-Dinitrosalicylic acid in Molecular assembly. III. Proton-transfer compounds of 3,5-dinitrosalicylic acid with polycyclic aromatic and heteroaromatic amines, and overall series structural systematics

Smith, Graham, Wermuth, Urs D., Healy, Peter C., & White, Jonathan M. (2007) 3,5-Dinitrosalicylic acid in Molecular assembly. III. Proton-transfer compounds of 3,5-dinitrosalicylic acid with polycyclic aromatic and heteroaromatic amines, and overall series structural systematics. Australian Journal of Chemistry, 60(4), pp. 264-277.

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Abstract

The crystal structures of the 1:1 proton-transfer compounds of 3,5-dinitrosalicylic acid (dnsa) with a series of common polycyclic aromatic and heteroaromatic anines (quinoline, 1-naphthylamine, 1,2,3,4-tetrahydroquinoline, quinaldic acid, benzamidazole, 1,10-phenanthroline and 2,2'-bipyridine) have been determined and the hydrogen-bonding associations in each analyzed. The compounds are [(C9H8N)+ (dnsa)-] (1), [(C10H10N)+ (dnsa)-] (2), [(C9H12N)+ (dnsa)-] (3), [(C10H8NO2)+ (dnsa)-] (4), [(C7H7N2)+ (dnsa)-] (5), [(C12H9N2)+ (dnsa)-] (6), [(C10H9N2)+ (dnsa)-] (7).In all compounds, protonation of either the substituent amino group or the hetero-N of the Lewis base occurs, with subsequent hydrogen bonding via this and other hydrogen donors variously to the carboxylate, phenate and nitro oxygen acceptors of the dnsa anions. The result is the formation of primary N+-H...O associations which with secondary peripheral interactions, which within this set of compounds includes an increased incidence of aromatic C-H...O associations, give framework polymer structures. In three of the compounds [1,4 and 6], , cation-anion pi-pi interactions are also found. The completion of this series of compounds has now allowed the categorization of the molecular assembly modes in the proton-transfer compounds of 3,5-dinitrosalicylic acid.

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ID Code: 7612
Item Type: Journal Article
Additional Information: For more information, please refer to the journal’s website (see link) or contact the author. Author contact details: g.smith@qut.edu.au
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Keywords: proton, transfer compounds, 3, 5, dinitrosalicylic acid, molecular assembly
DOI: 10.1071/CH06276
ISSN: 0004-9425
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > PHYSICAL CHEMISTRY (INCL. STRUCTURAL) (030600) > Structural Chemistry and Spectroscopy (030606)
Divisions: Past > QUT Faculties & Divisions > Faculty of Science and Technology
Current > Research Centres > Science Research Centre
Copyright Owner: Copyright 2007 CSIRO
Deposited On: 11 May 2007
Last Modified: 01 Mar 2012 09:10

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