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.
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.
Impact and interest:
Citation countsare sourced monthly fromand citation databases.
Citations counts from theindexing service can be viewed at the linked Google Scholar™ search.
Full-text downloadsdisplays the total number of times this work’s files (e.g., a PDF) have been downloaded from QUT ePrints as well as the number of downloads in the previous 365 days. The count includes downloads for all files if a work has more than one.
|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: firstname.lastname@example.org|
|Keywords:||proton, transfer compounds, 3, 5, dinitrosalicylic acid, molecular assembly|
|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|
Repository Staff Only: item control page