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

Graham Smith; Urs D. Wermuth; Peter C. Healy; Jonathan M. White

doi:10.1071/CH06276

RESEARCH ARTICLE

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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

Graham Smith ^A ^D , Urs D. Wermuth ^A , Peter C. Healy ^B and Jonathan M. White ^C

+ Author Affiliations

- Author Affiliations

^A School of Physical and Chemical Sciences, Queensland University of Technology, Brisbane QLD 4001, Australia.

^B School of Biomolecular and Physical Sciences, Griffith University, Nathan QLD 4111, Australia.

^C BIO-21, Molecular Science and Biotechnology, University of Melbourne, Parkville VIC 3010, Australia.

^D Corresponding author. Email: g.smith@qut.edu.au

Australian Journal of Chemistry 60(4) 264-277 https://doi.org/10.1071/CH06276
Submitted: 2 August 2006 Accepted: 21 March 2007 Published: 26 April 2007

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 amines (quinoline, 1-naphthylamine, 1,2,3,4-tetrahydroquinoline, quinaldic acid, benzimidazole, 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, and [(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 π–π 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.

Acknowledgments

The authors acknowledge financial support from the School of Physical and Chemical Sciences, Queensland University of Technology, the School of Biomolecular and Physical Sciences, Griffith University, and the School of Chemistry, University of Melbourne.

References

^* Part II, Aust. J. Chem. 2003, 56, 707.^[ ¹ ^]

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

Abstract

Acknowledgments

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