5-Nitrosalicylic Acid and its Proton-Transfer Compounds with Aliphatic Lewis Bases
Graham Smith A E , Andy W. Hartono A , Urs D. Wermuth A , Peter C. Healy B , Jonathan M. White C and A. David Rae DA School of Physical and Chemical Sciences, Queensland University of Technology, Brisbane QLD 4001, Australia.
B School of Science, Griffith University, Nathan QLD 4111, Australia.
C School of Chemistry, University of Melbourne, Parkville VIC 3010, Australia.
D Research School of Chemistry, Australian National University, Canberra ACT 0200, Australia.
E Corresponding author. Email: g.smith@qut.edu.au
Australian Journal of Chemistry 58(1) 47-52 https://doi.org/10.1071/CH04144
Submitted: 9 June 2004 Accepted: 5 October 2004 Published: 14 January 2005
Abstract
The crystal structures of the proton-transfer compounds of 5-nitrosalicylic acid (5-nsa) with morpholine (morph), hexamethylenetetramine (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+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 mirror 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.
Acknowledgments
The authors acknowledge financial support from the Australian Research Council, the School of Physical and Chemical Sciences, Queensland University of Technology, the School of Chemistry, University of Melbourne, and the School of Science, Griffith University. Dr Tony Willis at the Research School of Chemistry, Australian National University, is thanked for collection of CCD data on compound 2.
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