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

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Smith, G
Hartono, AW
Wermuth, UD
Healy, PC
White, JM
Rae, AD
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2005
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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)-爲O] 2, and [(en)2+2(5-nsa)-爲O] 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緷O hydrogen bonds only to the water molecules with peripheral weak hmt C-H緷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.

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Australian Journal of Chemistry

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58

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1

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Chemical sciences

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