TY - JOUR
T1 - 5-nitrosalicylic acid and its proton-transfer compounds with aliphatic lewis bases
AU - Smith, Graham
AU - Hartono, Andy W.
AU - Wermuth, Urs D.
AU - Healy, Peter C.
AU - White, Jonathan M.
AU - Rae, A. David
PY - 2005
Y1 - 2005
N2 - The crystal structures of the proton-transfer compounds of 5-nitrosalicylic acid (5-nsa) with morpholine (morph), hexamethylenetetraminc (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+(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 minor 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.
AB - The crystal structures of the proton-transfer compounds of 5-nitrosalicylic acid (5-nsa) with morpholine (morph), hexamethylenetetraminc (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+(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 minor 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.
UR - http://www.scopus.com/inward/record.url?scp=13444261286&partnerID=8YFLogxK
U2 - 10.1071/CH04144
DO - 10.1071/CH04144
M3 - Article
SN - 0004-9425
VL - 58
SP - 47
EP - 52
JO - Australian Journal of Chemistry
JF - Australian Journal of Chemistry
IS - 1
ER -