TY - JOUR
T1 - The 1:1 proton-transfer compounds of 4-(phenyldiazenyl)aniline (aniline yellow) with 3-nitrophthalic, 4-nitrophthalic and 5-nitroisophthalic acids
AU - Smith, Graham
AU - Wermuth, Urs D.
AU - Young, David J.
AU - White, Jonathan M.
PY - 2008/3/12
Y1 - 2008/3/12
N2 - The structures of the anhydrous 1:1 proton-transfer compounds of the dye precursor aniline yellow [4-(phenyldiazenyl)-aniline], namely isomeric 4-(phenyldiazenyl)-anilinium 2-carb-oxy-6-nitrobenzoate, C12H12N3+·C8H4NO6-, (I), and 4-(phenyldiazenyl)-anilinium 2-carboxy-4-nitrobenzoate, C12H12N3+·C8H4NO6-, (II), and 4-(phenyldiazenyl)anilinium 3-carboxy-5-nitrobenzoate monohydrate, C12H12N3+·C8H4NO6-·H2O, (III), have been determined at 130 K. In (I) the cation has longitudinal rotational disorder. All three compounds have substructures comprising backbones formed through strong head-to-tail carboxyl-carboxyl-ate hydrogen-bond interactions [graph set C(7) in (I) and (II), and C(8) in (III)]. Two-dimensional sheet structures are formed in all three compounds by the incorporation of the 4-(phenyldiazenyl)anilinium cations into the substructures, including, in the cases of (I) and (II), infinite H - N - H to carboxylate O-C-O group interactions [graph set C(6)], and in the case of (III), bridging through the water molecule of solvation. The peripheral alternating aromatic ring residues of both cations and anions give only weakly π-interactive step features which lie between the sheets.
AB - The structures of the anhydrous 1:1 proton-transfer compounds of the dye precursor aniline yellow [4-(phenyldiazenyl)-aniline], namely isomeric 4-(phenyldiazenyl)-anilinium 2-carb-oxy-6-nitrobenzoate, C12H12N3+·C8H4NO6-, (I), and 4-(phenyldiazenyl)-anilinium 2-carboxy-4-nitrobenzoate, C12H12N3+·C8H4NO6-, (II), and 4-(phenyldiazenyl)anilinium 3-carboxy-5-nitrobenzoate monohydrate, C12H12N3+·C8H4NO6-·H2O, (III), have been determined at 130 K. In (I) the cation has longitudinal rotational disorder. All three compounds have substructures comprising backbones formed through strong head-to-tail carboxyl-carboxyl-ate hydrogen-bond interactions [graph set C(7) in (I) and (II), and C(8) in (III)]. Two-dimensional sheet structures are formed in all three compounds by the incorporation of the 4-(phenyldiazenyl)anilinium cations into the substructures, including, in the cases of (I) and (II), infinite H - N - H to carboxylate O-C-O group interactions [graph set C(6)], and in the case of (III), bridging through the water molecule of solvation. The peripheral alternating aromatic ring residues of both cations and anions give only weakly π-interactive step features which lie between the sheets.
UR - http://www.scopus.com/inward/record.url?scp=40449127931&partnerID=8YFLogxK
U2 - 10.1107/S0108270108001595
DO - 10.1107/S0108270108001595
M3 - Article
C2 - 18322335
AN - SCOPUS:40449127931
VL - C64
SP - o123-o127
JO - Acta Crystallographica Section C: Structural Chemistry
JF - Acta Crystallographica Section C: Structural Chemistry
SN - 1600-5759
IS - Part 3
ER -