Smith Graham, Wermuth Urs D, White Jonathan M
School of Physical and Chemical Sciences, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia.
Acta Crystallogr C. 2008 Sep;64(Pt 9):o532-6. doi: 10.1107/S0108270108027054. Epub 2008 Aug 29.
The crystal structures of the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with the three isomeric monoaminobenzoic acids, namely the hydrate 2-carboxyanilinium 2-carboxy-4,5-dichlorobenzoate dihydrate, C(7)H(8)NO(2)(+).C(8)H(3)Cl(2)O(4)(-).2H(2)O, (I), and the anhydrous salts 3-carboxyanilinium 2-carboxy-4,5-dichlorobenzoate, C(7)H(8)NO(2)(+).C(8)H(3)Cl(2)O(4)(-), (II), and 4-carboxyanilinium 2-carboxy-4,5-dichlorobenzoate, C(7)H(8)NO(2)(+).C(8)H(3)Cl(2)O(4)(-), (III), have been determined at 130 K. Compound (I) has a two-dimensional hydrogen-bonded sheet structure, while (II) and (III) are three-dimensional. All three compounds feature sheet substructures formed through anilinium N(+)-H...O(carboxyl) and anion carboxylic acid O-H...O(carboxyl) interactions and, in the case of (I), additionally linked through the donor and acceptor associations of the solvent water molecules. However, (II) and (III) have additional lateral extensions of these substructures though cyclic R(2)(2)(8) associations involving the carboxylic acid groups of the cations. Also, (II) and (III) have cation-anion pi-pi aromatic ring interactions. This work provides further examples illustrating the regular formation of network substructures in the 1:1 proton-transfer salts of 4,5-dichlorophthalic acid with the bifunctional aromatic amines.
已在130 K下测定了4,5-二氯邻苯二甲酸与三种异构单氨基苯甲酸形成的1:1质子转移化合物的晶体结构，即水合物2-羧基苯胺鎓2-羧基-4,5-二氯苯甲酸二水合物，C(7)H(8)NO(2)(+)·C(8)H(3)Cl(2)O(4)(-)·2H(2)O，(I)，以及无水盐3-羧基苯胺鎓2-羧基-4,5-二氯苯甲酸，C(7)H(8)NO(2)(+)·C(8)H(3)Cl(2)O(4)(-)，(II)，和4-羧基苯胺鎓2-羧基-4,5-二氯苯甲酸，C(7)H(8)NO(2)(+)·C(8)H(3)Cl(2)O(4)(-)，(III)。化合物(I)具有二维氢键层状结构，而(II)和(III)是三维的。所有三种化合物都具有通过苯胺鎓N(+)-H…O(羧基)和阴离子羧酸O-H…O(羧基)相互作用形成的层状子结构，并且在(I)的情况下，还通过溶剂水分子的供体和受体缔合连接。然而，(II)和(III)通过涉及阳离子羧酸基团的环状R(2)(2)(8)缔合使这些子结构具有额外的横向延伸。此外，(II)和(III)具有阳离子-阴离子π-π芳香环相互作用。这项工作提供了进一步的例子，说明了4,5-二氯邻苯二甲酸与双功能芳香胺形成的1:1质子转移盐中网络子结构的规则形成。
