Acta Crystallographica Section B

Structural Science

Volume 59, Part 1 (February 2003)

research papers

Acta Cryst. (2003). B59, 100-117 [ doi:10.1107/S0108768102020219 ]

Salts of maleic and fumaric acids with organic polyamines: comparison of isomeric acids as building blocks in supramolecular chemistry

K. F. Bowes, G. Ferguson, A. J. Lough and C. Glidewell

Abstract: Maleic acid and fumaric acid both readily form adducts with organic diamines: maleic acid usually forms 2:1 adducts with bases, while fumaric acid usually forms 1:1 adducts, and the supramolecular stuctures within the two series are not simply related. The 1:2 adducts formed by 1,2-bis(4-pyridyl)ethane and by 4,4'-bipyridyl, respectively, with maleic acid, compounds (1) and (2), are salts [{(diamine)H₂}²⁺]·[(C₄H₃O₄)^-]₂ in which the cations lie across a centre of inversion and a twofold rotation axis, respectively. The ions are linked by N-HO hydrogen bonds into three-ion aggregates, which are further linked by C-HO hydrogen bonds into two- and three-dimensional arrays, respectively. In the fumarate salts formed by 2,2'-dipyridylamine (1:1) and 1,4-diazabicyclo[2.2.2]octane (1:2), compounds (3) and (4), the ionic components are linked into molecular ladders. The 1:1 adduct of 4,4'-bipyridyl and fumaric acid, compound (5), contains two neutral components, both of which lie across centres of inversion; these components are linked into chains by a single O-HN hydrogen bond and thence into sheets by C-HO hydrogen bonds. The corresponding adduct formed by 1,4-diazabicyclo[2.2.2]octane, compound (6), is a salt that again contains chains linked into sheets by C-HO hydrogen bonds. In the 1:1 adducts, compounds (7), (8) and (10), that are formed between 1,2-bis(4-pyridyl)ethane, 4,4'-trimethylenedipyridine and hexamethylenetetramine, respectively, with fumaric acid, and in the 1:2 adduct, compound (9), of 2,2'-dipyridylamine and maleic acid, the chains that are generated by the hard hydrogen bonds are linked by C-HO hydrogen bonds to form, in each case, a single three-dimensional framework. In the 1:1 adduct, compound (11), of 2,2'-bipyridyl and fumaric acid the hydrogen bonds generate two interwoven three-dimensional frameworks.

Keywords: maleic acid; fumaric acid; organic diamines; hydrogen bonding; supramolecular structures.


	Structure factor file (CIF format) (109.9 kbytes) Contains datablock I

	Structure factor file (CIF format) (93.0 kbytes) Contains datablock II

	Structure factor file (CIF format) (148.2 kbytes) Contains datablock III

	Structure factor file (CIF format) (83.4 kbytes) Contains datablock IV

	Structure factor file (CIF format) (67.9 kbytes) Contains datablock V

	Structure factor file (CIF format) (117.0 kbytes) Contains datablock VI

	Structure factor file (CIF format) (81.6 kbytes) Contains datablock VII

	Structure factor file (CIF format) (87.9 kbytes) Contains datablock VIII

	Structure factor file (CIF format) (122.0 kbytes) Contains datablock IX

	Structure factor file (CIF format) (124.3 kbytes) Contains datablock X

	Structure factor file (CIF format) (77.6 kbytes) Contains datablock XI

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