Acta Crystallographica Section B

Structural Science

Volume 59, Part 1 (February 2003)

research papers

Acta Cryst. (2003). B59, 87-99 [ doi:10.1107/S010876810201858X ]

Phosphonoacetic acid as a building block in supramolecular chemistry: salts with organic polyamines

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

Abstract: Phosphonoacetic acid, (HO)₂P(O)CH₂COOH, forms adducts with a range of amines. The acid component in these adducts may be the neutral molecule C₂H₅O₅P, the mono-anion (C₂H₄O₅P)^- or the di-anion (C₂H₃O₅P)^2-. The substructure formed by the acid component takes the form of simple chains in compounds (1)-(3), which are the 1:1 adducts formed with 1,4-diazabicyclo[2.2.2]octane, 4,4'-bipyridyl and 1,3-trimethylenedipiperidine, respectively. These adducts contain C₂H₅O₅P, (C₂H₄O₅P)^- and (C₂H₃O₅P)^2-, respectively, although (3) is solvated by a mixture of methanol and water. The (C₂H₄O₅P)^- anion substructure in (4), which is the adduct formed with meso-5,5,7,12,12,14-hexa-C-methyl-1,4,8,11-tetraazacyclotetradecane, is a chain of spiro-fused rings, while the substructure in (5), which is the adduct formed with 2,2'-dipyridylamine, is a chain of edge-fused rings. In (6), the adduct formed with 1,2-bis(4'-pyridyl)ethane, the anion substructure is two-dimensional. The chain substructures are linked by the amine units into two-dimensional structures in (1) and (4) and into three-dimensional frameworks in (2), (3) and (5), while the anion sheets in (6) are likewise linked by the amine units into a three-dimensional framework.

Keywords: phosphonoacetic acid; supramolecular chemistry; organic polyamines.