Characterization of Dicarboxylic Salts of Protonated Triethylenetetramine Useful for the Treatment of Copper-Related Pathologies

• Published in: Crystal growth & design Vol. 7; no. 9; pp. 1844 - 1850
• Main Authors: Wichmann, Kathrin A, Boyd, Peter D. W, Söhnel, Tilo, Allen, Grant R, Phillips, Anthony R. J, Cooper, Garth J. S
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.09.2007; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Condensed matter: structure, mechanical and thermal properties; Crystalline state (including molecular motions in solids); Crystallographic aspects of phase transformations; pressure effects; Crystallography; Exact sciences and technology; Materials Science; Materials Science, Multidisciplinary; Organic compounds; Physical Sciences; Physics; Science & Technology; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; Technology; CRYSTALLIZATION; HEART; ANION; CRYSTAL-STRUCTURE; WILSONS-DISEASE; TETRAMINE DIHYDROCHLORIDE; CHEMISTRY; RECEPTOR; Amines; Hydrogen bonds; Moisture; Thermogravimetry; Differential thermal analysis; XRD; Copper; Lattice parameters; Carboxylic acid salts; Polymorphism; Crystal structure
• ISSN: 1528-7483; 1528-7505
• DOI: 10.1021/cg0704549

X-ray crystal structures of three salts of protonated triethylenetetramine, (H4TETA)4+, with succinate, maleate, and fumarate anions are reported. Structures of the complexes (H4-triethylenetetramine)(hydrogenmaleate)4·2H2O [(H4TETA)(Hmal)4·2H2O] (1), (H4-triethylenetetramine)(hydrogenfumarate)4·3.3H2O [(H4TETA)(Hfum)4·3.3H2O] (2), and (H4-triethylenetetramine)(succinate)2 [(H4TETA)(suc)2] (3) all form assemblies of alternating two-dimensional layers of (H4TETA)4+ and the anionic species via hydrogen-bond networks. Both classical and nonclassical hydrogen bonds between the protonated amine groups, anions, and water molecules were observed. X-ray powder diffraction measurements, differential thermal analysis/thermogravimetry, density vapor sorption, and Karl Fischer titration measurements were performed to obtain confirmatory information about the water content in the structures 1 and 2 and to examine polymorphism within the salts. The nonhydrated salt 3 was determined to be the most favorable salt formulation for use in medicinal applications.