title: Three hydrates of the bisphosphonate risedronate, consisting of one molecular and two ionic structures.
abstract: Three different hydrates of risedronate were obtained by varying the pH of a solution containing the compound. At the pH values used, the N atom of the pyridine group is protonated and the compounds are zwitterionic. Crystals obtained directly from the synthesis resulted in risedronate monohydrate, or [1-hydroxy-1-phosphono-2-(pyridinium-3-yl)ethyl]phosphonate monohydrate, C(7)H(11)NO(7)P(2).H(2)O, (I), in which just one phosphonate group is negatively charged. Recrystallizations at pH values of 2 and 4 yielded risedronate dihydrate, or sodium [1-hydroxy-2-(pyridinium-3-yl)ethane-1,2-diyl]bis(phosphonate) dihydrate, Na(+).C(7)H(10)NO(7)P(2)(-).2H(2)O, (II). Finally, recrystallizations at pH values of 7 and 8 produced risedronate 2.5-hydrate, or sodium [1-hydroxy-2-(pyridinium-3-yl)ethane-1,2-diyl]bis(phosphonate) 2.5-hydrate, Na(+).C(7)H(10)NO(7)P(2)(-).2.5H(2)O, (III). At these four pH values, both phosphonate groups in (II) and (III) are negatively charged and coordinated to an Na(+) ion. Crystals of (II), i.e. those grown at pH values of 2 and 4, have isomorphous polymeric ion aggregate structures with geminal phosphonate and alcohol groups coordinated to the same Na(+) ion. On the other hand, crystals of (III), i.e. those grown at pH values of 7 and 8, have isomorphism polymeric ion aggregate structures with geminal phosphonate and alcohol groups coordinated to different Na(+) ions.
authors.affiliation: Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.
authors.forename: William L
authors.initials: WL
authors.lastname: Gossman
authors.forename: Scott R
authors.initials: SR
authors.lastname: Wilson
authors.forename: Eric
authors.initials: E
authors.lastname: Oldfield
mesh_terms: D000409:Alanine / Q000737:chemistry; D018360:Crystallography, X-Ray; D012968:Etidronic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D005682:Gadolinium / Q000737:chemistry; D006860:Hydrogen Bonding; D008958:Models, Molecular; D011392:Proline / Q000737:chemistry; D000068296:Risedronic Acid
chemical_list: D011392:Proline; D005682:Gadolinium; D000068296:Risedronic Acid; D012968:Etidronic Acid; D000409:Alanine