title: Crystal structure and aqueous solubility of ammonium D-glucarate.
abstract: Ammonium D-glucarate, NH(4)(C(6)H(9)O(8)) [ammonium D-saccharate, NH(4)-SAC], has been synthesized, and its crystal structure solved by single-crystal X-ray diffraction methods. NH(4)-SAC crystallizes in the monoclinic space group P2(1) (#4) with cell parameters a = 4.8350(4) Angstroms, b = 11.0477(8) Angstroms, c = 16.7268(12) Angstroms, beta = 90.973(1) degrees, V = 894.34(12) Angstroms(3), Z = 3. The structure was refined by full-matrix least-squares on F(2) yielding final R-values (all data) R1 = 0.0353 and R(w)2 = 0.0870. The structure consists of alternating (NH(4))(+) and (C(6)H(11)O(6))(-) layers parallel to the bc plane. An extended network of N-H...O(SAC) and O(SAC)-H...O(SAC) hydrogen bonds provide the 3-D connectivity. The aqueous solubility (S(w)) has been shown to be pH independent at ambient conditions within the range 4.5 < pH < 10 with S(w) = 2.19 M/L, whose value is about a factor of two lower than that of the ammonium isosaccharate analogue.
authors.affiliation: Sandia National Laboratories, Albuquerque, NM 87185-0779, USA. rpbontc@sandia.gov
authors.forename: Ranko P
authors.initials: RP
authors.lastname: Bontchev
authors.forename: Robert C
authors.initials: RC
authors.lastname: Moore
mesh_terms: D018360:Crystallography, X-Ray; D004355:Drug Stability; D005937:Glucaric Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D006358:Hot Temperature; D006860:Hydrogen Bonding; D012995:Solubility; D014867:Water
chemical_list: D014867:Water; D005937:Glucaric Acid