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  • Title: Three-dimensional hydrogen-bonded structures in the 1:1 proton-transfer compounds of L-tartaric acid with the associative-group monosubstituted pyridines 3-aminopyridine, 3-carboxypyridine (nicotinic acid) and 2-carboxypyridine (picolinic acid).
    Author: Smith G, Wermuth UD.
    Journal: Acta Crystallogr C; 2010 Jan; 66(Pt 1):o5-10. PubMed ID: 20048425.
    Abstract:
    The 1:1 proton-transfer compounds of L-tartaric acid with 3-aminopyridine [3-aminopyridinium hydrogen (2R,3R)-tartrate dihydrate, C(5)H(7)N(2)(+).C(4)H(5)O(6)(-).2H(2)O, (I)], pyridine-3-carboxylic acid (nicotinic acid) [anhydrous 3-carboxypyridinium hydrogen (2R,3R)-tartrate, C(6)H(6)NO(2)(+).C(4)H(5)O(6)(-), (II)] and pyridine-2-carboxylic acid [2-carboxypyridinium hydrogen (2R,3R)-tartrate monohydrate, C(6)H(6)NO(2)(+).C(4)H(5)O(6)(-).H(2)O, (III)] have been determined. In (I) and (II), there is a direct pyridinium-carboxyl N(+)-H...O hydrogen-bonding interaction, four-centred in (II), giving conjoint cyclic R(1)(2)(5) associations. In contrast, the N-H...O association in (III) is with a water O-atom acceptor, which provides links to separate tartrate anions through O(hydroxy) acceptors. All three compounds have the head-to-tail C(7) hydrogen-bonded chain substructures commonly associated with 1:1 proton-transfer hydrogen tartrate salts. These chains are extended into two-dimensional sheets which, in hydrates (I) and (III) additionally involve the solvent water molecules. Three-dimensional hydrogen-bonded structures are generated via crosslinking through the associative functional groups of the substituted pyridinium cations. In the sheet structure of (I), both water molecules act as donors and acceptors in interactions with separate carboxyl and hydroxy O-atom acceptors of the primary tartrate chains, closing conjoint cyclic R(4)(4)(8), R(3)(4)(11) and R(3)(3)(12) associations. Also, in (II) and (III) there are strong cation carboxyl-carboxyl O-H...O hydrogen bonds [O...O = 2.5387 (17) A in (II) and 2.441 (3) A in (III)], which in (II) form part of a cyclic R(2)(2)(6) inter-sheet association. This series of heteroaromatic Lewis base-hydrogen L-tartrate salts provides further examples of molecular assembly facilitated by the presence of the classical two-dimensional hydrogen-bonded hydrogen tartrate or hydrogen tartrate-water sheet substructures which are expanded into three-dimensional frameworks via peripheral cation bifunctional substituent-group crosslinking interactions.
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