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Centrosymmetric and Noncentrosymmetric R44(12) Rings As Primary Motifs in Salts of Sulfonate Anions and Chiral Primary Ammonium Cations: Their Occurrence in Hydrates, Nonhydrates, and the Zöllner Illusion

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journal contribution
posted on 06.05.2009, 00:00 by Andreas Lemmerer, Susan A. Bourne, Manuel A. Fernandes
The acid−base reaction of naphthalene-1,5-disulfonic acid and naphthalene-2-sulfonic acid with homochiral (R)-1-phenylethylamine or (S)-1-phenylethylamine or heterochiral (RS)-1-phenethylamine give rise to 9 new organic salts: ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (2), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (3), ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (4), ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (5), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (6) ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (7), ((R)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (8), ((S)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (9) and ((RS)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (10). All nine ammonium sulfonate salts have different 1-D hydrogen bonded columns, some containing water molecules (24), which are made up of different sequences of hydrogen bonded rings. The most common hydrogen bonded ring formed by the ammonium and sulfonate ions has graph set notation R44(12). Structures 27 have the columns linked to form 2-D hydrogen bonded sheets and 810 have simple 1-D chains. The results of this work as well as an analysis of the Cambridge Structural Database indicate that the R44(12) is a dominant motif in crystals composed of ammonium sulfonate salts in the same way that R22(8) is the dominant motif in carboxylic acids.

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