Add time:07/26/2019         Source:sciencedirect.com

Four organic salt complexes of 3-hydroxypyridine (3-HP) with nitro-substituted aromatic and heterocyclic carboxylic acids have been prepared and their X-ray crystal structures reported. These complexes are 3-hydroxypyridinium 5-nitrofuran-2-carboxylate 1, 3-hydroxypyridinium 4-nitrobenzoate 2, 3-hydroxypyridinium 2,4-dinitrobenzoate 3, and 3-hydroxypyridinium 3,5-dinitrobenzoate 4. The hydrogen-bonding networks in each are dominated by interactions from both the protonated heterocyclic nitrogen and the 3-hydroxy group on 3-HP to the carboxylate oxygens. The principal structural unit in complexes 1 and 3 is a tetramer consisting of two of each component molecule, whereas in complexes 2 and 4 the hydrogen-bonded polymers are observed. In all cases additional CH···O interactions to the nitro oxygens are present and add to the hydrogen-bonding array. A review of three previous 3-HP salt structures as well as the four presented in this paper reveals that the hydrogen-bonding distances between nonhydrogen atoms from the heterocyclic nitrogen of 3-HP is slightly longer than that from the 3-hydroxy group [av. 2.658(5) and 2.594(5)].

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