A resonance-assisted intra-molecular hydrogen bond in compounds containing 2-hy-droxy-3,5-di-nitro-benzoic acid and its various deprotonated forms: redetermination of several related structures.

ABSTRACT: A large number of structural determinations of compounds containing 2-hy-droxy-3,5-di-nitro-benzoic acid (I) and its various deprotonated forms, 2-hy-droxy-3,5-di-nitro-benzoate (II) or 2-carb-oxy-4,6-di-nitro-phenolate (III), are biased. The reason for the bias follows from incorrectly applied constraints or restraints on the bridging hydrogen, which is involved in the intra-molecular hydrogen bond between the neighbouring carb-oxy-lic/carboxyl-ate and oxo/hy-droxy groups. This hydrogen bond belongs to the category of resonance-assisted hydrogen bonds. The present article suggests corrections for the following structure determinations that have been published in Acta Crystallographica: DUJZAK, JEVNAA, LUDFUL, NUQVEB, QIQJAD, SAFGUD, SEDKET, TIYZIM, TUJPE

SUBMITTER: Fabry J 

PROVIDER: S-EPMC6127720 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature