A resonance-assisted intramolecular hydrogen bond in compounds containing 2-hydroxy-3,5-dinitrobenzoic acid and its various deprotonated forms: redetermination of several related structures

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68378271%3A_____%2F18%3A00494870" target="_blank" >RIV/68378271:_____/18:00494870 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1107/S2056989018011544" target="_blank" >http://dx.doi.org/10.1107/S2056989018011544</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1107/S2056989018011544" target="_blank" >10.1107/S2056989018011544</a>

Result language

angličtina

Original language name

A resonance-assisted intramolecular hydrogen bond in compounds containing 2-hydroxy-3,5-dinitrobenzoic acid and its various deprotonated forms: redetermination of several related structures

Original language description

A large number of structural determinations of compounds containing 2-hydroxy-3,5-dinitrobenzoic acid (I) and its various deprotonated forms, 2-hydroxy-3,5-dinitrobenzoate (II) or 2-carboxy-4,6-dinitrophenolate (III), are biased. The reason for the bias follows from incorrectly applied constraints or restraints on the bridging hydrogen, which is involved in the intramolecular hydrogen bond between the neighbouring carboxylic/carboxylate and oxo/hydroxy groups. This hydrogen bond belongs to the category of resonance assisted hydrogen bonds. In some cases, it is disordered between the two O atoms. The position of the bridging hydrogen seems to be dependent on the pKa(base) although with exceptions. A stronger basicity enhances the probability of the presence of a phenolate (III). It appears that the best model, in many cases, is obtained by fixing the hydrogen-atom position found in the difference electron-density map while refining its isotropic displacement parameter.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10302 - Condensed matter physics (including formerly solid state physics, supercond.)

Project

<a href="/en/project/LO1603" target="_blank" >LO1603: Centre of Technology and Advanced Structure Analysis of Materials with Application Impact</a><br>

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2018

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Acta Crystallographica section E - Crystallographic Communications

ISSN

2056-9890

e-ISSN

—

Volume of the periodical

74

Issue of the periodical within the volume

Sep

Country of publishing house

GB - UNITED KINGDOM

Number of pages

14

Pages from-to

1344-1357

UT code for WoS article

000443407400035

EID of the result in the Scopus database

2-s2.0-85053063471