The Hydrogen-Bond Continuum in the Salt/Cocrystal Systems of Quinoline and Chloro-Nitrobenzoic Acids

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F24%3A00597651" target="_blank" >RIV/61388963:_____/24:00597651 - isvavai.cz</a>

Alternative codes found

RIV/00216208:11310/24:10483725 RIV/60461373:22310/24:43930287

Result on the web

<a href="https://doi.org/10.1002/chem.202402946" target="_blank" >https://doi.org/10.1002/chem.202402946</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/chem.202402946" target="_blank" >10.1002/chem.202402946</a>

Result language

angličtina

Original language name

The Hydrogen-Bond Continuum in the Salt/Cocrystal Systems of Quinoline and Chloro-Nitrobenzoic Acids

Original language description

This study investigates the hydrogen-bond geometry in six two-component solid systems composed of quinoline and chloro-nitrobenzoic acids. New X-ray diffraction studies were conducted using both the conventional independent-atom model and the more recent Hirshfeld atom-refinement method, with the latter providing precise hydrogen-atom positions. The systems can be divided into salts (the hydrogen atom transferred to the quinoline nitrogen), cocrystals (the hydrogen atom retained by the acid), and intermediate structures. Solid-state NMR experiments corroborated the X-ray diffraction-derived H-N distances. DFT calculations, using five functionals including hybrid B3LYP and PBE0, showed varying energy profiles for the hydrogen bonds, with notable differences across functionals. These calculations revealed different preferences for salt or cocrystal structures, depending on the functional used. Path-integral molecular dynamics simulations incorporating nuclear quantum effects demonstrated significant hydrogen-atom delocalization, forming a hydrogen-bond continuum, and provided average N-H distances in excellent agreement with experimental results. This comprehensive experimental and theoretical approach highlights the complexity of multicomponent solids. The study emphasizes that the classification into salts or cocrystals is frequently inadequate, as the hydrogen atom is often significantly delocalized in the hydrogen bond. This insight is crucial for understanding and predicting the behavior of such systems in pharmaceutical applications.

Czech name

—

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

10403 - Physical chemistry

Project

<a href="/en/project/GA22-15374S" target="_blank" >GA22-15374S: Proton transfer reactions studied by NMR spectroscopy and advanced quantum-chemical calculations</a><br>

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2024

Confidentiality

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

Name of the periodical

Chemistry - A European Journal

ISSN

0947-6539

e-ISSN

1521-3765

Volume of the periodical

30

Issue of the periodical within the volume

68

Country of publishing house

DE - GERMANY

Number of pages

11

Pages from-to

e202402946

UT code for WoS article

001332307100001

EID of the result in the Scopus database

2-s2.0-85206579246