The Effect of Deoxyfluorination on Intermolecular Interactions in the Crystal Structures of 1,6-Anhydro-2,3-epimino-hexopyranoses

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F22%3A00551216" target="_blank" >RIV/67985858:_____/22:00551216 - isvavai.cz</a>

Alternative codes found

RIV/00216208:11310/22:10445281

Result on the web

<a href="https://mdpi-res.com/d_attachment/molecules/molecules-27-00278/article_deploy/molecules-27-00278.pdf?version=1641202020" target="_blank" >https://mdpi-res.com/d_attachment/molecules/molecules-27-00278/article_deploy/molecules-27-00278.pdf?version=1641202020</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/molecules27010278" target="_blank" >10.3390/molecules27010278</a>

Result language

angličtina

Original language name

The Effect of Deoxyfluorination on Intermolecular Interactions in the Crystal Structures of 1,6-Anhydro-2,3-epimino-hexopyranoses

Original language description

The effect of substitution on intermolecular interactions was investigated in a series of 1,6-anhydro-2,3-epimino-hexopyranoses. The study focused on the qualitative evaluation of intermolecular interactions using DFT calculations and the comparison of molecular arrangements in the crystal lattice. Altogether, ten crystal structures were compared, including two structures of C4-deoxygenated, four C4-deoxyfluorinated and four parent epimino pyranoses. It was found that the substitution of the original hydroxy group by hydrogen or fluorine leads to a weakening of the intermolecular interaction by approximately 4 kcal/mol. The strength of the intermolecular interactions was found to be in the following descending order: hydrogen bonding of hydroxy groups, hydrogen bonding of the amino group, interactions with fluorine and weak electrostatic interactions. The intermolecular interactions that involved fluorine atom were rather weak, however, they were often supported by other weak interactions. The fluorine atom was not able to substitute the role of the hydroxy group in molecular packing and the fluorine atoms interacted only weakly with the hydrogen atoms located at electropositive regions of the carbohydrate molecules. However, the fluorine interaction was not restricted to a single molecule but was spread over at least three other molecules. This feature is a base for similar molecule arrangements in the structures of related compounds, as we found for the C4-Fax and C4-Feq epimines presented here.

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

10401 - Organic chemistry

Project

—

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2022

Confidentiality

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

Name of the periodical

Molecules

ISSN

1420-3049

e-ISSN

1420-3049

Volume of the periodical

27

Issue of the periodical within the volume

1

Country of publishing house

CH - SWITZERLAND

Number of pages

17

Pages from-to

278

UT code for WoS article

000813898400001

EID of the result in the Scopus database

2-s2.0-85122133826