Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives

The study of the intra- and intermolecular interactions in the solid state of four related fluorine-containing 1,2,3-triazole derivatives (1: R = –H, 2: R = –NO2, 3: R = –CH3, 4: R = –Cl) was carried out using quantum chemical calculations, vibrational (IR and Raman) and solid phase UV-vis spectrosc...

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Detalles Bibliográficos
Autores principales: Espitia Cogollo, Edeimis, Piro, Oscar Enrique, Echeverría, Gustavo Alberto, Tuttolomondo, M. E., Pérez, Hiram, Jios, Jorge Luis, Ulic, Sonia Elizabeth
Formato: Articulo
Lenguaje:Inglés
Publicado: 2020
Materias:
Química
Ciencias Exactas
X-ray crystal structure
molecular interactions
NBO intermolecular energies
Hirshfeld surface analysis
Pixel energies
vibrational spectroscopy
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/141466
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-141466
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Química
Ciencias Exactas
X-ray crystal structure
molecular interactions
NBO intermolecular energies
Hirshfeld surface analysis
Pixel energies
vibrational spectroscopy
spellingShingle Química
Ciencias Exactas
X-ray crystal structure
molecular interactions
NBO intermolecular energies
Hirshfeld surface analysis
Pixel energies
vibrational spectroscopy
Espitia Cogollo, Edeimis
Piro, Oscar Enrique
Echeverría, Gustavo Alberto
Tuttolomondo, M. E.
Pérez, Hiram
Jios, Jorge Luis
Ulic, Sonia Elizabeth
Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives
topic_facet Química
Ciencias Exactas
X-ray crystal structure
molecular interactions
NBO intermolecular energies
Hirshfeld surface analysis
Pixel energies
vibrational spectroscopy
description The study of the intra- and intermolecular interactions in the solid state of four related fluorine-containing 1,2,3-triazole derivatives (1: R = –H, 2: R = –NO2, 3: R = –CH3, 4: R = –Cl) was carried out using quantum chemical calculations, vibrational (IR and Raman) and solid phase UV-vis spectroscopy, and single-crystal X-ray diffraction methods. The enol–keto/keto–enol tautomerism on the o-hydroxyacetophenone moiety was analyzed in terms of the synergy between O–H⋯O intramolecular hydrogen bond strengthening and the enhancement of π delocalization within the pseudo ring. The preference of the enol–keto form was attributed to the aromatic stabilization energy. The proton in the triazole ring was located on the intermediate nitrogen atom, with no evidence of prototropy in the studied series. Compounds 1 and 4 have similar structural motifs with N–H⋯O hydrogen bonds connecting amino and carbonyl groups of neighboring molecules in a chain along the a-axis. For 2, it was found that both oxygen atoms of the nitro substituent participate as acceptors, connecting adjacent molecules by hydrogen bonds through the N–H and O–H groups. In compound 3, the crystallization water molecule dominates the hydrogen bonding interactions, which associates three molecules of 3, giving rise to a three-dimensional H-bonding network. These intra and intermolecular interactions, which affect the absorption band locations of the involved groups, were also detected in the vibrational spectra of the studied triazoles.
format Articulo
Articulo
author Espitia Cogollo, Edeimis
Piro, Oscar Enrique
Echeverría, Gustavo Alberto
Tuttolomondo, M. E.
Pérez, Hiram
Jios, Jorge Luis
Ulic, Sonia Elizabeth
author_facet Espitia Cogollo, Edeimis
Piro, Oscar Enrique
Echeverría, Gustavo Alberto
Tuttolomondo, M. E.
Pérez, Hiram
Jios, Jorge Luis
Ulic, Sonia Elizabeth
author_sort Espitia Cogollo, Edeimis
title Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives
title_short Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives
title_full Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives
title_fullStr Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives
title_full_unstemmed Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives
title_sort hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives
publishDate 2020
url http://sedici.unlp.edu.ar/handle/10915/141466
work_keys_str_mv AT espitiacogolloedeimis hydrogenbondinginteractionsinfluorinated123triazolederivatives
AT pirooscarenrique hydrogenbondinginteractionsinfluorinated123triazolederivatives
AT echeverriagustavoalberto hydrogenbondinginteractionsinfluorinated123triazolederivatives
AT tuttolomondome hydrogenbondinginteractionsinfluorinated123triazolederivatives
AT perezhiram hydrogenbondinginteractionsinfluorinated123triazolederivatives
AT jiosjorgeluis hydrogenbondinginteractionsinfluorinated123triazolederivatives
AT ulicsoniaelizabeth hydrogenbondinginteractionsinfluorinated123triazolederivatives
bdutipo_str Repositorios
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