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 = -NO 2 , 3 : R = -CH 3 , 4 : R = -Cl) was carried out using quantum chemical calculations, vibrational (IR and Raman) and solid phase UV-vis...

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Bibliographic Details
Published in:New journal of chemistry 2020-10, Vol.44 (37), p.166-1619
Main Authors: Espitia Cogollo, E, Piro, O. E, Echeverría, G. A, Tuttolomondo, M. E, Pérez, H, Jios, J. L, Ulic, S. E
Format: Article
Language:English
Subjects:
Absorption spectra
Carbonyl groups
Carbonyls
Chemical bonds
Crystal structure
Crystallization
Crystallography
Derivatives
Dimers
Electron transitions
Electronic spectra
Energy
EREP
Fluorine
Hydrogen bonding
Hydrogen bonds
Lattice vibration
Mathematical analysis
Molecular orbitals
Parameters
Quantum chemistry
Room temperature
Single crystals
Solid phases
Spectrum analysis
Vibration mode
Vibrational spectra
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Summary: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 = -NO 2 , 3 : R = -CH 3 , 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. Comprehensive theoretical, structural and spectroscopic investigations on new substituted 1,2,3-triazoles in the solid state.
ISSN:1144-0546
1369-9261
DOI:10.1039/d0nj02914a