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Artículo

A new perfluoromethyl aminoenone derivative and the role of the hydrogen bonding in the intra- and intermolecular interactions

Rocha, MarianaIcon ; Gil, Diego MauricioIcon ; Echeverría, Gustavo AlbertoIcon ; Piro, Oscar EnriqueIcon ; Jios, Jorge Luis; Ulic, Sonia ElizabethIcon
Fecha de publicación: 01/2018
Editorial: Elsevier Science Sa
Revista: Journal of Fluorine Chemistry
ISSN: 0022-1139
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:
Otras Ciencias Químicas

Resumen

The structure of a new perfluoromethyl derivative, (Z)-4,4,4-trifluoro-1-(2-hydroxyphenyl)-3-(methylamino)-2-buten-1-one (1), was investigated in both crystalline state and solution since the prototropy enable the existence of three tautomeric species in equilibrium. The preference in the configurational E/Z arrangement is strongly dependent on the intramolecular hydrogen bond interactions. The vibrational and electronic spectra of 1 were discussed and assigned by using DFT calculations. The crystal, solved by single-crystal X-ray diffraction, shows the prevalence of the tautomer aminoenone over the imino-enol and imino-ketone forms. Therefore, an almost planar molecular conformation is observed due to the formation of two intramolecular amino and phenolic hydrogen bonds to the same carbonyl oxygen acceptor atom that stabilize the Z configuration. The molecular packing is held by the O-H⋯O(keto) and N-H⋯O hydrogen bonds, F⋯F, C-H⋯π and π-stacking interactions that contribute to the crystal stabilization. The intra and intermolecular contacts were also characterized by Natural Bond Orbital (NBO) analysis and Atoms in Molecules (AIM) approach. Hirshfeld surfaces and their associated fingerprint plots were generated for 1 and for a related structure, to visualize different intermolecular interactions and their relative contributions to the total surface.
Palabras clave: β-AMINOENONE TAUTOMER , CRYSTAL STRUCTURE , DFT CALCULATIONS , HYDROGEN BONDING , HIRSHFELD SURFACE ANALYSIS
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info:eu-repo/semantics/openAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)
Identificadores
URI: http://hdl.handle.net/11336/85516
URL: http://linkinghub.elsevier.com/retrieve/pii/S0022113917305286
URL: https://doi.org/10.1016/j.jfluchem.2018.01.001
Colecciones
Articulos(CEQUINOR)
Articulos de CENTRO DE QUIMICA INORGANICA "DR. PEDRO J. AYMONINO"
Articulos(IFLP)
Articulos de INST.DE FISICA LA PLATA
Articulos(INQUINOA)
Articulos de INST.DE QUIMICA DEL NOROESTE
Citación
Rocha, Mariana; Gil, Diego Mauricio; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis; et al.; A new perfluoromethyl aminoenone derivative and the role of the hydrogen bonding in the intra- and intermolecular interactions; Elsevier Science Sa; Journal of Fluorine Chemistry; 208; 1-2018; 36-47
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