Proton transfer from 2-naphthol to aliphatic amines in supercritical CO 2

The proton transfer from 2-naphthol to aliphatic amines was studied in supercritical CO 2 (scCO 2) and in cyclohexane as reference solvent, by absorption and fluorescence spectroscopy and by time-resolved emission. Irradiation of 2-naphthol in scCO 2 in the presence of ethyldiisopropylamine shows dy...

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Autores principales:	Simoncelli, S., Hoijemberg, P.A., Japas, M.L., Aramendía, P.F.
Formato:	JOUR
Materias:	2-naphthols Absorption and fluorescence spectroscopy Aliphatic amines Base-catalyzed reaction Electronic excitation Fluorescence excitation spectra Fluorescence quenching Proton donors Supercritical CO Time-resolved emissions Amines Carbon dioxide Excited states Fluorescence Fluorescence spectroscopy Proton transfer Quantum yield Phenols 2 naphthol 2-naphthol acid alkane amine carbon dioxide cyclohexane cyclohexane derivative naphthol derivative proton solvent water article catalysis chemical structure chemistry cold fluorescence hydrogen bond kinetics pH physical chemistry pressure spectrofluorometry Acids Alkanes Carbon Dioxide Catalysis Chemistry, Physical Cold Temperature Cyclohexanes Hydrogen Bonding Hydrogen-Ion Concentration Kinetics Molecular Structure Naphthols Pressure Protons Solvents Spectrometry, Fluorescence Water
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_10895639_v115_n50_p14243_Simoncelli
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_10895639_v115_n50_p14243_Simoncelli
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spelling	todo:paper_10895639_v115_n50_p14243_Simoncelli2023-10-03T16:04:44Z Proton transfer from 2-naphthol to aliphatic amines in supercritical CO 2 Simoncelli, S. Hoijemberg, P.A. Japas, M.L. Aramendía, P.F. 2-naphthols Absorption and fluorescence spectroscopy Aliphatic amines Base-catalyzed reaction Electronic excitation Fluorescence excitation spectra Fluorescence quenching Proton donors Supercritical CO Time-resolved emissions Amines Carbon dioxide Excited states Fluorescence Fluorescence spectroscopy Proton transfer Quantum yield Phenols 2 naphthol 2-naphthol acid alkane amine carbon dioxide cyclohexane cyclohexane derivative naphthol derivative proton solvent water article catalysis chemical structure chemistry cold fluorescence hydrogen bond kinetics pH physical chemistry pressure spectrofluorometry Acids Alkanes Amines Carbon Dioxide Catalysis Chemistry, Physical Cold Temperature Cyclohexanes Fluorescence Hydrogen Bonding Hydrogen-Ion Concentration Kinetics Molecular Structure Naphthols Pressure Protons Solvents Spectrometry, Fluorescence Water The proton transfer from 2-naphthol to aliphatic amines was studied in supercritical CO 2 (scCO 2) and in cyclohexane as reference solvent, by absorption and fluorescence spectroscopy and by time-resolved emission. Irradiation of 2-naphthol in scCO 2 in the presence of ethyldiisopropylamine shows dynamic fluorescence quenching of the acidic form of 2-naphthol and emission from the basic form. Fluorescence excitation spectra show that the emission of the basic form is originated upon excitation of the acidic form. The interaction between 2-naphthol and the amines is described by the formation of a complex with proton donor - acceptor character in the ground and excited states of 2-naphthol. The acidity increase of 2-naphthol upon electronic excitation to the first excited singlet in scCO 2 is as high as in water. Proton transfer quantum yields of 0.6 can be easily achieved in scCO 2. The results have implications for carrying out acid - base catalyzed reactions in scCO 2. (Figure presented) © 2011 American Chemical Society. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_10895639_v115_n50_p14243_Simoncelli
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	2-naphthols Absorption and fluorescence spectroscopy Aliphatic amines Base-catalyzed reaction Electronic excitation Fluorescence excitation spectra Fluorescence quenching Proton donors Supercritical CO Time-resolved emissions Amines Carbon dioxide Excited states Fluorescence Fluorescence spectroscopy Proton transfer Quantum yield Phenols 2 naphthol 2-naphthol acid alkane amine carbon dioxide cyclohexane cyclohexane derivative naphthol derivative proton solvent water article catalysis chemical structure chemistry cold fluorescence hydrogen bond kinetics pH physical chemistry pressure spectrofluorometry Acids Alkanes Amines Carbon Dioxide Catalysis Chemistry, Physical Cold Temperature Cyclohexanes Fluorescence Hydrogen Bonding Hydrogen-Ion Concentration Kinetics Molecular Structure Naphthols Pressure Protons Solvents Spectrometry, Fluorescence Water
spellingShingle	2-naphthols Absorption and fluorescence spectroscopy Aliphatic amines Base-catalyzed reaction Electronic excitation Fluorescence excitation spectra Fluorescence quenching Proton donors Supercritical CO Time-resolved emissions Amines Carbon dioxide Excited states Fluorescence Fluorescence spectroscopy Proton transfer Quantum yield Phenols 2 naphthol 2-naphthol acid alkane amine carbon dioxide cyclohexane cyclohexane derivative naphthol derivative proton solvent water article catalysis chemical structure chemistry cold fluorescence hydrogen bond kinetics pH physical chemistry pressure spectrofluorometry Acids Alkanes Amines Carbon Dioxide Catalysis Chemistry, Physical Cold Temperature Cyclohexanes Fluorescence Hydrogen Bonding Hydrogen-Ion Concentration Kinetics Molecular Structure Naphthols Pressure Protons Solvents Spectrometry, Fluorescence Water Simoncelli, S. Hoijemberg, P.A. Japas, M.L. Aramendía, P.F. Proton transfer from 2-naphthol to aliphatic amines in supercritical CO 2
topic_facet	2-naphthols Absorption and fluorescence spectroscopy Aliphatic amines Base-catalyzed reaction Electronic excitation Fluorescence excitation spectra Fluorescence quenching Proton donors Supercritical CO Time-resolved emissions Amines Carbon dioxide Excited states Fluorescence Fluorescence spectroscopy Proton transfer Quantum yield Phenols 2 naphthol 2-naphthol acid alkane amine carbon dioxide cyclohexane cyclohexane derivative naphthol derivative proton solvent water article catalysis chemical structure chemistry cold fluorescence hydrogen bond kinetics pH physical chemistry pressure spectrofluorometry Acids Alkanes Amines Carbon Dioxide Catalysis Chemistry, Physical Cold Temperature Cyclohexanes Fluorescence Hydrogen Bonding Hydrogen-Ion Concentration Kinetics Molecular Structure Naphthols Pressure Protons Solvents Spectrometry, Fluorescence Water
description	The proton transfer from 2-naphthol to aliphatic amines was studied in supercritical CO 2 (scCO 2) and in cyclohexane as reference solvent, by absorption and fluorescence spectroscopy and by time-resolved emission. Irradiation of 2-naphthol in scCO 2 in the presence of ethyldiisopropylamine shows dynamic fluorescence quenching of the acidic form of 2-naphthol and emission from the basic form. Fluorescence excitation spectra show that the emission of the basic form is originated upon excitation of the acidic form. The interaction between 2-naphthol and the amines is described by the formation of a complex with proton donor - acceptor character in the ground and excited states of 2-naphthol. The acidity increase of 2-naphthol upon electronic excitation to the first excited singlet in scCO 2 is as high as in water. Proton transfer quantum yields of 0.6 can be easily achieved in scCO 2. The results have implications for carrying out acid - base catalyzed reactions in scCO 2. (Figure presented) © 2011 American Chemical Society.
format	JOUR
author	Simoncelli, S. Hoijemberg, P.A. Japas, M.L. Aramendía, P.F.
author_facet	Simoncelli, S. Hoijemberg, P.A. Japas, M.L. Aramendía, P.F.
author_sort	Simoncelli, S.
title	Proton transfer from 2-naphthol to aliphatic amines in supercritical CO 2
title_short	Proton transfer from 2-naphthol to aliphatic amines in supercritical CO 2
title_full	Proton transfer from 2-naphthol to aliphatic amines in supercritical CO 2
title_fullStr	Proton transfer from 2-naphthol to aliphatic amines in supercritical CO 2
title_full_unstemmed	Proton transfer from 2-naphthol to aliphatic amines in supercritical CO 2
title_sort	proton transfer from 2-naphthol to aliphatic amines in supercritical co 2
url	http://hdl.handle.net/20.500.12110/paper_10895639_v115_n50_p14243_Simoncelli
work_keys_str_mv	AT simoncellis protontransferfrom2naphtholtoaliphaticaminesinsupercriticalco2 AT hoijembergpa protontransferfrom2naphtholtoaliphaticaminesinsupercriticalco2 AT japasml protontransferfrom2naphtholtoaliphaticaminesinsupercriticalco2 AT aramendiapf protontransferfrom2naphtholtoaliphaticaminesinsupercriticalco2
_version_	1782028199057686528

Proton transfer from 2-naphthol to aliphatic amines in supercritical CO 2

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