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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2011
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10895639_v115_n50_p14243_Simoncelli http://hdl.handle.net/20.500.12110/paper_10895639_v115_n50_p14243_Simoncelli |
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paper:paper_10895639_v115_n50_p14243_Simoncelli2023-06-08T16:06:30Z Proton transfer from 2-naphthol to aliphatic amines in supercritical CO 2 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. 2011 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10895639_v115_n50_p14243_Simoncelli 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 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. |
| 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 |
| publishDate |
2011 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10895639_v115_n50_p14243_Simoncelli http://hdl.handle.net/20.500.12110/paper_10895639_v115_n50_p14243_Simoncelli |
| _version_ |
1768542751036538880 |