Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system
The preparation, isolation and characterization by elemental analysis and 1H-NMR, 13C-NMR, and MS data of the bromo derivatives of N-substituted carbazoles, i.e., of 9-methyl-9H-carbazole (1), 9-phenyl-9H-carbazole (2), 9-benzyl-9H-carbazole (3), 2-methoxy-9-methyl-9H- carbazole (4), and of C-substi...
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2006
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paper:paper_0018019X_v89_n6_p1123_Ponce2023-06-08T14:39:11Z Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system Bonesi, Sergio Mauricio Erra Balsells, Rosa Derivatives Fluorescence Gels Mass spectrometry Nuclear magnetic resonance Phosphorescence Silica Spectroscopic analysis Bromination Emission spectra N-bromosuccinimide (NBS) Spin-orbital-coupling Bromine compounds 2 (acetyloxy) 9h carbazole 2 methoxy 9 methyl 9h carbazole 3 nitro 9h carbazole 9 benzyl 9h carbazole 9 methyl 9h carbazole 9 phenyl 9h carbazole bromocarbazole derivative carbazole derivative n bromosuccinimide silica gel unclassified drug article bromination light absorption nuclear magnetic resonance spectroscopy phosphorescence priority journal spectroscopy The preparation, isolation and characterization by elemental analysis and 1H-NMR, 13C-NMR, and MS data of the bromo derivatives of N-substituted carbazoles, i.e., of 9-methyl-9H-carbazole (1), 9-phenyl-9H-carbazole (2), 9-benzyl-9H-carbazole (3), 2-methoxy-9-methyl-9H- carbazole (4), and of C-substituted carbazoles, i.e., of 2-(acetyloxy)-9H- carbazole (5) and 3-nitro-9H-carbazole (6), are reported, in part for the first time. As brominating reagents, N-bromosuccinimide (NBS) or NBS/silica gel in CH2Cl2, NBS in AcOH, KBrO3/KBr in EtOH doped with a catalytic amount of H2SO4, or KBrO3/KBr in AcOH were employed, and their uses were compared. Semi-empirical PM3 calculations were performed to predict the reactivity of the N-substituted and C-substituted carbazoles and of their bromo derivatives and found to verify the experimental results. The UV-absorption and fluorescence and phosphorescence emission spectra of the bromocarbazole derivatives in MeCN solution at 298 K and in a solid matrix at 77 K were compared with those of the corresponding carbazoles 1-6. The dynamic properties of the lowest excited singlet and triplet states (τf, τp, φf, and φp) were measured under the same experimental conditions. The intramolecular spin-orbital-coupling effect of the Br-atom and NO2 group on the spectroscopic data, photophysical parameters, and on the photo reactivity were also briefly analyzed. © 2006 Verlag Helvetica Chimica Acta AG. Fil:Bonesi, S.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Erra-Balsells, R. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2006 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0018019X_v89_n6_p1123_Ponce http://hdl.handle.net/20.500.12110/paper_0018019X_v89_n6_p1123_Ponce |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Derivatives Fluorescence Gels Mass spectrometry Nuclear magnetic resonance Phosphorescence Silica Spectroscopic analysis Bromination Emission spectra N-bromosuccinimide (NBS) Spin-orbital-coupling Bromine compounds 2 (acetyloxy) 9h carbazole 2 methoxy 9 methyl 9h carbazole 3 nitro 9h carbazole 9 benzyl 9h carbazole 9 methyl 9h carbazole 9 phenyl 9h carbazole bromocarbazole derivative carbazole derivative n bromosuccinimide silica gel unclassified drug article bromination light absorption nuclear magnetic resonance spectroscopy phosphorescence priority journal spectroscopy |
| spellingShingle |
Derivatives Fluorescence Gels Mass spectrometry Nuclear magnetic resonance Phosphorescence Silica Spectroscopic analysis Bromination Emission spectra N-bromosuccinimide (NBS) Spin-orbital-coupling Bromine compounds 2 (acetyloxy) 9h carbazole 2 methoxy 9 methyl 9h carbazole 3 nitro 9h carbazole 9 benzyl 9h carbazole 9 methyl 9h carbazole 9 phenyl 9h carbazole bromocarbazole derivative carbazole derivative n bromosuccinimide silica gel unclassified drug article bromination light absorption nuclear magnetic resonance spectroscopy phosphorescence priority journal spectroscopy Bonesi, Sergio Mauricio Erra Balsells, Rosa Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system |
| topic_facet |
Derivatives Fluorescence Gels Mass spectrometry Nuclear magnetic resonance Phosphorescence Silica Spectroscopic analysis Bromination Emission spectra N-bromosuccinimide (NBS) Spin-orbital-coupling Bromine compounds 2 (acetyloxy) 9h carbazole 2 methoxy 9 methyl 9h carbazole 3 nitro 9h carbazole 9 benzyl 9h carbazole 9 methyl 9h carbazole 9 phenyl 9h carbazole bromocarbazole derivative carbazole derivative n bromosuccinimide silica gel unclassified drug article bromination light absorption nuclear magnetic resonance spectroscopy phosphorescence priority journal spectroscopy |
| description |
The preparation, isolation and characterization by elemental analysis and 1H-NMR, 13C-NMR, and MS data of the bromo derivatives of N-substituted carbazoles, i.e., of 9-methyl-9H-carbazole (1), 9-phenyl-9H-carbazole (2), 9-benzyl-9H-carbazole (3), 2-methoxy-9-methyl-9H- carbazole (4), and of C-substituted carbazoles, i.e., of 2-(acetyloxy)-9H- carbazole (5) and 3-nitro-9H-carbazole (6), are reported, in part for the first time. As brominating reagents, N-bromosuccinimide (NBS) or NBS/silica gel in CH2Cl2, NBS in AcOH, KBrO3/KBr in EtOH doped with a catalytic amount of H2SO4, or KBrO3/KBr in AcOH were employed, and their uses were compared. Semi-empirical PM3 calculations were performed to predict the reactivity of the N-substituted and C-substituted carbazoles and of their bromo derivatives and found to verify the experimental results. The UV-absorption and fluorescence and phosphorescence emission spectra of the bromocarbazole derivatives in MeCN solution at 298 K and in a solid matrix at 77 K were compared with those of the corresponding carbazoles 1-6. The dynamic properties of the lowest excited singlet and triplet states (τf, τp, φf, and φp) were measured under the same experimental conditions. The intramolecular spin-orbital-coupling effect of the Br-atom and NO2 group on the spectroscopic data, photophysical parameters, and on the photo reactivity were also briefly analyzed. © 2006 Verlag Helvetica Chimica Acta AG. |
| author |
Bonesi, Sergio Mauricio Erra Balsells, Rosa |
| author_facet |
Bonesi, Sergio Mauricio Erra Balsells, Rosa |
| author_sort |
Bonesi, Sergio Mauricio |
| title |
Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system |
| title_short |
Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system |
| title_full |
Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system |
| title_fullStr |
Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system |
| title_full_unstemmed |
Synthesis and electronic spectroscopy of bromocarbazoles. Direct bromination of N- and C-substituted carbazoles by N-bromosuccinimide or a N-bromosuccinimide/silica gel system |
| title_sort |
synthesis and electronic spectroscopy of bromocarbazoles. direct bromination of n- and c-substituted carbazoles by n-bromosuccinimide or a n-bromosuccinimide/silica gel system |
| publishDate |
2006 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0018019X_v89_n6_p1123_Ponce http://hdl.handle.net/20.500.12110/paper_0018019X_v89_n6_p1123_Ponce |
| work_keys_str_mv |
AT bonesisergiomauricio synthesisandelectronicspectroscopyofbromocarbazolesdirectbrominationofnandcsubstitutedcarbazolesbynbromosuccinimideoranbromosuccinimidesilicagelsystem AT errabalsellsrosa synthesisandelectronicspectroscopyofbromocarbazolesdirectbrominationofnandcsubstitutedcarbazolesbynbromosuccinimideoranbromosuccinimidesilicagelsystem |
| _version_ |
1768544024166137856 |