Outer-sphere electron transfer from carbazoles to halomethanes. Reduction potentials of halomethanes measured by fluorescence quenching experiments.

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Kinetic studies on the photoinduced electron transfer reduction of a variety of halomethanes in acetonitrile and ethanol at 298 K are reported in terms of the quenching rate constants (kq) with a series of reductants (carbazoles and anthracenes) whose one-electron oxidation potentials (Eox) have bee...

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Autor principal: Bonesi, S.M
Otros Autores: Erra-Balsells, R.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2000
Acceso en línea:Registro en Scopus
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100 1 |a Bonesi, S.M. 
245 1 0 |a Outer-sphere electron transfer from carbazoles to halomethanes. Reduction potentials of halomethanes measured by fluorescence quenching experiments. 
260 |c 2000 
270 1 0 |m Erra-Balsells, R.; Depto. de Quimica Organica, FCEyN-UBA, Pabellon 2, 3 Ciudad Universitaria, 1428 Buenos Aires, Argentina; email: erra@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
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520 3 |a Kinetic studies on the photoinduced electron transfer reduction of a variety of halomethanes in acetonitrile and ethanol at 298 K are reported in terms of the quenching rate constants (kq) with a series of reductants (carbazoles and anthracenes) whose one-electron oxidation potentials (Eox) have been measured again in the present work vs. SCE and independently vs. ferrocene. The Rehm-Weller Gibbs energy relationship is applied to determine the fundamental parameters for the one-electron reduction, i.e., the one-electron reduction potentials (ERX/RẊ) of the halomethanes and the intrinsic barrier for the electron transfer reduction (ΔG‡o). The ERX/RX-̇ values obtained were related to the concerted electron transfer-bond breaking reduction potentials (ERX/R·+x-) and the standard free enthalpies of dissociation of RX-̇ (ΔGo,dissRX-̇) were estimated in each solvent. Additionally, the one-electron reduction potential (ERX/RX-̇) values estimated in acetonitrile were also related to different thermodynamic parameters such as electron affinity (EA), LUMO-HOMO energy differences (ΔE) and the bond dissociation energy (DRX). Optimized geometry, EA and ΔE for halomethanes were calculated by an ab initio method at the B3LYP level using 3-21G, 6-31 + G(d,p) and G-311 + G(3df,2pd) basis sets. In all these cases good linear correlations were obtained. The ΔG‡o values obtained are compared with those calculated using the equation ΔG‡o = λ/4 with λ = λi + λo where the solvent reorganization energy (λo) and the inner-sphere reorganization energies (λi) associated with the structural change upon the electron-transfer process were calculated, the former by using the Marcus-Hush model and the latter by using semiempirical and ab initio molecular modeling and QSAR properties. Results obtained from the preparative irradiation of carbazoles in the presence of halomethanes, which are consistent with a photoinduced electron transfer mechanism are also discussed.  |l eng 
593 |a Depto. de Quimica Organica, FCEyN-UBA, Pabellon 2, 3 Ciudad Universitaria, 1428 Buenos Aires, Argentina 
690 1 0 |a CHARGE TRANSFER 
690 1 0 |a DISSOCIATION 
690 1 0 |a ELECTRON TRANSPORT PROPERTIES 
690 1 0 |a ENTHALPY 
690 1 0 |a FLUORESCENCE 
690 1 0 |a GIBBS FREE ENERGY 
690 1 0 |a IRRADIATION 
690 1 0 |a MATHEMATICAL MODELS 
690 1 0 |a MOLECULAR DYNAMICS 
690 1 0 |a QUENCHING 
690 1 0 |a RATE CONSTANTS 
690 1 0 |a REDUCTION 
690 1 0 |a CARBAZOLES 
690 1 0 |a ELECTRON TRANSFER 
690 1 0 |a HALOMETHANES 
690 1 0 |a SOLVENT REORGANIZATION ENERGY 
690 1 0 |a ORGANIC COMPOUNDS 
700 1 |a Erra-Balsells, R. 
773 0 |d 2000  |h pp. 1583-1595  |k n. 7  |p J Chem Soc Perkin Trans 2  |x 03009580  |w (AR-BaUEN)CENRE-119  |t Journal of the Chemical Society. Perkin Transactions 2 
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856 4 0 |u https://hdl.handle.net/20.500.12110/paper_03009580_v_n7_p1583_Bonesi  |y Handle 
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