Polar and steric effects of substituents in aromatic nucleophilic substitution. Reactions of 4-, 5-, and 6-substituted 1-chloro-2-nitrobenzenes with sodium thiophenoxide in methanol
The kinetics of the reactions of 4-, 5-, and 6-substituted 1-chloro-2-nitrobenzenes with sodium thiophenoxide in methanol have been determined, and the thermodynamic parameters, energy and entropy of activation, calculated. For the 5-substituted series a plot of log k against σ-values gave a ρ-value...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00456470_v_n_p963_Porto |
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todo:paper_00456470_v_n_p963_Porto2023-10-03T14:51:56Z Polar and steric effects of substituents in aromatic nucleophilic substitution. Reactions of 4-, 5-, and 6-substituted 1-chloro-2-nitrobenzenes with sodium thiophenoxide in methanol Porto, A.M. Altieri, L. Castro, A.J. Brieux, J.A. The kinetics of the reactions of 4-, 5-, and 6-substituted 1-chloro-2-nitrobenzenes with sodium thiophenoxide in methanol have been determined, and the thermodynamic parameters, energy and entropy of activation, calculated. For the 5-substituted series a plot of log k against σ-values gave a ρ-value + 5·15. The σ4-Subst values corresponding to this reaction have been estimated by regression. For the 6-substituted-series a plot of log k6-Subst against σ4-Subst parameters gave a ρ-value + 3.46 showing that the polar influence of an ortho-substitutent predominates over its steric effects. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00456470_v_n_p963_Porto |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| description |
The kinetics of the reactions of 4-, 5-, and 6-substituted 1-chloro-2-nitrobenzenes with sodium thiophenoxide in methanol have been determined, and the thermodynamic parameters, energy and entropy of activation, calculated. For the 5-substituted series a plot of log k against σ-values gave a ρ-value + 5·15. The σ4-Subst values corresponding to this reaction have been estimated by regression. For the 6-substituted-series a plot of log k6-Subst against σ4-Subst parameters gave a ρ-value + 3.46 showing that the polar influence of an ortho-substitutent predominates over its steric effects. |
| format |
JOUR |
| author |
Porto, A.M. Altieri, L. Castro, A.J. Brieux, J.A. |
| spellingShingle |
Porto, A.M. Altieri, L. Castro, A.J. Brieux, J.A. Polar and steric effects of substituents in aromatic nucleophilic substitution. Reactions of 4-, 5-, and 6-substituted 1-chloro-2-nitrobenzenes with sodium thiophenoxide in methanol |
| author_facet |
Porto, A.M. Altieri, L. Castro, A.J. Brieux, J.A. |
| author_sort |
Porto, A.M. |
| title |
Polar and steric effects of substituents in aromatic nucleophilic substitution. Reactions of 4-, 5-, and 6-substituted 1-chloro-2-nitrobenzenes with sodium thiophenoxide in methanol |
| title_short |
Polar and steric effects of substituents in aromatic nucleophilic substitution. Reactions of 4-, 5-, and 6-substituted 1-chloro-2-nitrobenzenes with sodium thiophenoxide in methanol |
| title_full |
Polar and steric effects of substituents in aromatic nucleophilic substitution. Reactions of 4-, 5-, and 6-substituted 1-chloro-2-nitrobenzenes with sodium thiophenoxide in methanol |
| title_fullStr |
Polar and steric effects of substituents in aromatic nucleophilic substitution. Reactions of 4-, 5-, and 6-substituted 1-chloro-2-nitrobenzenes with sodium thiophenoxide in methanol |
| title_full_unstemmed |
Polar and steric effects of substituents in aromatic nucleophilic substitution. Reactions of 4-, 5-, and 6-substituted 1-chloro-2-nitrobenzenes with sodium thiophenoxide in methanol |
| title_sort |
polar and steric effects of substituents in aromatic nucleophilic substitution. reactions of 4-, 5-, and 6-substituted 1-chloro-2-nitrobenzenes with sodium thiophenoxide in methanol |
| url |
http://hdl.handle.net/20.500.12110/paper_00456470_v_n_p963_Porto |
| work_keys_str_mv |
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