Aromatic nucleophilic substitutions with o- and p-fluoronitrobenzenes in aprotic solvents. Steric effects on the base-catalysed step
The kinetics of the reaction between o- and p-fluoronitrobenzene with n- and iso-propylamine were studied in toluene and DMSO at several amine concentrations and temperatures in the range 30-100°C. The results show that contrary to the previous assumption, primary steric effects due to branching in...
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1986
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1472779X_v_n5_p695_Nudelman http://hdl.handle.net/20.500.12110/paper_1472779X_v_n5_p695_Nudelman |
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paper:paper_1472779X_v_n5_p695_Nudelman2025-07-30T18:53:10Z Aromatic nucleophilic substitutions with o- and p-fluoronitrobenzenes in aprotic solvents. Steric effects on the base-catalysed step Cerdeira, Silvia Beatriz The kinetics of the reaction between o- and p-fluoronitrobenzene with n- and iso-propylamine were studied in toluene and DMSO at several amine concentrations and temperatures in the range 30-100°C. The results show that contrary to the previous assumption, primary steric effects due to branching in the amine do not produce a large decrease in the reaction rate when the first step is rate determining. However, reactions with bulky amines can be extremely slow because of the reduced power of the amine as a hydrogen-bond acceptor catalyst, when the second step is rate determining. The reaction rate may be increased by the addition of a non-nucleophilic base or another hydrogen-bond acceptor catalyst such as dimethyl sulphoxide. Fil:Cerdeira, S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 1986 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1472779X_v_n5_p695_Nudelman http://hdl.handle.net/20.500.12110/paper_1472779X_v_n5_p695_Nudelman |
| 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 reaction between o- and p-fluoronitrobenzene with n- and iso-propylamine were studied in toluene and DMSO at several amine concentrations and temperatures in the range 30-100°C. The results show that contrary to the previous assumption, primary steric effects due to branching in the amine do not produce a large decrease in the reaction rate when the first step is rate determining. However, reactions with bulky amines can be extremely slow because of the reduced power of the amine as a hydrogen-bond acceptor catalyst, when the second step is rate determining. The reaction rate may be increased by the addition of a non-nucleophilic base or another hydrogen-bond acceptor catalyst such as dimethyl sulphoxide. |
| author |
Cerdeira, Silvia Beatriz |
| spellingShingle |
Cerdeira, Silvia Beatriz Aromatic nucleophilic substitutions with o- and p-fluoronitrobenzenes in aprotic solvents. Steric effects on the base-catalysed step |
| author_facet |
Cerdeira, Silvia Beatriz |
| author_sort |
Cerdeira, Silvia Beatriz |
| title |
Aromatic nucleophilic substitutions with o- and p-fluoronitrobenzenes in aprotic solvents. Steric effects on the base-catalysed step |
| title_short |
Aromatic nucleophilic substitutions with o- and p-fluoronitrobenzenes in aprotic solvents. Steric effects on the base-catalysed step |
| title_full |
Aromatic nucleophilic substitutions with o- and p-fluoronitrobenzenes in aprotic solvents. Steric effects on the base-catalysed step |
| title_fullStr |
Aromatic nucleophilic substitutions with o- and p-fluoronitrobenzenes in aprotic solvents. Steric effects on the base-catalysed step |
| title_full_unstemmed |
Aromatic nucleophilic substitutions with o- and p-fluoronitrobenzenes in aprotic solvents. Steric effects on the base-catalysed step |
| title_sort |
aromatic nucleophilic substitutions with o- and p-fluoronitrobenzenes in aprotic solvents. steric effects on the base-catalysed step |
| publishDate |
1986 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1472779X_v_n5_p695_Nudelman http://hdl.handle.net/20.500.12110/paper_1472779X_v_n5_p695_Nudelman |
| work_keys_str_mv |
AT cerdeirasilviabeatriz aromaticnucleophilicsubstitutionswithoandpfluoronitrobenzenesinaproticsolventsstericeffectsonthebasecatalysedstep |
| _version_ |
1840321522419367936 |