Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation
The kinetics of the reaction of aniline with 2,4-dinitrochlorobenzene (2,4-DNC1B) were studied in several benzene-n-hexane mixtures at 40 °C in the presence of variable amounts of aniline. A linear dependence of the second-order rate coefficients, kA, with [B] is observed, with a null intercept. Tak...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_03009580_v_n8_p1627_Nudelman |
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todo:paper_03009580_v_n8_p1627_Nudelman2023-10-03T15:18:07Z Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation Nudelman, N.S. Savini, M. Alvaro, C.E.S. Nicotra, V. Yankelevich, J. The kinetics of the reaction of aniline with 2,4-dinitrochlorobenzene (2,4-DNC1B) were studied in several benzene-n-hexane mixtures at 40 °C in the presence of variable amounts of aniline. A linear dependence of the second-order rate coefficients, kA, with [B] is observed, with a null intercept. Taking into account the non-polar character of the solvent, and the excellent nucleofugacity of chlorine, this kinetic behaviour is interpreted as evidence of the aggregation of aniline, the hydrogen-bonded dimer acting as the nucleophile. Consistent with this interpretation, when the solvent is changed to THF, a good hydrogen-bond acceptor (HBA), the kA is no longer dependent on [B]. Electron donor-acceptor (EDA) molecular complexes of 2,4-DNC1B with benzene and with aniline, and also between aniline and the product, were clearly recognized and the stability constants of each one of these complexes were determined. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_03009580_v_n8_p1627_Nudelman |
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Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| description |
The kinetics of the reaction of aniline with 2,4-dinitrochlorobenzene (2,4-DNC1B) were studied in several benzene-n-hexane mixtures at 40 °C in the presence of variable amounts of aniline. A linear dependence of the second-order rate coefficients, kA, with [B] is observed, with a null intercept. Taking into account the non-polar character of the solvent, and the excellent nucleofugacity of chlorine, this kinetic behaviour is interpreted as evidence of the aggregation of aniline, the hydrogen-bonded dimer acting as the nucleophile. Consistent with this interpretation, when the solvent is changed to THF, a good hydrogen-bond acceptor (HBA), the kA is no longer dependent on [B]. Electron donor-acceptor (EDA) molecular complexes of 2,4-DNC1B with benzene and with aniline, and also between aniline and the product, were clearly recognized and the stability constants of each one of these complexes were determined. |
| format |
JOUR |
| author |
Nudelman, N.S. Savini, M. Alvaro, C.E.S. Nicotra, V. Yankelevich, J. |
| spellingShingle |
Nudelman, N.S. Savini, M. Alvaro, C.E.S. Nicotra, V. Yankelevich, J. Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation |
| author_facet |
Nudelman, N.S. Savini, M. Alvaro, C.E.S. Nicotra, V. Yankelevich, J. |
| author_sort |
Nudelman, N.S. |
| title |
Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation |
| title_short |
Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation |
| title_full |
Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation |
| title_fullStr |
Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation |
| title_full_unstemmed |
Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation |
| title_sort |
reaction of 2,4-dinitrochlorobenzene with aniline. solvent effects and molecular complex formation |
| url |
http://hdl.handle.net/20.500.12110/paper_03009580_v_n8_p1627_Nudelman |
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