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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1999
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n8_p1627_Nudelman http://hdl.handle.net/20.500.12110/paper_03009580_v_n8_p1627_Nudelman |
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paper:paper_03009580_v_n8_p1627_Nudelman2025-07-30T18:05:31Z 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. 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. 1999 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n8_p1627_Nudelman http://hdl.handle.net/20.500.12110/paper_03009580_v_n8_p1627_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 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. |
| title |
Reaction of 2,4-dinitrochlorobenzene with aniline. Solvent effects and molecular complex formation |
| spellingShingle |
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 |
| publishDate |
1999 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n8_p1627_Nudelman http://hdl.handle.net/20.500.12110/paper_03009580_v_n8_p1627_Nudelman |
| _version_ |
1840324572973367296 |