Solvents effects on aromatic nucleophilic substitutions. Part 5. Kinetics of the reactions of 1-fluoro-2,4-dinitrobenzene with piperidine in aprotic solvents
The kinetics of the reaction between 1-fluoro-2,4-dinitrobenzene and piperidine were studied in toluene, benzene, dioxane, trichloroethane, tetrahydrofuran, chlorobenzene, ethyl acetate, chloroform, dichloromethane, acetone, acetonitrile, and nitromethane. The second-order rate coefficient is almost...
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1987
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| LEADER | 07024caa a22008177a 4500 | ||
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| 001 | PAPER-18062 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518204925.0 | ||
| 008 | 190411s1987 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-37049086082 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 100 | 1 | |a Nudelman, N.S. | |
| 245 | 1 | 0 | |a Solvents effects on aromatic nucleophilic substitutions. Part 5. Kinetics of the reactions of 1-fluoro-2,4-dinitrobenzene with piperidine in aprotic solvents |
| 260 | |c 1987 | ||
| 270 | 1 | 0 | |m Nudelman, N.S.; Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Mancini, P.M.E., Martinez, R.D., Vottero, L.R., Nudelman, N.S., (1986) J. Chem. Soc., Perkin Trans. 2, p. 1427. , Part 4 | ||
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| 520 | 3 | |a The kinetics of the reaction between 1-fluoro-2,4-dinitrobenzene and piperidine were studied in toluene, benzene, dioxane, trichloroethane, tetrahydrofuran, chlorobenzene, ethyl acetate, chloroform, dichloromethane, acetone, acetonitrile, and nitromethane. The second-order rate coefficient is almost insensitive to the amine concentration in chloroform, acetonitrile, and nitromethane; for the other solvents this value of k3/k2 is greater than 102, indicating neat base catalysis. The trend in k3/k2 does not follow the solvent basicity order; the solvents insensitive to base catalysis are those which exhibit hydrogen-bond donor (HBD) properties. These results are interpreted as an indication that in this reaction the detachment of the nucleofuge is the rate-limiting step in most of the aprotic solvents studied; those solvents which are H B D assist the departure of fluoride, and the formation of the intermediate is the rate-determining step. This conclusion was confirmed by kF/k Cl determinations. A simple linear energy solvation correlation was found between the parameter ET(30) and kA obtained at [B] < 10-2M. For higher amine contents increasing deviations were found. |l eng | |
| 593 | |a Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina | ||
| 593 | |a Inst. de Investigaciones de Productos Naturales, Análisis y Síntesis Orgánica, IPNAYS (CONICET-UNL-FIQ), 3000 Santa Fe, Argentina | ||
| 700 | 1 | |a Mancini, P.M.E. | |
| 700 | 1 | |a Martinez, R.D. | |
| 700 | 1 | |a Vottero, L.R. | |
| 773 | 0 | |d 1987 |h pp. 951-954 |k n. 8 |x 1472779X |t Journal of the Chemical Society, Perkin Transactions 2 | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-37049086082&partnerID=40&md5=a1fe3d68dd611dba6910c543ab8a1436 |y Registro en Scopus |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_1472779X_v_n8_p951_Nudelman |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1472779X_v_n8_p951_Nudelman |y Registro en la Biblioteca Digital |
| 961 | |a paper_1472779X_v_n8_p951_Nudelman |b paper |c PE | ||
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| 963 | |a VARI | ||
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