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Abstract:

The mechanism of aromatic nucleophilic substitutions by amines in protic solvents is well established; on the contrary the mechanism/s of the reactions in aprotic solvents is/are still subject of controversy. The present paper describes several systems for which fourth‐order kinetics (third‐order in amine) were observed. A mechanism is proposed to account for this as well as other observation such as: overall negative energies of activation, quadratic dependence of kA with non‐nucleophilic tertiary bases, spectacular effects of hydrogen‐bond donor (HBD) and hydrogen‐bond acceptor (HBA) catalysts, etc. Other alternative mechanisms are also discussed. Copyright © 1989 John Wiley & Sons Ltd.

Registro:

Documento: Artículo
Título:The ‘dimer mechanism’ in aromatic nucleophilic substitution by amines in aprotic solvents
Autor:Nudelman, N.S.
Filiación:Depto. Química Orgánica, Facultad de Ciencias Exactas y Naturales Universidad de Buenos Aires, P. 3, Cdad. Universitaria, Buenos Aires, 1428, Argentina
Año:1989
Volumen:2
Número:1
Página de inicio:1
Página de fin:14
DOI: http://dx.doi.org/10.1002/poc.610020102
Título revista:Journal of Physical Organic Chemistry
Título revista abreviado:J Phys Org Chem
ISSN:08943230
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_08943230_v2_n1_p1_Nudelman

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Citas:

---------- APA ----------
(1989) . The ‘dimer mechanism’ in aromatic nucleophilic substitution by amines in aprotic solvents. Journal of Physical Organic Chemistry, 2(1), 1-14.
http://dx.doi.org/10.1002/poc.610020102
---------- CHICAGO ----------
Nudelman, N.S. "The ‘dimer mechanism’ in aromatic nucleophilic substitution by amines in aprotic solvents" . Journal of Physical Organic Chemistry 2, no. 1 (1989) : 1-14.
http://dx.doi.org/10.1002/poc.610020102
---------- MLA ----------
Nudelman, N.S. "The ‘dimer mechanism’ in aromatic nucleophilic substitution by amines in aprotic solvents" . Journal of Physical Organic Chemistry, vol. 2, no. 1, 1989, pp. 1-14.
http://dx.doi.org/10.1002/poc.610020102
---------- VANCOUVER ----------
Nudelman, N.S. The ‘dimer mechanism’ in aromatic nucleophilic substitution by amines in aprotic solvents. J Phys Org Chem. 1989;2(1):1-14.
http://dx.doi.org/10.1002/poc.610020102