Theoretical calculations of chemical interactions. Part 4. Aromatic nucleophilic substitutions and SN2 reactions of 4- and 6-substituted 2-nitroanisoles

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The reactions of 4-R- and 6-R-2-nitroanisoles (R = Me, Br) in neat cyclohexylamine and piperidine have been studied. The reactions with cyclohexylamine lead to the respective aromatic nucleophilic substitution products while the reactions with piperidine mainly yield the substituted nitrophenols. It...

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Detalles Bibliográficos
Autor principal: Nudelman, N.S
Otros Autores: Palleros, D.R
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 1985
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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100 1 |a Nudelman, N.S. 
245 1 0 |a Theoretical calculations of chemical interactions. Part 4. Aromatic nucleophilic substitutions and SN2 reactions of 4- and 6-substituted 2-nitroanisoles 
260 |c 1985 
270 1 0 |m Nudelman, N.S.; Departmento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
506 |2 openaire  |e Política editorial 
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504 |a Calculations were performed on an IBM 370 Computer. Programs were obtained from the Quantum Chemical Program Exchange, Indiana University, Bloomington, Ind. 7401, U.S; Nudelman, N.S., Palleros, D., (1981) J. Chem. Soc., Perkin Trans. 2, p. 995 
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520 3 |a The reactions of 4-R- and 6-R-2-nitroanisoles (R = Me, Br) in neat cyclohexylamine and piperidine have been studied. The reactions with cyclohexylamine lead to the respective aromatic nucleophilic substitution products while the reactions with piperidine mainly yield the substituted nitrophenols. It was found that 6-R-2-nitroanisoles react faster than the respective 4-R-2-nitroanisoles. The absence of the expected primary steric effect is thought to be due to the spatial arrangement of the methoxide group, which adopts a conformation perpendicular to the ring plane when it is surrounded by two ortho-substituents. CNDO and INDO calculations for different conformations of the substrates give support to this assumption.  |l eng 
593 |a Departmento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
593 |a Scientific Research Career of the National Research Council (CONICET), Argentina 
700 1 |a Palleros, D.R. 
773 0 |d 1985  |h pp. 805-809  |k n. 6  |x 1472779X  |t Journal of the Chemical Society, Perkin Transactions 2 
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999 |c 79163 

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