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

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...

Descripción completa

Guardado en:
Detalles Bibliográficos
Publicado: 1985
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1472779X_v_n6_p805_Nudelman
http://hdl.handle.net/20.500.12110/paper_1472779X_v_n6_p805_Nudelman
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_1472779X_v_n6_p805_Nudelman
record_format dspace
spelling paper:paper_1472779X_v_n6_p805_Nudelman2025-07-30T18:53:11Z Theoretical calculations of chemical interactions. Part 4. Aromatic nucleophilic substitutions and SN2 reactions of 4- and 6-substituted 2-nitroanisoles 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. 1985 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1472779X_v_n6_p805_Nudelman http://hdl.handle.net/20.500.12110/paper_1472779X_v_n6_p805_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 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.
title Theoretical calculations of chemical interactions. Part 4. Aromatic nucleophilic substitutions and SN2 reactions of 4- and 6-substituted 2-nitroanisoles
spellingShingle Theoretical calculations of chemical interactions. Part 4. Aromatic nucleophilic substitutions and SN2 reactions of 4- and 6-substituted 2-nitroanisoles
title_short Theoretical calculations of chemical interactions. Part 4. Aromatic nucleophilic substitutions and SN2 reactions of 4- and 6-substituted 2-nitroanisoles
title_full Theoretical calculations of chemical interactions. Part 4. Aromatic nucleophilic substitutions and SN2 reactions of 4- and 6-substituted 2-nitroanisoles
title_fullStr Theoretical calculations of chemical interactions. Part 4. Aromatic nucleophilic substitutions and SN2 reactions of 4- and 6-substituted 2-nitroanisoles
title_full_unstemmed Theoretical calculations of chemical interactions. Part 4. Aromatic nucleophilic substitutions and SN2 reactions of 4- and 6-substituted 2-nitroanisoles
title_sort theoretical calculations of chemical interactions. part 4. aromatic nucleophilic substitutions and sn2 reactions of 4- and 6-substituted 2-nitroanisoles
publishDate 1985
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1472779X_v_n6_p805_Nudelman
http://hdl.handle.net/20.500.12110/paper_1472779X_v_n6_p805_Nudelman
_version_ 1840323676238512128

Ejemplares similares