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...
Guardado en:
| Autores principales: | , |
|---|---|
| Formato: | JOUR |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_1472779X_v_n6_p805_Nudelman |
| Aporte de: |
| id |
todo:paper_1472779X_v_n6_p805_Nudelman |
|---|---|
| record_format |
dspace |
| spelling |
todo:paper_1472779X_v_n6_p805_Nudelman2023-10-03T16:18:03Z Theoretical calculations of chemical interactions. Part 4. Aromatic nucleophilic substitutions and SN2 reactions of 4- and 6-substituted 2-nitroanisoles Nudelman, N.S. Palleros, D.R. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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. |
| format |
JOUR |
| author |
Nudelman, N.S. Palleros, D.R. |
| spellingShingle |
Nudelman, N.S. Palleros, D.R. Theoretical calculations of chemical interactions. Part 4. Aromatic nucleophilic substitutions and SN2 reactions of 4- and 6-substituted 2-nitroanisoles |
| author_facet |
Nudelman, N.S. Palleros, D.R. |
| author_sort |
Nudelman, N.S. |
| title |
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 |
| url |
http://hdl.handle.net/20.500.12110/paper_1472779X_v_n6_p805_Nudelman |
| work_keys_str_mv |
AT nudelmanns theoreticalcalculationsofchemicalinteractionspart4aromaticnucleophilicsubstitutionsandsn2reactionsof4and6substituted2nitroanisoles AT pallerosdr theoreticalcalculationsofchemicalinteractionspart4aromaticnucleophilicsubstitutionsandsn2reactionsof4and6substituted2nitroanisoles |
| _version_ |
1807314552173363200 |