Stabilization of aliphatic and aromatic diazonium ions by coordination: An experimental and theoretical study
The reaction of [Ru(bpy)2(NO)Cl]2+ and [Fe(CN)5NO]2- with n-butylamine has been studied as a plausible route for obtaining aliphatic diazonium ions stabilized by coordination. These reactions yield a variety of products originating mainly by direct attack of nucleophiles on the intermediate carbocat...
Guardado en:
| Autores principales: | , , , , , |
|---|---|
| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_02767333_v19_n19_p3810_Doctorovich |
| Aporte de: |
| id |
todo:paper_02767333_v19_n19_p3810_Doctorovich |
|---|---|
| record_format |
dspace |
| spelling |
todo:paper_02767333_v19_n19_p3810_Doctorovich2023-10-03T15:15:59Z Stabilization of aliphatic and aromatic diazonium ions by coordination: An experimental and theoretical study Doctorovich, F. Escola, N. Trápani, C. Estrin, D.A. González Lebrero, M.C. Turjanski, A.G. Amines Complexation Coordination reactions Fourier transforms Ions Iron compounds Ruthenium compounds Aliphatic diazonium ions Carbocation Discrete Fourier transforms (DFT) Nucleophiles Aromatic compounds The reaction of [Ru(bpy)2(NO)Cl]2+ and [Fe(CN)5NO]2- with n-butylamine has been studied as a plausible route for obtaining aliphatic diazonium ions stabilized by coordination. These reactions yield a variety of products originating mainly by direct attack of nucleophiles on the intermediate carbocation (or diazonium ion) and by rearrangement of the carbocation or the diazonium ion. The ratio of unrearranged to rearranged products can be taken as an experimental measurement of the stabilization of the diazonium ions. DFT-computed results suggest that the stabilization by complexation of the diazonium ions is larger in the ironpentacyano complex, in agreement with the fact that no rearrangement products are observed in the reaction of this species with n-butylamine. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_02767333_v19_n19_p3810_Doctorovich |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Amines Complexation Coordination reactions Fourier transforms Ions Iron compounds Ruthenium compounds Aliphatic diazonium ions Carbocation Discrete Fourier transforms (DFT) Nucleophiles Aromatic compounds |
| spellingShingle |
Amines Complexation Coordination reactions Fourier transforms Ions Iron compounds Ruthenium compounds Aliphatic diazonium ions Carbocation Discrete Fourier transforms (DFT) Nucleophiles Aromatic compounds Doctorovich, F. Escola, N. Trápani, C. Estrin, D.A. González Lebrero, M.C. Turjanski, A.G. Stabilization of aliphatic and aromatic diazonium ions by coordination: An experimental and theoretical study |
| topic_facet |
Amines Complexation Coordination reactions Fourier transforms Ions Iron compounds Ruthenium compounds Aliphatic diazonium ions Carbocation Discrete Fourier transforms (DFT) Nucleophiles Aromatic compounds |
| description |
The reaction of [Ru(bpy)2(NO)Cl]2+ and [Fe(CN)5NO]2- with n-butylamine has been studied as a plausible route for obtaining aliphatic diazonium ions stabilized by coordination. These reactions yield a variety of products originating mainly by direct attack of nucleophiles on the intermediate carbocation (or diazonium ion) and by rearrangement of the carbocation or the diazonium ion. The ratio of unrearranged to rearranged products can be taken as an experimental measurement of the stabilization of the diazonium ions. DFT-computed results suggest that the stabilization by complexation of the diazonium ions is larger in the ironpentacyano complex, in agreement with the fact that no rearrangement products are observed in the reaction of this species with n-butylamine. |
| format |
JOUR |
| author |
Doctorovich, F. Escola, N. Trápani, C. Estrin, D.A. González Lebrero, M.C. Turjanski, A.G. |
| author_facet |
Doctorovich, F. Escola, N. Trápani, C. Estrin, D.A. González Lebrero, M.C. Turjanski, A.G. |
| author_sort |
Doctorovich, F. |
| title |
Stabilization of aliphatic and aromatic diazonium ions by coordination: An experimental and theoretical study |
| title_short |
Stabilization of aliphatic and aromatic diazonium ions by coordination: An experimental and theoretical study |
| title_full |
Stabilization of aliphatic and aromatic diazonium ions by coordination: An experimental and theoretical study |
| title_fullStr |
Stabilization of aliphatic and aromatic diazonium ions by coordination: An experimental and theoretical study |
| title_full_unstemmed |
Stabilization of aliphatic and aromatic diazonium ions by coordination: An experimental and theoretical study |
| title_sort |
stabilization of aliphatic and aromatic diazonium ions by coordination: an experimental and theoretical study |
| url |
http://hdl.handle.net/20.500.12110/paper_02767333_v19_n19_p3810_Doctorovich |
| work_keys_str_mv |
AT doctorovichf stabilizationofaliphaticandaromaticdiazoniumionsbycoordinationanexperimentalandtheoreticalstudy AT escolan stabilizationofaliphaticandaromaticdiazoniumionsbycoordinationanexperimentalandtheoreticalstudy AT trapanic stabilizationofaliphaticandaromaticdiazoniumionsbycoordinationanexperimentalandtheoreticalstudy AT estrinda stabilizationofaliphaticandaromaticdiazoniumionsbycoordinationanexperimentalandtheoreticalstudy AT gonzalezlebreromc stabilizationofaliphaticandaromaticdiazoniumionsbycoordinationanexperimentalandtheoreticalstudy AT turjanskiag stabilizationofaliphaticandaromaticdiazoniumionsbycoordinationanexperimentalandtheoreticalstudy |
| _version_ |
1807323354705690624 |