Chemo-selective hydrolysis of the iminic moiety in salicylaldehyde semicarbazone promoted by ruthenium
| Autor: | Hugo Cerecetto, Mercedes González, Lucía Otero, Marisol Vieites, Eliezer J. Barreiro, Oscar E. Piro, Pablo Buccino, Carlos Mauricio R. Sant’ Anna, Roberto Delgado, Dinorah Gambino |
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| Rok vydání: | 2005 |
| Předmět: |
chemistry.chemical_classification
Semicarbazide Double bond chemistry.chemical_element Medicinal chemistry Tautomer Ruthenium Inorganic Chemistry Benzaldehyde chemistry.chemical_compound chemistry Salicylaldehyde Materials Chemistry Organic chemistry Moiety Physical and Theoretical Chemistry Semicarbazone |
| Zdroj: | Inorganica Chimica Acta. 358:3065-3074 |
| ISSN: | 0020-1693 |
| Popis: | ortho -Hydroxybenzaldehyde semicarbazone (salicylaldehyde semicarbazone) undergoes chemo-selective hydrolysis of the iminic carbon nitrogen double bond through its reaction with [RuCl 2 (dmso) 4 ] in ethanol in the presence of water, yielding free salicylaldehyde and semicarbazide that remains coordinated to the ruthenium ion as a bidentate N,O-donor to afford [RuCl 2 (dmso) 2 (semicarbazide)] · 2H 2 O complex. The ruthenium–semicarbazide complex has been characterized by 1 H NMR and FTIR spectroscopies and X-ray diffraction methods. Related semicarbazones, derived from p -hydroxybenzaldehyde and benzaldehyde, were not hydrolyzed under the same conditions, suggesting a significant role of the structural o -hydroxy motive in the reaction. Theoretical studies were performed in order to gain further insight on the mechanism of reaction. Results support the hypothesis that the ortho -hydroxy moiety, in the keto tautomeric form, participates in the chemo-selective hydrolysis promoted by [RuCl 2 (dmso) 4 ]. |
| Databáze: | OpenAIRE |
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