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EnglishThe kinetics of the iso-heterocyclic mononuclear rearrangement of some 3-aroylamino-5-methyl-1,2,4-ozadiazoles was carefully examined under largely variable acidic or alkaline conditions. This reaction may proceed via two different mechanistic pathways (an uncatalyzed and a base-catalyzed one), as accounted for also by evaluation of the relevant activation parameters. Substituent effects, as quantified by means of Hammett's equation, appear relatively modest; however, they reveal some interesting anomalies, which enabled us to draw a very precise picture of the intimate reaction course.
Frenna, V., Lo Meo, P., Palumbo Piccionello, A., & Spinelli, D. (2019). Unexpected Substituent Effects in the Iso-Heterocyclic Boulton-Katritzky Rearrangement of 3-Aroylamino-5-Methyl-1,2,4-Oxadiazoles: a Mechanistic Study. JOURNAL OF PHYSICAL CHEMISTRY. A, MOLECULES, SPECTROSCOPY, KINETICS, ENVIRONMENT, & GENERAL THEORY, 123, 10004-10010.
| Data di pubblicazione: | 2019 |
| Titolo: | Unexpected Substituent Effects in the Iso-Heterocyclic Boulton-Katritzky Rearrangement of 3-Aroylamino-5-Methyl-1,2,4-Oxadiazoles: a Mechanistic Study |
| Autori: | SPINELLI, Domenico (Corresponding) |
| Citazione: | Frenna, V., Lo Meo, P., Palumbo Piccionello, A., & Spinelli, D. (2019). Unexpected Substituent Effects in the Iso-Heterocyclic Boulton-Katritzky Rearrangement of 3-Aroylamino-5-Methyl-1,2,4-Oxadiazoles: a Mechanistic Study. JOURNAL OF PHYSICAL CHEMISTRY. A, MOLECULES, SPECTROSCOPY, KINETICS, ENVIRONMENT, & GENERAL THEORY, 123, 10004-10010. |
| Rivista: | |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1021/acs.jpca.9b08675 |
| Abstract: | The kinetics of the iso-heterocyclic mononuclear rearrangement of some 3-aroylamino-5-methyl-1,2,4-ozadiazoles was carefully examined under largely variable acidic or alkaline conditions. This reaction may proceed via two different mechanistic pathways (an uncatalyzed and a base-catalyzed one), as accounted for also by evaluation of the relevant activation parameters. Substituent effects, as quantified by means of Hammett's equation, appear relatively modest; however, they reveal some interesting anomalies, which enabled us to draw a very precise picture of the intimate reaction course. |
| Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
| Appare nelle tipologie: | 1.01 Articolo in rivista |
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