Unexpected Substituent Effects in the Iso-Heterocyclic Boulton-Katritzky Rearrangement of 3-Aroylamino-5-Methyl-1,2,4-Oxadiazoles: a Mechanistic Study

Paolo Maria Giuseppe Lo Meo; Antonio Palumbo Piccionello; Vincenzo Frenna; Domenico Spinelli; Domenico Spinelli

Unexpected Substituent Effects in the Iso-Heterocyclic Boulton-Katritzky Rearrangement of 3-Aroylamino-5-Methyl-1,2,4-Oxadiazoles: a Mechanistic Study

Paolo Maria Giuseppe Lo Meo, Antonio Palumbo Piccionello, Vincenzo Frenna, Domenico Spinelli, Domenico Spinelli

Scienze e Tecnologie Biologiche Chimiche e Farmaceutiche

Risultato della ricerca: Article › peer review

1 Citazioni (Scopus)

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.

Lingua originale	English
pagine (da-a)	10004-10010
Numero di pagine	7
Rivista	JOURNAL OF PHYSICAL CHEMISTRY. A, MOLECULES, SPECTROSCOPY, KINETICS, ENVIRONMENT, & GENERAL THEORY
Volume	123
Stato di pubblicazione	Published - 2019

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry

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Unexpected Substituent Effects in the Iso-Heterocyclic Boulton-Katritzky Rearrangement of 3-Aroylamino-5-Methyl-1,2,4-Oxadiazoles: a Mechanistic Study. / Lo Meo, Paolo Maria Giuseppe ; Palumbo Piccionello, Antonio ; Frenna, Vincenzo; Spinelli, Domenico; Spinelli, Domenico.

In: JOURNAL OF PHYSICAL CHEMISTRY. A, MOLECULES, SPECTROSCOPY, KINETICS, ENVIRONMENT, & GENERAL THEORY, Vol. 123, 2019, pag. 10004-10010.

Risultato della ricerca: Article › peer review

Lo Meo, Paolo Maria Giuseppe ; Palumbo Piccionello, Antonio ; Frenna, Vincenzo ; Spinelli, Domenico ; Spinelli, Domenico. / Unexpected Substituent Effects in the Iso-Heterocyclic Boulton-Katritzky Rearrangement of 3-Aroylamino-5-Methyl-1,2,4-Oxadiazoles: a Mechanistic Study. In: JOURNAL OF PHYSICAL CHEMISTRY. A, MOLECULES, SPECTROSCOPY, KINETICS, ENVIRONMENT, & GENERAL THEORY. 2019 ; Vol. 123. pagg. 10004-10010.

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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.",

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AU - Palumbo Piccionello, Antonio

AU - Frenna, Vincenzo

AU - Spinelli, Domenico

PY - 2019

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N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10447/382178

M3 - Article

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SP - 10004

EP - 10010

JO - JOURNAL OF PHYSICAL CHEMISTRY. A, MOLECULES, SPECTROSCOPY, KINETICS, ENVIRONMENT, & GENERAL THEORY

JF - JOURNAL OF PHYSICAL CHEMISTRY. A, MOLECULES, SPECTROSCOPY, KINETICS, ENVIRONMENT, & GENERAL THEORY

SN - 1089-5639

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