0000000000172094

AUTHOR

Gabriele Micheletti

0000-0001-9746-2356

showing 2 related works from this author

Mononuclear Rearrangement of the Z-Phenylhydrazones of Some 3-Acyl-1,2,4-oxadiazoles: Effect of Substituents on the Nucleophilic Character of the &gt…

2019

The reaction rates for the mononuclear rearrangement of the Z-phenylhydrazones of 3-acyl-1,2,4-oxadiazoles 3a-c into the relevant 2-phenyl-2 H-1,2,3-triazoles (4a-c) have been measured in dioxane/water at different temperatures in a large range of proton concentrations. The occurrence of two different reaction pathways (one uncatalyzed, water assisted, and the other general base catalyzed) has- been observed. The obtained results have been able to furnish information about the effects of the nature of the 3-acyl structure and of the 5-substituents in the 1,2,4-oxadiazole ring on the reactivity of the examined rearrangements: they are well in line with the previsions carried out considering …

010405 organic chemistryChemistryOrganic ChemistryOxadiazoleCharge density010402 general chemistryRing (chemistry)01 natural sciencesMedicinal chemistry0104 chemical sciencesCatalysisReaction ratechemistry.chemical_compoundNucleophileElectrophileReactivity (chemistry)The Journal of Organic Chemistry
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On the Nucleophilic Reactivity of 4,6-Dichloro-5-nitrobenzofuroxan with Some Aliphatic and Aromatic Amines: Selective nucleophilic substitution

2020

The reaction rates for the nucleophilic aromatic substitution of 4,6-dichloro-5-nitrobenzofuroxan 1 with eight aliphatic amines (characterized by very different basicities/ nucleophilicities) and three anilines have been measured in both methanol and toluene. The obtained rates have been related to the basicity (pKaH in water and Kb in benzene) or nucleophilicity (N Mayr constants) of the tested amines. The whole of the obtained kinetic data has furnished useful information on the high nucleophilic reactivity of benzofuroxan derivatives, which has been related essentially to two factors: the high electron-drawing ability/power of the condensed furoxan ring and the low aromatic character of …

KineticOrganic ChemistryFuroxanBenzofuroxanTolueneMedicinal chemistrySNArchemistry.chemical_compoundchemistryNucleophileNucleophilic aromatic substitutionAromaticity IndexNucleophilic substitutionMayr constantReactivity (chemistry)MethanolBenzene
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