6533b7ddfe1ef96bd1273613
RESEARCH PRODUCT
On the Nucleophilic Reactivity of 4,6-Dichloro-5-nitrobenzofuroxan with Some Aliphatic and Aromatic Amines: Selective nucleophilic substitution
Alexander R. BurilovDomenico SpinelliCarla BogaVincenzo FrennaGabriele MichelettiNurgali AkylbekovGiovanni ConsiglioElena Chugunovasubject
KineticOrganic ChemistryFuroxanBenzofuroxanTolueneMedicinal chemistrySNArchemistry.chemical_compoundchemistryNucleophileNucleophilic aromatic substitutionAromaticity IndexNucleophilic substitutionMayr constantReactivity (chemistry)MethanolBenzenedescription
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 the benzofuroxan system.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2020-11-06 |