6533b7d8fe1ef96bd126b89e

RESEARCH PRODUCT

Experimental and theoretical study on the substitution reactions of aryl 2,4-dinitrophenyl carbonates with quinuclidines

Enrique A. CastroPaola R. CampodónicoJosé A. SáezRenato ContrerasJ. Ramón LeisPatricio FuentealbaJosé G. SantosLuis R. DomingoLuis García-río

subject

Substitution reactionReaction mechanismAqueous solutionArylOrganic ChemistryPhotochemistryBiochemistryIonchemistry.chemical_compoundchemistryNucleophileComputational chemistryDrug DiscoveryElectrophileDinitrophenyl

description

Abstract The reactions of quinuclidines with phenyl, 4-methylphenyl, and 4-chlorophenyl 2,4-dinitrophenyl carbonates are kinetically evaluated in aqueous solution. The Bronsted-type plots (log kN vs pKa of quinuclidinium ions) are linear. The magnitude of the slopes and validated theoretical scales of electrophilicity and nucleophilicity confirm the concerted nature of these reactions.

yearjournalcountryeditionlanguage
2006-01-01Tetrahedron
https://doi.org/10.1016/j.tet.2005.12.044