Leaving group effects on the mechanism of aromatic nucleophilic substitution (SNAr) reactions of some phenyl 2,4,6‐trinitrophenyl ethers with aniline in acetonitrile

dc.contributor.authorCrampton, M. R.
dc.contributor.authorEmokpae, T. A.
dc.contributor.authorHoward, J. A.
dc.contributor.authorIsanbor, C.
dc.contributor.authorMondal, R.
dc.date.accessioned2019-08-23T14:30:27Z
dc.date.available2019-08-23T14:30:27Z
dc.date.issued2003-11-14
dc.description.abstractKinetic studies are reported for the reactions with aniline in acetonitrile of a series of X‐phenyl 2,4,6‐trinitrophenyl ethers [X=H, 2‐, 3‐, 4‐CH3, 2,4‐, 2,6‐(CH3)2, 2‐, 3‐, 4‐NO2, 2,4‐, 2,6‐(NO2)2]. X‐ray crystal structures for X=H, 2,6‐(CH3)2 and 2,6‐(NO2)2 are reported and provide evidence for steric crowding around the 1‐position of these molecules. Nevertheless, the kinetic data show that increasing substitution does not sterically inhibit nucleophilic attack by aniline and an ‘early’ transition state is likely. In general, the reactions are base catalysed; interpreted as rate‐limiting deprotonation of the zwitterionic intermediates. Only with the dinitro derivatives is an uncatalysed reaction involving intramolecular proton transfer observed and when X=2,6‐(NO2)2 this pathway takes all the reaction flux.en_US
dc.identifier.citationCrampton, M. R., Emokpae, T. A., Howard, J. A., Isanbor, C., & Mondal, R. (2004). Leaving group effects on the mechanism of aromatic nucleophilic substitution (SNAr) reactions of some phenyl 2, 4, 6‐trinitrophenyl ethers with aniline in acetonitrile. Journal of physical organic chemistry, 17(1), 65-70.en_US
dc.identifier.urihttps://ir.unilag.edu.ng/handle/123456789/4630
dc.language.isoen_USen_US
dc.publisherWileyen_US
dc.subjectResearch Subject Categories::NATURAL SCIENCES::Chemistry::Physical chemistry::Kineticsen_US
dc.subjectLeaving group effectsen_US
dc.subjectanilineen_US
dc.subjectcrystal structuresen_US
dc.subjectnucleophilic aromatic substitutionen_US
dc.subjectphenyl-2,4,6-trinitrophenyl etheren_US
dc.titleLeaving group effects on the mechanism of aromatic nucleophilic substitution (SNAr) reactions of some phenyl 2,4,6‐trinitrophenyl ethers with aniline in acetonitrileen_US
dc.typeArticleen_US
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