Please use this identifier to cite or link to this item:
Type: Artigo de periódico
Title: Marked Changes In Relative Nucleophilicity In Comparing Sn2ar Reactions Of Free Arenes And Coordinated Arenes. Kinetic Studies Of Reactions Of (η6-chlorobenzene) (η5-cyclopentadienyl)iron(ii) Tetrafluoroborate With Anionic And Neutral Nucleophiles
Author: Gomes P.C.B.
Vichi E.J.S.
Moran P.J.S.
Neto A.F.
Maroso M.L.
Miller J.
Abstract: Quantitative kinetic studies have been made of reactions of the (η6-chlorobenzene)(η5-cyclopentadienyl)iron(II) cation, (C6H5Cl)Fe(C5H5)+ (1), with methoxide, phenoxide, methanethiolate, benzenethiolate, and azide ions in methanol, piperidine, morpholine, aniline, and thiourea in methanol, and guanidine in ethanol. The results were compared with the same nucleophile-solvent combinations in reactions with 1-chloro-2,4-dinitrobenzene, C6H3(NO2)2Cl (2). In general, the reactivity decreases on passing from 2 to 1. The decrease is small (≤10-1) for phenoxide (PhO-), methanethiolate (MeS-), and guanidine (gua) and large (ca. 10-5) for benzenethiolate (PhS-), azide (N3 -), piperidine (pip), morpholine (morph), aniline (anil), and thiourea (thiou). The differences in reactivity when comparing the SN-2Ar reactions of 1 and 2 is discussed in terms of the different location of the negative charge generated in the transition state by the electrons displaced from the reaction center by the entering groups (arenide electrons).
Rights: fechado
Identifier DOI: 
Date Issue: 1996
Appears in Collections:Unicamp - Artigos e Outros Documentos

Files in This Item:
File Description SizeFormat 
2-s2.0-0000960096.pdf207.5 kBAdobe PDFView/Open

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.