Esr of organometallics

Gogan, Niall J.; Dickinson, Ian L.; Doull, James; Patterson, J. R.

doi:10.1016/s0022-328x(00)85527-8

Cited by 11 publications

(1 citation statement)

References 28 publications

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“…This is in agreement with the SCCC-MO results obtained for 3-benzoylpyrrole and its Cr(C0)3 complex (3) which indicated a small amount of upe on the pyrrole ring. It contrasts with the results obtained for substituted benzophenones and their complexes (13,14) which showed significant and observable upe on both of the Cr(C0)3 moiety. Substituents change vco (ketone) in the same direction for both ligand and complex suggesting that the orientation of the ketonic CO group with respect to the benzene ring is not significantly affected by complexation.…”

Section: Infrared and Nuclear Magnetic Resonance Studiescontrasting

confidence: 99%

Synthesis and spectroscopic studies of some substituted 3-benzoylpyrroles and their tricarbonylchromium complexes

Gogan¹,

McDonald²,

Anderson³

et al. 1989

Can. J. Chem.

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. Can. J. Chem. 67, 433 (1989).3-Benzoylpyrroles with a substituent on the pyrrole ring have been synthesized. Both the iodination and chlorination gave only the 2,4 derivatives while isopropylation gave mixtures of the 2,4 and 2,3 compounds. No 3,4 compounds were obtained. Both steric and electronic effects seem to determine the substitution pattern. The Cr(C0)3 complexes (Cr on the benzene ring) were prepared and these complexes, together with the uncomplexed pyrroles, were studied by IR, 'H-NMR, and ESR of the radical anions from the N-methylpyrrole derivatives. For the 2,4 compounds, the substituent on the pyrrole ring has relatively little effect on the spectral parameters of the benzene ring indicating relatively little electron delocalization between the two rings. 3-Benzoyl-2-isopropylpyrrole, however, gives an ESR spectrum very different from the other compounds.Key words: benzoylpyrroles, tricarbonylchromium, ESR, chlorination, isopropylpyrroles. On a synthCtis6 des benzoyl-3 pyrroles portant un substituant sur le noyau pyrrole. Leur iodation ainsi que leur chloration ne conduisent qu'aux dCrivCs 2,4 alors que la reaction d'isopropylation conduit i un melange des dtrivCs 2,4 ainsi que 2,3. On n'a pas obtenu de composCs substituCs en 3,4. I1 semble que des effets tant stCriques qu'Clectroniques soient responsables des patrons de substitution. On a prtpart des complexes du Cr(C0)3 (le Cr Ctant port6 par le noyau benzCnique) et on a dCterminC les spectres ir ainsi que les spectres rmn du 'H de ces complexes ainsi que des pyrroles non-substituCs; de plus, on a dCterminC les spectres rpe des radicaux anions obtenus i partir des dtrivts N-mCthylpyrroles. Dans les cas des composts 2,4, le substituant present sur le noyau pyrrole n'a pratiquement pas d'influence sur les paramktres spectraux du noyau benztnique; ces donntes sugggrent qu'il y a peu de dClocalisation Clectronique entre les deux noyaux. Toutefois, le benzoyl-3 isopropyl-2 pyrrole prCsente un spectre rpe qui est trks difftrent de celui des autres composts.

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Section: Infrared and Nuclear Magnetic Resonance Studiescontrasting

confidence: 99%