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- W1602022108 abstract "In order to obtain information on the electronic transmission of polar substituent effects in biarylic systems, a kinetic study of the piperidino-debromination reactions of some 3′-. 4′-substituted 3-nitro-4-bromobiphenyls (substituents = H, Hal, CH3CO, SO2CH3, NO2) in methanol has been carried out. A good fit to the Hammett equation was found with ϱ = + 1·00. The experimental data obtained show that the polar effects of 3′-substituents and 4′-Hal in the reactions studied are similar to the ones exerted by the same substituents in the 5- and 4-positions respectively in the piperidino-debromination reaction of o-nitrobromobenzene. For the strongly electron withdrawing 4′-substituents (COCH3, SO2CH3, NO2) we found it necessary to use values [σp + 0·32 (σ− - σp] for the substituent constants. This result is consistent with a lower contribution of extraconjugative effects to the total polar effect for the 4′-substituents with respect to that reported for the para-substituents in nucleophilic substitution reactions on benzenic derivatives." @default.
- W1602022108 created "2016-06-24" @default.
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- W1602022108 date "1971-01-01" @default.
- W1602022108 modified "2023-09-26" @default.
- W1602022108 title "Biphenyl series—II" @default.
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- W1602022108 doi "https://doi.org/10.1016/s0040-4020(01)98045-7" @default.
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