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W2108527311 abstract "Abstract 13 C NMR spectra of 37 ortho ‐, meta ‐, and para ‐substituted phenyl benzoates, containing substituents in benzoyl and phenyl moiety, 4 ortho ‐substituted methyl and 5 ethyl benzoates as well as 9 R‐substituted alkyl benzoates have been recorded. The influence of the ortho substituents on the carbonyl carbon 13 C NMR chemical shift, δ CO , was found to be described by a linear multiple regression equation containing the inductive, σ I , resonance, σ ° R , and steric, E , or υ substituent constants. For all the ortho ‐substituted esters containing substituents in the acyl part as well as the phenyl part, the substituent‐induced reverse inductive effect ( ρ I < 0), the normal resonance effect ( ρ R > 0), and the negative steric effect ( δ ortho < 0) with the E were observed. In the case of ortho substituents in the phenyl part, the resonance effect was negligible. Due to inductive effect, the ortho electron‐withdrawing substituents showed an upfield shift or shielding of the carbonyl carbon, while the electron‐donating substituents had an opposite effect. Because of the sterical consequences, ortho substituents revealed a deshielding effect on the 13 C NMR chemical shift of the carbonyl carbon. For all the meta‐ and para‐ substituted esters, the reverse substituent‐induced inductive and resonance effects ( ρ I < 0, ρ R < 0) were found to be significant. In alkyl benzoates, the alkyl substituents showed the reverse inductive and steric effects. The log k values for the alkaline hydrolysis in water, aqueous 0.5 M Bu 4 NBr and 2.25 M Bu 4 NBr, and the IR frequencies, ν CO , for the ortho ‐, meta ‐, and para ‐substituted phenyl benzoates and alkyl benzoates were correlated nicely with the corresponding 13 C NMR substituent chemical shifts, Δ δ CO . Copyright © 2009 John Wiley & Sons, Ltd." @default.
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W2108527311 date "2009-06-29" @default.
W2108527311 modified "2023-10-17" @default.
W2108527311 title "Effect of <i>ortho</i> substituents on carbonyl carbon <sup>13</sup>C NMR chemical shifts in substituted phenyl benzoates" @default.
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W2108527311 doi "https://doi.org/10.1002/poc.1569" @default.
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