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Electron-withdrawing groups exert an "inductive" or "electron-pulling" effect on covalent bonds. The strength of the electron-withdrawing group is inversely proportional to the pKa of the carboxylic acid. [2] The inductive effect is cumulative: trichloroacetic acid is 1000x stronger than chloroacetic acid.
With respect to acidity, a common trend to note is that, inductively, an electron-withdrawing substituent in the vicinity of an acidic proton will lower the pKa (i.e. increase the acidity) and, correspondingly, an electron-donating substituent will raise the pKa. [7] The reorganization of charge due to field effects will have the same result.
The negative charge that is left after deprotonation of the carboxyl group is delocalized between the two electronegative oxygen atoms in a resonance structure. If the R group is an electron-withdrawing group (such as –CF 3), the basicity of the carboxylate will be further weakened. [1]: 264–5
The value of pK a also depends on molecular structure of the acid in many ways. For example, Pauling proposed two rules: one for successive pK a of polyprotic acids (see Polyprotic acids below), and one to estimate the pK a of oxyacids based on the number of =O and −OH groups (see Factors that affect pK a values below).
The captodative effect is the stabilization of radicals by a synergistic effect of an electron-withdrawing substituent and an electron-donating substituent. [2] [3] The name originates as the electron-withdrawing group (EWG) is sometimes called the "captor" group, whilst the electron-donating group (EDG) is the "dative" substituent. [3]
In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula R−O−CH 3 . On a benzene ring , the Hammett equation classifies a methoxy substituent at the para position as an electron-donating group , but as an electron-withdrawing group if at the meta position.
compounds with a strong electron-withdrawing group attached to the acyl carbon (e.g. N,N-dimethyltrifluoroacetamide) [6] compounds with donor groups that are poorly conjugated with the potential carbonyl group (e.g. cyclol) [7] compounds with sulfur atoms bonded to the anomeric centre (e.g., S-acylated-1,8-naphthalenedithiol) [8]
In the reaction mechanism, there is 1 as the nucleophile: [3]. Deprotonation of 1 by a base leads to carbanion 2, stabilized by its electron-withdrawing groups.Structures 2a to 2c are three resonance structures that can be drawn for this species, two of which have enolate ions.