The presence of a correlation between the basicity with respect to hydrogen of carbanions of nitrocompounds and their basicity with respect to carbon in the reaction series of acetaldehyde and formaldehyde was demonstrated.
The basicity of carbanions with respect to carbon in the series of acetaldehyde is two orders of magnitude less than the basicity of the same carbanions in the series of formaldehyde. This phenomenon was explained from the standpoint of differences in the steric stress in the molecules of the nitroalcohols formed by condensation of the nitro-compounds with acetaldehyde and formaldehyde.
The nucleophilicity of anions of nitro-compounds with respect to carbon varies correspondingly to the nucleophilicity of these anions with respect to hydrogen.
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Belikov, V.M., Belokon', Y.N., Martinkova, N.S. et al. Relationship between the reactivity of aliphatic nitro-compounds in protolytic reactions and reactions op nucleophilic addition to the carbonyl group. Russ Chem Bull 18, 1992–1996 (1969). https://doi.org/10.1007/BF00906608
- Carbonyl Group