Mayr's Database of Reactivity Parameters

benzaldehyde (in DMSO)

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Name benzaldehyde (in DMSO)
Molecule class Electrophiles » C-Electrophiles » Aldehydes
Molecular formula C7H6O
Quality *

E Param.: -12.90


Only 1 reference nucleophile was used to determine the E parameter. Determined from the kinetics of an epoxidation reaction with a carbanion (ArSO2CHCl-) and corrected by the splitting ratio of forward and backward reaction.

The previously reported E = -19.5 holds for the gross rate constant of the reversible attack of the S-ylide (4-NC-C6H4)CH=SMe2 at PhCHO (JACS 2011, 133, 8240), in which the epoxide ring closure is rate-determining.

Solvent DMSO
Reference J. Am. Chem. Soc. 2018, 140, 5500-5515