Reactive Intermediate Chemistry

REACTIVITY 111

minimum and is formed without crossing a barrier), but in acyl substitutions on other substrates, such as acid chlorides, Brauman has shown that the tetrahedral

species can be an energy maximum (i.e., transition state) on the potential energy surface.192,193 With CF3 , an addition product is formed, but it does not continue

with the substitution process.194 The difference in reactivity between the two anions can be understood from the thermodynamics of the reactions. The cyanoacetone that is formed in the reaction with CH2C N is expected to be very acidic given that ketones are reasonably acidic in the gas phase and cyano is a powerful acidifying group. The enhanced acidity allows the overall substitution–methanal expulsion process to be exothermic. With CF3 , the resulting ketone, MeC(O)CF3, is not quite acidic enough to allow for an exothermic substitution process. Of course, it is more acidic than MeOH in the gas phase (i.e., MeO can deprotonate it), but not by enough to overcome the inherent endothermicity of the conversion of an ester to a ketone. With both nucleophiles, proton transfer also occurs and produces the ester enolate of methyl acetate.

Scheme 3.15

When CF3 is allowed to react with methyl benzoate, a new reaction channel appears along with the formation of the carbonyl addition product (Eq. 25).194 The nucleophile attacks at the methyl group to give an SN2 substitution with the formation of the benzoate ion. In this case, proton transfer is not possible (no a hydrogens), but benzoate is a better leaving group than acetate and substitution at the methyl group becomes viable.

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