By C.H. Bamford and C.F.H. Tipper (Eds.)
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Extra info for Decomposition of Inorganic and Organometallic Compounds: Homogeneous Decompostion of Hydrides, Decompostion of Inorganic Oxides and Sulphides; Halides and Derivatives; Metal Alkyls, Aryls, Carbonyls and Nitrosyls
Protonation of a carbonyl oxygen atom facilitates addition of a nucleophile to the carbonyl carbon in the next step, viz. + R 2 C = 0 + H,O+ R2COH++ Nu - R2COH+ + H,O R2C(OH)Nu There are many examples of acid catalyzed carbonyl addition reactions, such as formation of hydrates (R, C(OH), ), hemiacetals, hemiketals, cyanohydrins, bisulfite compounds, azomethines, oximes, hydrazones, etc. These important reactions are discussed in Vol. 11. If the substrate is a carboxylic acid, ester, or amide, addition of the nucleophile R’O- or R’OH (R’ = H or alkyl) to the intermediate in the first step is followed by elimination of the other nucleophile X (= OR”, OH, or NR; ) in one of the subsequent steps, viz.
33) and (35). and n,,, Results are collected in Table 7. In the next step, values of pi referring to HA bonds have been calculated from experimental A G t values for reactions of the type RH+A- - R-+HA utilizing known pi values for RH bonds. 09 (Table 7), with the exception of two reactions involving nitromethane, with lower p 2 values. This indicates that proton transfer between these oxygen bases must be fast as expected. )It follows that the assumption of the constancy of the pi values is essentially correct for these examples.
Therefore, it may be expected that pi increases with increasing importance of resonance in the carbanion. A more theoretical model of the energy barrier of proton transfer reactions has been introduced by Marcus [ 1331 . This simple semiempirical model is, to some extent, related t o Marcus' model. It is assumed that the p 1 value referring to the ionic cleavage in water of an XH bond remains unchanged in transition states with different groups Y, and correspondingly, the value of p 2 referring t o a YH bond does not depend on the particular X group in the transition state.
Decomposition of Inorganic and Organometallic Compounds: Homogeneous Decompostion of Hydrides, Decompostion of Inorganic Oxides and Sulphides; Halides and Derivatives; Metal Alkyls, Aryls, Carbonyls and Nitrosyls by C.H. Bamford and C.F.H. Tipper (Eds.)