Decomposition of Inorganic and Organometallic Compounds: by C.H. Bamford and C.F.H. Tipper (Eds.)
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
58 A - S E ~o,r A2 with water as proton acceptor -0 Hf transfer to hydrocarbon bases ____ However, other examples are known in which the Bunnett criterion does not lead to the correct answer, either [go]. 6 . However, there is no doubt that the mechanism must be A l , and this is confirmed by the A V t  and ASf  values (see Tables 2 and 3). 3 which also apparently indicates an A2 mechanism  , though an A1 mechanism is more likely because of the expected steric hindrance. Actually, the AVf value observed by Withey and Whalley  supplies very strong evidence for an A 1 mechanism.
As carbon atoms with sp and sp2 configurations are more electronegative than sp3 carbon atoms, proton abstraction by bases from acetylenic, ethylenic, or aromatic CH bonds occurs more readily than from saturated aliphatic CH bonds. 5 . 3 THE RATE-DETERMINING STEP Usually, the proton transfer step in an acid-base catalyzed reaction is fast if it takes place between oxygen or nitrogen atoms. The reaction step may be slow and rate-determining if the proton is transferred either from or t o a carbon atom.
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. RC(OR+)X + R’OH FZZE RC(OH)(OR’H+)X F== RC(OH)(OR’H+)X RC(OH)(OR’)XH+ RC(OH)(OR’)XH+ G RC(OH)(OR’)+ + XH RC(OH)(OR’)+ + H,O RCOOR’ + H 3 0 + This is the general mechanism for acid catalyzed oxygen isotope exchange of carboxylic acids and esters, esterification, ester hydrolysis, and amide hydrolysis (see Vol.