![]() The immediate product is, if anything, more interesting than the transition state with quite a stretched length for the newly formed C-H bond and predicted stretching wavenumber for this bond of 2137 cm -1. The free energy barrier is 9.6 kcal/mol (ωB97XD/6-311+G(d,p)/SCRF=water) which corresponds to a very fast reaction at room temperatures. In this model, we will assume that the carbonyl has not first reacted with water to form a gem-diol. First, n=2, for which the IRC is shown below. Initially, I am using Li, not Na (X=Li), to enable a more or less equal comparison with LAH, with water molecules to solvate rather than ether (n=2,3,5) and R set to Me. Here I start an exploration of why it is such a different reducing agent. reduce aldehydes and ketones, but it leaves acids, amides and esters alone. Sodium borohydride is the tamer cousin of lithium aluminium hydride (LAH).
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