[Nescafe]

Hello,

In the mechanism of Mitsonubu reaction DIAD acts as a base to deprotonate the nucleophile. My guess would be the Pka of DIAD would be anywhere between 13-15. I am not finding anything in literature. does anyone know?

EtOOC-N(-)-NH-COOEt

So the Pkah of the bolded nitrogen. There is some similarity to an amide (which has a Pka of 17) but since it is attached to an ester I predicted a Pka which is 100 times more acidic due to extended stabilization due to e withdrawing nature of the ester.

Thanks in advance,

Nescafe.

[Dan]

I don't know of any definitive source, but chemicalize.org estimates 11