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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: owk9688 on December 09, 2020, 05:21:37 PM

Title: Sodium Cyanoborohydride stability in water
Post by: owk9688 on December 09, 2020, 05:21:37 PM

Hello,

I'm confused about why Sodium Cyanoborohydride is stable in water. Initially I thought it was simply because the electron withdrawing cyano ligand reduces the basicity on the hydrides enough to not allow them to react with water on a reasonable timescale. But, I recently discovered that Sodium triacetoxyborohydride, which is far less nucleophilic (the three acetate ligands are way more withdrawing than a single cyano ligand...right?), reacts readily with water, so my reasoning seems to not be true. Does anyone know what makes NaBH₃CN seemingly uniquely stable in protic solvents?