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Topic: Sodium Cyanoborohydride stability in water  (Read 1012 times)

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Offline owk9688

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Sodium Cyanoborohydride stability in water
« 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?

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