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For questions involving the nucleophilicity of a chemical species. Not to be confused with "basicity", use the [acid-base] tag instead.

6 votes

Is hydrazine a better nucleophile than ammonia?

A quantitative approach may be found in the Mayr nucleophilicity parameters (Ctrl-F "ammonia" and "hydrazine"): $$\begin{array}{ccc} \hline \text{Nucleophile} & N\text{ parameter in }\ce{H2O} & N\text … It also makes sense that the protic solvent water reduces the nucleophilicity of both species. For more details I suggest reading the articles cited in the database entries. …
orthocresol's user avatar
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5 votes
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Effects of Groups on the Nucleophilcity of Nitrogen

Your analysis of "pulls more electron density away" is a bit too simplistic. Both of them are approximately equally electron-withdrawing via the inductive effect, but in terms of resonance, which is t …
orthocresol's user avatar
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