Who makes a better nucleophile? CH3O- or OH-? [duplicate]








**This question already has answers here**:
 
 




[Is methoxide a better nucleophile than hydroxide?](/questions/35068/is-methoxide-a-better-nucleophile-than-hydroxide)

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Closed 2 years ago.



My argument is that the +I effect of CH3 group increases the electron density at oxygen atom, making it a better nucleophile




When the donor atom is same, a general rule applies: nucleophilicity parallels basicity. Thus, comparing the basic strength of methoxide and hydroxide, it is observed that methoxide is a stronger base than hydroxide (as it the conjugate base of a weaker acid i.e. methanol when compared to water). Thus, methoxide is a stronger nucleophile than hydroxide.


[However, at the same time NMR data predicts that methanol is a stronger acid than water (despite the I+ effect of $\ce{-CH3}$ group)](https://chemistry.stackexchange.com/questions/42535/is-methanol-more-acidic-than-water). So, in this case, there exists a controversy.


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