Monday, January 7, 2019

organic chemistry - Is hydronium an electrophile, nucleophile, both or neither?


Is hydronium an electrophile or a nucleophile? I expected HX3OX+ to be a nucleophile due to the presence of electrons in the 2p orbitals of O. But the answer key of the test states that its none of them.


I can rationalise it this way: If O donates its 2 electrons then there would be 2 positive charges on O leading to instability.


But I am not too sure of my reasoning either. Isn't hydronium serving as a nucleophile in its reaction with OHX ? Why is it then neither an electrophile nor a nucleophile?


Google books results show that its mentioned as an electrophile in some books. While there's disagreement on other sides on the internet? What's the true classification?





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