Nucleofuge

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A nucleofuge is a leaving group which retains the lone pair from its previous bond with another species. For example, in the SN2 mechanism a nucleophile attacks an organic compound containing the nucleofuge (the bromo group) which simultaneously breaks the bond with the nucleofuge.

SN2 reaction of bromoethane with hydroxide ion

After a reaction nucleofuges may contain either a negative or a neutral charge; this is governed by the nature of the specific reaction.

The word 'nucleofuge' is commonly found in older literature, but its use has been discontinued in current literature.

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