What is the Difference Between Electrofuge and Nucleofuge?

🆚 Go to Comparative Table 🆚

In chemistry, electrofuge and nucleofuge are terms used to describe leaving groups in reactions. The key difference between them lies in the way they interact with the bonding electrons during the reaction process:

  • Electrofuge: An electrophile does not retain the lone pair of electrons from its previous bond with another species. It can result from the heterolytic breaking of covalent bonds. After the reaction, an electrofuge may possess either a positive or a neutral charge, depending on the nature of the specific reaction. Examples of electrofuges include the loss of H+ from a molecule of benzene during nitration.
  • Nucleofuge: A nucleophile, on the other hand, retains the lone pair of electrons from its previous bond with another species. After a reaction, nucleofuges may contain either a negative or a neutral charge, depending on the nature of the specific reaction. An example of a nucleofuge is the bromo group in the SN2 mechanism, where a nucleophile attacks an organic compound containing the nucleofuge.

These terms were more commonly used in older literature, and their usage is less prevalent in modern chemistry literature.

Comparative Table: Electrofuge vs Nucleofuge

The main difference between electrofuge and nucleofuge lies in their bonding electron retention process. Here is a table comparing the two:

Property Electrofuge Nucleofuge
Definition Electrofuge compounds are leaving groups that do not retain the bonding pair of electrons. Nucleofuge compounds are leaving groups that do retain the bonding pair of electrons.
Charge Electrofuge groups tend to possess either a positive or a neutral charge, which is governed by the nature of the specific reaction. Nucleofuge groups tend to have either a negative charge or a neutral charge.
Examples An example of an electrofuge involving reaction is the loss of H+ ion from a molecule of benzene. An example of nucleofuge involves the SN2 mechanism where a nucleophile attacks and simultaneously breaks the bond with the nucleofuge.

These terms are used in organic chemistry and are related to leaving groups. However, it is essential to note that these terms were mainly used in older literature and are uncommon in modern chemistry literature.