Chemistry

Difference Between Electrophile and Nucleophile

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Main Difference

The main difference between Electrophile and Nucleophile is that Electrophile is known as a molecule that can receive pairs of the electron, whereas Nucleophile is known as a molecule or atom that can give a pair of electrons.

Electrophile vs. Nucleophile

An Electrophile is considered as a molecule or atom that can readily receive an electron pair mainly from the electron-rich atom, ion, or molecule. On the other hand, the Nucleophile is considered as an ion, a molecule, or an atom that contains a high density of electrons and preferably donates pair of electrons. After accepting a pair of the electron, Electrophile produces a covalent bond, a Nucleophile in its comparison, donates a lone pair to produce a covalent bond.

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Either positively charged or neutrally charged, Electrophile is present; on the contrary, either negatively charged or neutrally charged Nucleophile is present. The Electrophile can be identified by formal positive charge, a partial positive charge, and a neutral ion, atom, or molecule, which does not obey the octet rule. In contrast, the Nucleophile is identified by free electrons and positive charges present in its orbital.

The Electrophile typically goes electrophilic addition reaction and electrophilic substitution reaction, while on the flip side, the Nucleophile goes through nucleophilic addition reaction and nucleophilic substitution reaction. An Electrophile is interchangeably known as lewis acids as it accepts electrons; in its comparison, a Nucleophile is interchangeably known as lewis bases because it donates electrons.

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The Electrophile is known as electron-deficient species; on the other hand, the Nucleophile is electron-rich specie. All Electrophiles are carbocations; on its contrary, all Nucleophiles are carbanions. The example of Electrophile is hydronium ion or hydrogen ions; on the flip side, the example of Nucleophile is chloride ions, or hydroxide ions, or ammonia.

Comparison Chart

ElectrophileNucleophile
The electron loving species are known as electrophiles, and they are electron-deficient species.The nucleus loving species or having an excess of species are known as nucleophiles, and they are electron-pair donors.
Considered As
Considered as a molecule or atom that can readily receive an electron pair mainly from the electron-rich atom, ion, or moleculeConsidered as an ion, a molecule or an atom which contains a high density of electrons and preferably donates pair of electrons
Covalent Bond Formation
After accepting a pair of the electron, it produces a covalent bondDonates a lone pair to produce a covalent bond
Electrical Charge
Exist as either positively charged, or neutrally chargedPresent as either negatively charged or neutrally charged
Chemical Reactions
Usually goes electrophilic addition reaction and electrophilic substitution reactionGoes through nucleophilic addition reaction and nucleophilic substitution reaction
Identified By
Identified by formal positive charge, a partial positive charge, and a neutral ion, atom, or molecule which does not obey the octet ruleIdentified by free electrons and positive charges present in its orbital
Other Names
Interchangeably known as lewis acids as it accepts electronsInterchangeably known as lewis bases because it donates electrons
Types
Positive electrophiles

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Neutral electrophiles

Negative nucleophiles

Neutral nucleophiles

Examples
The example is hydronium ion or hydrogen ionsThe example of Nucleophile is chloride ions, or hydroxide ions, or ammonia

What is Electrophile?

The Electrophile is known as a molecule or an atom, which is an electron-loving specie. The Electrophile readily accepts a pair of electrons from electron-rich species, which include atoms, molecules, or ions, and after accepting the electrons, it forms a covalent bond. Electrophile contains positively charged or negatively charged molecules or atoms, which consists of free orbitals for accepting the received electrons.

Lewis acids are another name for Electrophiles because of their capability to receive electrons. The Electrophile is formed when a molecule or an atom does not have electrons to satisfy the octet rule and consists of a positive charge which is required to be neutralized to become more stable.

For instance, H3O+ (hydronium ion) is known as an electrophile, and it consists of a positive charge; the hydrogen atom contains an open space for receiving electrons. So it accepts a pair of electrons from a nucleophile as –OH to produce the H2O molecule.

The Electrophile goes through electrophilic addition and substitution reaction in organic chemistry. Such as the adding of halogens into the alkenes done through an electrophilic addition reaction. In a substitution reaction, the substitution of Electrophile occurs by replacing the molecule’s functional group.

What is Nucleophile?

The Nucleophile is known as a molecule or an atom which readily donates the pair of electrons. Because of this capability of Nucleophile, it is also known as Lewis base. Molecules that consist of pi bonds and atoms or molecules consisting of free pair of electrons perform as nucleophiles.

Nucleophiles can also give electrons explicitly to the Electrophile. Nucleophiles are generally negatively charged, and all nucleophiles are carbanions because they donate electrons. The neutrally charged molecules having an electron-rich atom can also act as nucleophiles. The Nucleophile goes through specific reactions like nucleophilic substitution and nucleophilic addition reactions.

Regarding nucleophiles, a vital term, Nucleophilicity, is present. The term Nucleophilicity tells the strength of a specific nucleophile. Various factors such as polarizability, basicity, charge, etc. are present on which Nucleophilicity rest on mainly. For instance, when the nucleophilic negative charge is increased, ultimately, the Nucleophilicity is increased, this means that nucleophiles having a high strength of negative charge perform as an excellent nucleophile.

Nucleophiles usually are rich in electrons, so they quickly give electrons to electrophiles to produce the covalent bond during their reaction. Examples of Nucleophile are iodide, ammonia, and hydroxide ions.

Key Differences

  1. Electrophiles are known as electron-loving species, while on the other hand, Nucleophile is known as electron-donating specie.
  2. Still, Electrophile contains positively charged and neutrally charged electrons, atoms, and ions, whereas Nucleophile contains negatively charged and neutrally charged atoms, ions, and electrons.
  3. The Electrophile is referred as an atom or molecule that can freely obtain a pair of an electron from electron-rich species such as an atom, ion, or molecule; on the other hand, the Nucleophile is referred as a molecule, an ion or an atom which consist of the high density of electrons and freely donates pair of electrons.
  4. The electrophilic addition reactions and electrophilic substitution reactions are those reactions from which Electrophile undergoes; on the contrary, the nucleophilic addition reactions and nucleophilic substitution reactions occur in Nucleophile.
  5. Electrophile readily accepts electrons, so it is also known as Lewis acids. At the same time, in its comparison, the Nucleophile readily donates electrons to other species, so it is also known as Lewis bases.
  6. The formal positive charge, a partial positive charge, and a neutral ion, atom, or molecule (which does not obey the octet rule) are the ways to identify the Electrophile; on the flip side, free electrons and positive charges (present in nucleophilic orbital) are the specific ways to identifying the Nucleophile.
  7. All Electrophiles are generally carbocations. In its comparison, all Nucleophiles are known as carbanions.
  8. Hydronium ions or hydrogen ions are examples of Electrophile, while chloride ions, hydroxide ions, or ammonia are the example of Nucleophile.

Conclusion

The above discussion concludes that the Electrophile is electron-deficient specie, whereas the Nucleophile is referred to as electron-rich specie.

Harlon Moss

Harlon currently works as a quality moderator and content writer for Difference Wiki. He graduated from the University of California in 2010 with a degree in Computer Science. Follow him on Twitter @HarlonMoss

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