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Nucleophile vs Electrophile

Electrophile and Nucleophile are studies in general organic chemistry (GOC). Electrophile or Nucleophile is basically any chemical species that can accept or donate electrons to form a new chemical bond. We are going to dive deep into the comparison- Nucleophile vs Electrophile.

History

A British chemist named Christopher Kelk Ingold from London introduced the term Electrophile and Nucleophile in 1933. He served for 24 years as head of the chemistry department at University College London.

Christopher Kelk Ingold introduced the term Electrophile and Nucleophile in 1933.
Christopher Kelk Ingold (Source)

Nucleophile vs Electrophile Explained

Electrophile: It is a chemical species that has positively charged (cation) or neutrally charged. Electrophile forms bonds with nucleophiles by accepting electron pairs. Atoms that carry a partial positive charge or have atoms that do not have an octet of electrons can act as electrophile. Electrophile are also called species that love electrons.

  • The term electrophile can be splitted into two parts.
    Electro = Electrons and Phile = Loving
  • They move from high density areas to low density areas.
  • Electrophile is also known as lewis acid.
  • They attract electrons.

Nucleophile: It is a chemical species that has negatively charge (anion). Nucleophiles form bonds with electrophile by donating electrons pairs. The molecules and ions which have a free pair of electrons or at least a single pi bond can act as nucleophile. Nucleophiles are also called species that love nucleus .

  • The term nucleophile can be splitted into two parts.
    Nucleo = Nucleus and Phile = Loving
  • They move from low density area to high density area.
  • Nucleophile is know as lewis acid.
  • They donate electrons.

Let’s look at the table below showing comparison of nucleophile vs electrophile.

ELECTROPHILENUCLEOPHILE
1. Known as lewis acid  1. Known as lewis base
2. They are positively charged 2. They are negatively charged
3. They attract electron3. They Donate Electron
4. All carbocation 4. All carbanions
Ex: Hydronium ionEx: Chloride ion

Applications

Electrophile and Nucleophile are used in General Organic Chemistry (GOC). Electrophile and nucleophile mainly interact with each other by addition or substitution reaction thus are involved in major reactions.

Examples for Nucleophile vs Electrophile

Lets see some example related to nucleophile vs electrophile.

Examples of electrophile are:-

  1. Positively Charged Electrophile:
    • H+, SO3H+, NO+, NO2+, C6H5N2+
  2. Neutral Electrophile:
    • All the Lewis acid are neutral electrophile
      BF3, AlCl3, SO3, ZnCl2, BeCl2, FeCl3, CO2

Examples of nucleophile are:-

  1. Negatively charged nucleophile:
    • H, OH, CN
  2. All the Lewis base which contain lone pair are nucleophile:
    • R*-Mg-X , CH3-CH*

FAQs

What is electrophile ?

It is a chemical species that has positively charged (cation). Electrophile forms bonds with nucleophiles by accepting electron pairs. Atoms that carry a partial positive charge or have atoms that do not have an octet of electrons can act as electrophile.

What is nucleophile ?

It is a chemical species that has negatively charge (anion). Nucleophiles form bonds with electrophile by donating electrons pairs. The molecules and ions which have a free pair of electrons or at least a single pi bond can act as nucleophile.

What is the example of positively charged electrophile?

H+, SO3H, NO+, NO2+

What is the example of a negatively charged nucleophile?

H, OH, CN

Read About Reaction Mechanisms

SN1 ReactionSN2 Reaction
E1 ReactionE2 Reaction
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