What are Nucleophiles?

 History: The terms nucleophile and electrophile were introduced by

Christopher Kelk Ingold in 1933. The word nucleophile is derived from
nucleus and the Greek word φιλος, philos, meaning friend. The word
‘nucleophile’ can be split into two parts, namely nucleus and philos. Philos
is the Greek word for ‘love’. Therefore, nucleophiles can be thought of as
Nucleus Loving species. These nucleophiles may have either a negative or a
neutral charge.

Definition of Nucleophile: Nucleophile is a word used to refer to substances

that tend to donate electron pairs to electrophiles in order to form chemical bonds
with them. Any ion or molecule having an electron pair which is free or a pi bond
containing two electrons has the ability to behave like nucleophiles.

Nucleophiles are basically electron-rich species which have the ability to donate
electron pairs, because of this electron pair donating tendency, all nucleophiles are
Lewis Bases.

Examples: Examples of nucleophiles are the halogen anions (I-, Cl-, Br-), the
hydrxide ion (OH-), the cyanide ion (CN-), ammonia (NH3), and water.

Some terminologies regarding nucleophiles:

 The nucleophilic nature of a species describes the affinity of the species to
the positively charged nucleus.
  Nucleophilicity is a word used to compare the nucleophilic character of
different nucleophiles. It can also be called the nucleophile strength of a
species.
 Nucleophilic substitution is a type of reaction that occurs when an electron-
rich nucleophile selectively attacks a positively charged (or a partially
positively charged) atom in a molecule and replaces a leaving group by
bonding with the positively charged species.

Types of Nucleophiles:
Commonly, the following species form good nucleophiles, here’s some types of
nucleophiles are discussed:

 Halogens, the diatomic form of a halogen does not exhibit nucleophilic

qualities. However, the anionic forms of these halogens are great
nucleophiles. I– is the strongest nucleophile in a polar, protic solvent.
 Carbon, carbon acts as a nucleophile in many organometallic reagents and
also in enols. Some examples of compounds wherein carbon acts as a
nucleophile include Grignard Reagents, Organo-lithium Reagents, and n-
butyllithium.
 Oxygen, the hydroxide ion is a great example of a nucleophile where in the
electron pair is donated by the oxygen atom. It is important to note that no
nucleophilic attacks occur during the intermolecular hydrogen bonding that
takes place in many compounds containing oxygen and hydrogen.
 Sulphur, due to the large size, the relative ease in its polarization, and the
easily accessible lone electron pairs, sulphur has many nucleophilic
qualities. Hydrogen sulphide (H2S) is a great example of a nucleophile
containing sulphur.
 Nitrogen, nitrogen is known to form many nucleophiles such as amines,
azides, ammonia, and nitrides. Even amides are known to exhibit
nucleophilic qualities.