Nucleophile

A chemical species that donates an electron pair to form a bond with an electron-deficient atom or group. Nucleophiles may be negatively charged or neutral molecules with available electron pairs.

Lewis base: A species that donates an electron pair to form a coordinate covalent bond. Nucleophiles are Lewis bases whose electron-pair donation forms a bond to an electrophilic site.
Lone pair: A pair of valence electrons not shared in a covalent bond. Many neutral nucleophiles donate a lone pair to form a new bond.
Basicity: A measure of a species' tendency to accept a proton. Basicity concerns proton acceptance; nucleophilicity concerns bond formation at an electrophilic atom.
Hydroxide: The negatively charged ion OH⁻, a strong base and common nucleophile. Hydroxide attacks electrophilic carbon centers and can also promote elimination.
Solvent effects: Changes in reaction behavior caused by the interactions between solute molecules and solvent. Solvation can stabilize a nucleophile and alter how readily it attacks.
Electrophile: An electron-deficient atom, ion, or molecule that accepts an electron pair to form a bond. It accepts the pair that a nucleophile supplies.
Formal charge: An assigned charge on an atom calculated by dividing bonding electrons equally between bonded atoms. Negative formal charge often signals electron-rich species, though it does not alone determine nucleophilicity.
Nucleophilicity: The kinetic tendency of a species to attack an electrophile and form a bond. This related property describes reaction speed rather than electron-pair donation as a species role.
Cyanide: The ion CN⁻, a nucleophile that forms carbon–carbon bonds in organic reactions. Cyanide adds a carbon atom when it attacks suitable electrophiles.
SN1 reaction: A unimolecular nucleophilic substitution that proceeds through a carbocation intermediate. Unlike SN2, its rate does not depend directly on nucleophile concentration in the rate-determining step.

Linked from 35 pages