|
Whereas electrophiles have areas of electron deficiency, nucleophiles
have areas that are electron rich. A nucleophilic "nucleus-loving"
species will tend to attack electron-deficient areas.e.g.:

|
Chloromethane (left) has an electron deficient carbon
atom due to the presence of the inductively withdrawing chlorine
atom. This is therefore most readily attacked by negatively charged
species (OH-, CN- etc.), or by species with
an electron rich area such as a lone pair of electrons (H3N:
etc.). |
It must be stressed that there only needs to be a
small imbalance in charge to favour a reaction along one path.
However, a large charge imbalance is certainly not an impediment
to the reaction. In some cases, the charge imbalance itself is caused
by the approach of the reagents themselves, e.g. bromine and ethene:
The concept of electrophiles and nucleophiles may
remind you of acids
and bases, which is not surprising, as there are many similarities.
The Brønsted
definition of an acid is a proton donator, and that of a base is
a proton acceptor, and the Lewis definition generalised this to
include acids as electron pair acceptors, and bases as electron
pair donors. This definition therefore includes some species
not previously thought of as acids and bases e.g. boron trifluoride:
The Lewis definition of acids and bases is quite similar
to electrophiles and nucleophiles, the former being essentially
electron acceptors, and the latter being electron donors.
Electrophiles and nucleophiles also bear a relationship to oxidizing
and reducing agents. Oxidizing agents can be viewed as electron
donors, and reducing agents can be viewed as electron acceptors.
| Electrophiles |
Nucleophiles |
| H+ |
H- |
| +NO2 |
BH4- |
| +NO |
HO- |
| PhN2+ |
RO- |
| R3C+ |
RS- |
| +SO3 |
-CN |
| BF3 |
RCC- |
The table above may prove useful as a reference guide
to various common electrophiles and nucleophiles.
|
|