Charge Distribution

If the electron pairs in covalent bonds were donated and shared absolutely evenly there would be no fixed local charges within a molecule. Although this is true for diatomic elements such as H₂, N₂ and O₂, most covalent compounds show some degree of local charge separation, resulting in bond and / or molecular dipoles. A dipole exists when the centers of positive and negative charge distribution do not coincide.

Formal Charges

A large local charge separation usually results when a shared electron pair is donated unilaterally. The three Kekulé formulas shown here illustrate this condition.

In the formula for ozone the central oxygen atom has three bonds and a full positive charge while the right hand oxygen has a single bond and is negatively charged. The overall charge of the ozone molecule is therefore zero. Similarly, nitromethane has a positive-charged nitrogen and a negative-charged oxygen, the total molecular charge again being zero. Finally, azide anion has two negative-charged nitrogens and one positive-charged nitrogen, the total charge being minus one.
In general, for covalently bonded atoms having valence shell electron octets, if the number of covalent bonds to an atom is greater than its normal valence it will carry a positive charge. If the number of covalent bonds to an atom is less than its normal valence it will carry a negative charge. The formal charge on an atom may also be calculated by the following formula:

مواضيع ذات صلة

Organic compounds are more soluble in water as ions

Heterocyclic aromatic compounds

Hückel’s rule tells us if compounds are aromatic

Molecular orbitals and aromaticity

The π molecular orbitals of other conjugated cyclic hydrocarbons

Benzene has six π molecular orbitals

Varying the number of electrons

Heats of hydrogenation of benzene and cyclooctatetraene

? What makes benzene special

Aromaticity

Conjugation and reactivity: looking forward to Chapter 10

The amide group