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Contributing structures of the carbonate ion. In chemistry, resonance, also called mesomerism, is a way of describing bonding in certain molecules or polyatomic ions by the combination of several contributing structures (or forms, [1] also variously known as resonance structures or canonical structures) into a resonance hybrid (or hybrid structure) in valence bond theory.
In chemistry, the mesomeric effect (or resonance effect) is a property of substituents or functional groups in a chemical compound.It is defined as the polarity produced in the molecule by the interaction of two pi bonds or between a pi bond and lone pair of electrons present on an adjacent atom. [1]
Expressing resonance when drawing Lewis structures may be done either by drawing each of the possible resonance forms and placing double-headed arrows between them or by using dashed lines to represent the partial bonds (although the latter is a good representation of the resonance hybrid which is not, formally speaking, a Lewis structure ...
However, resonance can also be detrimental, leading to excessive vibrations or even structural failure in some cases. [3] All systems, including molecular systems and particles, tend to vibrate at a natural frequency depending upon their structure; this frequency is known as a resonant frequency or resonance frequency.
A valence bond structure resembles a Lewis structure, but when a molecule cannot be fully represented by a single Lewis structure, multiple valence bond structures are used. Each of these VB structures represents a specific Lewis structure. This combination of valence bond structures is the main point of resonance theory.
Clar's rule states that for a benzenoid polycyclic aromatic hydrocarbon (i.e. one with only hexagonal rings), the resonance structure with the largest number of disjoint aromatic π-sextets is the most important to characterize its chemical and physical properties. Such a resonance structure is called a Clar structure. In other words, a ...
On the other hand, the nitrobenzene resonance structures have positive charges around the ring system: The nitro group can withdraw electron density through resonance. Attack occurs at the meta position, since the (partial) formal positive charges at the ortho and para positions indicate electron deficiency at these positions.
In the simple aromatic ring of benzene, the delocalization of six π electrons over the C 6 ring is often graphically indicated by a circle. The fact that the six C-C bonds are equidistant is one indication that the electrons are delocalized; if the structure were to have isolated double bonds alternating with discrete single bonds, the bond would likewise have alternating longer and shorter ...