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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.
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 ...
Resonance structures of a semiquinone. Semiquinones (or ubisemiquinones, if their origin is ubiquinone) are free radicals resulting from the removal of one hydrogen atom with its electron during the process of dehydrogenation of a hydroquinone, such as hydroquinone itself or catechol, to a quinone or alternatively the addition of a single hydrogen atom with its electron to a quinone. [1]
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]
In another case, the stereoelectronic effect can result in an increased contribution of one resonance structure over another, which leads to further consequences in reactivity. For 1,4- benzoquinone monoxime, there are significant differences in the physical properties and reactivities between C2-C3 double bond and C5-C6 double bond.
Although the electronic structure according to valence bond theory can be written as H−N=C=O, the vibrational spectrum has a band at 2268.8 cm −1 in the gas phase, which some say indicates a carbon–nitrogen triple bond. [10] [11] If so, then the canonical form H−N + ≡C−O − is the major resonance structure.
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Bonding in the cyano radical can be described as a combination of two resonance structures: the structure with the unpaired electron on the carbon is the minor contributor, while the structure with the unpaired electron on the nitrogen (the isocyano radical) is the major contributor.