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Conjugated system
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===Aromatic compounds=== Compounds that have a monocyclic, planar conjugated system containing [[4n+2 rule|(4''n'' + 2) π-electrons]] for whole numbers ''n'' are [[aromaticity|aromatic]] and exhibit an unusual stability. The classic example [[benzene]] has a system of six π electrons, which, together with the planar ring of C–C σ bonds containing 12 electrons and radial C–H σ bonds containing six electrons, forms the thermodynamically and kinetically stable ''[[benzene ring]]'', the common core of the benzenoid aromatic compounds. For benzene itself, there are two equivalent conjugated contributing Lewis structures (the so-called Kekulé structures) that predominate.<ref>{{Cite journal|last1=Rashid|first1=Zahid|last2=van Lenthe|first2=Joop H.|date=March 2011|title=Generation of Kekulé valence structures and the corresponding valence bond wave function|journal=Journal of Computational Chemistry|volume=32|issue=4|pages=696–708|doi=10.1002/jcc.21655|issn=1096-987X|pmid=20941739| s2cid=16526798 }}</ref><ref>While the two Kekulé resonance forms contribute to most (>90%) of the π bond energy, there are also a number of other minor contributors to the wavefunction in the valence bond treatment, including the three Dewar resonance forms, and even smaller contributions from various ionic and singlet diradical forms. See article by Rashid and van Lenthe for a recent computational treatment.</ref> The true electronic structure is therefore a quantum-mechanical combination (resonance hybrid) of these contributors, which results in the experimentally observed C–C bonds which are intermediate between single and double bonds and of equal strength and length. In the molecular orbital picture, the six p atomic orbitals of benzene combine to give six molecular orbitals. Three of these orbitals, which lie at lower energies than the isolated p orbital and are therefore net bonding in character (one molecular orbital is strongly bonding, while the other two are equal in energy but bonding to a lesser extent) are occupied by six electrons, while three destabilized orbitals of overall antibonding character remain unoccupied. The result is strong thermodynamic and kinetic aromatic stabilization. Both models describe rings of π electron density above and below the framework of C–C σ bonds.
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