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  2. Clar's rule - Wikipedia

    en.wikipedia.org/wiki/Clar's_rule

    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 ...

  3. Resonance (chemistry) - Wikipedia

    en.wikipedia.org/wiki/Resonance_(chemistry)

    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.

  4. Benzene - Wikipedia

    en.wikipedia.org/wiki/Benzene

    Benzene and cyclohexane have a similar structure, only the ring of delocalized electrons and the loss of one hydrogen per carbon distinguishes it from cyclohexane. The molecule is planar. [ 58 ] The molecular orbital description involves the formation of three delocalized π orbitals spanning all six carbon atoms, while the valence bond ...

  5. Cyclic compound - Wikipedia

    en.wikipedia.org/wiki/Cyclic_compound

    This configuration allows for the electrons in the molecule's pi system to be delocalized around the ring, increasing the molecule's stability. The molecule cannot be represented by one structure, but rather a resonance hybrid of different structures, such as with the two resonance structures of benzene.

  6. Aromaticity - Wikipedia

    en.wikipedia.org/wiki/Aromaticity

    Two different resonance forms of benzene (top) combine to produce an average structure (bottom). In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected by the stabilization of conjugation alone.

  7. Electrophilic aromatic directing groups - Wikipedia

    en.wikipedia.org/wiki/Electrophilic_aromatic...

    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.

  8. Heterocyclic compound - Wikipedia

    en.wikipedia.org/wiki/Heterocyclic_compound

    A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). [1] Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of organic heterocycles .

  9. Arenium ion - Wikipedia

    en.wikipedia.org/wiki/Arenium_ion

    Two hydrogen atoms bonded to one carbon lie in a plane perpendicular to the benzene ring. [4] The arenium ion is no longer an aromatic species; however it is relatively stable due to delocalization: the positive charge is delocalized over 3 carbon atoms by the pi system , as depicted on the following resonance structures :