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  2. Antiaromaticity - Wikipedia

    en.wikipedia.org/wiki/Antiaromaticity

    The term 'antiaromaticity' was first proposed by Ronald Breslow in 1967 as "a situation in which a cyclic delocalisation of electrons is destabilising". [4] The IUPAC criteria for antiaromaticity are as follows: [5] The molecule must be cyclic. The molecule must be planar. The molecule must have a complete conjugated π-electron system within ...

  3. Hückel's rule - Wikipedia

    en.wikipedia.org/wiki/Hückel's_rule

    Benzene, the most widely recognized aromatic compound with six delocalized π-electrons (4n + 2, for n = 1).. In organic chemistry, Hückel's rule predicts that a planar ring molecule will have aromatic properties if it has 4n + 2 π-electrons, where n is a non-negative integer.

  4. Baird's rule - Wikipedia

    en.wikipedia.org/wiki/Baird's_rule

    In organic chemistry, Baird's rule estimates whether the lowest triplet state of planar, cyclic structures will have aromatic properties or not. The quantum mechanical basis for its formulation was first worked out by physical chemist N. Colin Baird at the University of Western Ontario in 1972.

  5. Möbius aromaticity - Wikipedia

    en.wikipedia.org/wiki/Möbius_aromaticity

    In contrast to the rarity of Möbius aromatic ground state molecular systems, there are many examples of pericyclic transition states that exhibit Möbius aromaticity. The classification of a pericyclic transition state as either Möbius or Hückel topology determines whether 4N or 4N + 2 electrons are required to make the transition state aromatic or antiaromatic, and therefore, allowed or ...

  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. Category:Antiaromatic compounds - Wikipedia

    en.wikipedia.org/wiki/Category:Antiaromatic...

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  8. Annulene - Wikipedia

    en.wikipedia.org/wiki/Annulene

    Annulenes may be aromatic (benzene, [6]annulene and [18]annulene), non-aromatic ([8] and [10]annulene), or anti-aromatic (cyclobutadiene, [4]annulene). Cyclobutadiene is the only annulene with considerable antiaromaticity, since planarity is unavoidable.

  9. Cyclobutadiene - Wikipedia

    en.wikipedia.org/wiki/Cyclobutadiene

    The compound is the prototypical antiaromatic hydrocarbon with 4 pi electrons (or π electrons). It is the smallest [n]-annulene ([4]-annulene).Its rectangular structure is the result of a pseudo [3] - (or second order) Jahn–Teller effect, which distorts the molecule and lowers its symmetry, converting the triplet to a singlet ground state. [4]