phenomenon providing chemical stability in resonating hybrids of cyclic organic compounds

In organic chemistry, aromaticity is formally used to describe an unusually stable nature of some flat rings of atoms. These structures contain a number of double bonds that interact with each other according to certain rules. As a result of their being so stable, such rings tends to form easily, and once formed, tend to be difficult to break in chemical reactions.


  • Simple aromatic hydrocarbons come from two main sources: coal and petroleum. Coal is an enormously complex mixture made up primarily of large arrays of benzene-like rings joined together. Thermal breakdown of coal occurs when it is heated to 1000 °C in the absence of air, and a mixture of volatile products called coal tar boils off. Fractional distillation of coal tar yields benzene, toluene, xylene (dimethylbenzene), naphthalene, and a host of other aromatic compounds.
    Unlike coal, petroleum contains few aromatic compounds and consists largely of alkanes. (...) During petroleum refining, however, aromatic molecules are formed when alkanes are passed over a catalyst at about 500 °C under high pressure.
    • John McMurry, Organic Chemistry 8th ed. (2012), Ch. 15. Benzene and Aromaticity

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