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aromatic compound
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AROMATIC COMPOUND

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By Francis A. Carey • Edit History

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aromatic compound
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Key People: Rudolf Fittig Wilhelm Körner ...(Show more) Related Topics:
nonbenzenoid aromatic compound aromatic ring Hückel rule aromatic acid benzenoid
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aromatic compound, any of a large class of unsaturated chemical compounds
characterized by one or more planar rings of atoms joined by covalent bonds of
two different kinds. The unique stability of these compounds is referred to as
aromaticity. Although the term aromatic originally concerned odour, today its
use in chemistry is restricted to compounds that have particular electronic,
structural, or chemical properties. Aromaticity results from particular bonding
arrangements that cause certain π (pi) electrons within a molecule to be
strongly held. Aromaticity is often reflected in smaller than expected heats of
combustion and hydrogenation and is associated with low reactivity.

Benzene (C6H6) is the best-known aromatic compound and the parent to which
numerous other aromatic compounds are related. The six carbons of benzene are
joined in a ring, having the planar geometry of a regular hexagon in which all
of the C—C bond distances are equal. The six π electrons circulate in a region
above and below the plane of the ring, each electron being shared by all six
carbons, which maximizes the force of attraction between the nuclei (positive)
and the electrons (negative). Equally important is the number of π electrons,
which, according to molecular orbital theory, must be equal to 4n + 2, in which
n = 1, 2, 3, etc. For benzene with six π electrons, n = 1.


chemical bonding in benzene
Benzene is the smallest of the organic aromatic hydrocarbons. It contains sigma
bonds (represented by lines) and regions of high-pi electron density, formed by
the overlapping of p orbitals (represented by the dark yellow shaded area) of
adjacent carbon atoms, which give benzene its characteristic planar structure.
Encyclopædia Britannica, Inc.
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chemical compound: Aromatic hydrocarbons (arenes)
A distinctive set of physical and chemical properties is imparted to molecules
that contain a functional group composed of three pairs of...

The largest group of aromatic compounds are those in which one or more of the
hydrogens of benzene are replaced by some other atom or group, as in toluene
(C6H5CH3) and benzoic acid (C6H5CO2H). Polycyclic aromatic compounds are
assemblies of benzene rings that share a common side—for example, naphthalene
(C10H8). Heterocyclic aromatic compounds contain at least one atom other than
carbon within the ring. Examples include pyridine (C5H5N), in which one nitrogen
(N) replaces one CH group, and purine (C5H4N4), in which two nitrogens replace
two CH groups. Heterocyclic aromatic compounds, such as furan (C4H4O), thiophene
(C4H4S), and pyrrole (C4H4NH), contain five-membered rings in which oxygen (O),
sulfur (S), and NH, respectively, replace an HC=CH unit.

Francis A. Carey



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While every effort has been made to follow citation style rules, there may be
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sources if you have any questions.
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Carey, Francis A.. "aromatic compound". Encyclopedia Britannica, 24 Jun. 2008,
https://www.britannica.com/science/aromatic-compound. Accessed 22 April 2022.
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 * Fact Monster - Aromatic Compound


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