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Aromatic Compounds

An aromatic compound is a organic molecule containing a benzene


ring.
Any of a large class of organic compounds whose molecular structure includes one or
more planar rings of atoms, usually but not always six carbon atoms. The ring's carboncarbon bonds (bonding) are neither single nor double but a type characteristic of these
compounds, in which electrons are shared equally with all the atoms around the ring in an
electron cloud. The term was first applied 1860 to a class of hydrocarbons isolated from
coal tar and distinguished by odours much stronger than those of other classes of
hydrocarbons. In modern chemistry, aromaticity denotes the chemical behaviour,
especially the low reactivity, of this class of molecules related to their bonding. The
parent compound of this class is benzene (C6H6).Hydrogenation.
The general rule is that aromatic molecules have 4n + 2 delocalized electrons (where n is
an integral number). Thus the number of delocalized electrons in benzene (6),
naphthalene (10), and anthracene (14) agree with their aromatic character. On the other
hand, the eight-membered cyclic compound with four alternating double bonds
(cyclooctatetraene) is not aromatic and shows reactivity similar to alkanes. For this
reason, the bonds in the aromatic ring are less reactive than ordinary double bonds;
aromatic compounds tend to undergo ionic substitution (e.g., replacement of a hydrogen
bonded to the ring with some other group) rather than addition (which would involve
breaking one of the resonant bonds in the ring).
The constant shifting of charge is called the electron cloud. This makes for a very stable
molecule. Few purely aromatic compounds are GRAS; in fact, benzene (one ring) and
naphthalene (two connected rings) are quite harmful and toxic, with mutagenic and
carcinogenic properties
Originally applied to a small class of pleasant-smelling chemicals derived from
vegetables, it now encompasses a wide diversity of compounds with no connection to the
sense of smell. Common aromatic compounds other than benzene include toluene,
naphthalene, and anthracene (all of which are present in coal tar). Each of these
compounds contains at least one ring that consists of six carbon atoms, each joined to at
least two other carbon atoms, and each joined to adjacent carbon atoms by one single and
one double bond. The resulting hexagonal structure is characteristic of many aromatic
compounds.

Drugs of Aromatic Compounds

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Aromatic Chemistry

Aromatic Compounds (Overview)

Aromatic Compounds (Overview)


Benzene: An Aromatic Compound
The compound which is today known as benzene was isolated for the first time in 1824 by
Michael Faraday. He found it in the liquid residue that condensed from the gas phase when
whale oil was burnt by the street lamps in London. Initially, the name "pheno", which derives
from the Greek word "phainein" (= shine), was proposed.
Ten years later, in 1834, Eilhardt Mitscherlich determined the correct empirical formula of
benzene: C6H6. Due to the chemical relationship it has with benzoic acid, he called it benzin. It
was only later on that the name "benzin" was replaced by "benzene".
The relatively low number of hydrogens in proportion to the number of carbons is characteristic
of aromatic compounds. Aromatic compounds are usually found tree and plant oils. While
benzaldehyde is found in cherries and peaches, toluene may be isolated from the trunk of the
South American Myroxylon balsamum tree, for instance. Benzene is obtained by distillation of
coal. Due to their aromatic and often pleasant smell, the name "aromatic compounds" was given
to the members of this family. Many natural products, such as the hormone oestrone and the
opiate morphine, contain aromatic parts and synthetic products, such as the sedative drug valium,
too.

Examples of naturally occuring and synthetic aromatic compounds

Fig.1
Benzene
Fig.2
Benzaldehyde
Fig.3
Toluene
Tab.1
Naturally occuring and synthetic aromatic compounds
Oestrone
Morphine

Fig.4

Mouse
Fig.7

Fig.5

Mouse
Fig.8

Diazepam (valium)

Fig.6

Mouse
Fig.9

Further "daily" aromatic compounds are saccharine (a synthetic sweetener), benzopyrene (a


carcinogenic compound, which is formed when meat is broiled), the anthraquinone dye 1,4diaminoanthraquinone (a purple hair dye), and (2,4,5-trichlorophenoxy)acetic acid. This acetic
acid derivative is a defolient that was used during the Vietnam War. In its synthesis the "Seveso
poison" 2,3,7,8-tetrachlorodibenzo[b,e]-p-dioxin appears as a side product. This dioxin is also
formed as a by-product when aromatic and chlorine-containing compounds are improperly burnt
in an incineration plant.

Nowadays, the chemical meaning of the term "aromatic" is no longer correlated with the
compound's smell. The term "aromatic" now applies to a family of compounds whose members
are structurally related in that they contain an aromatic system. The chemical behavior of
aromatic compounds is considerably different from that of aliphatic compounds.
The effects of exposure to benzene over a longer period of time are, among others, bone-marrow
atrophy and leukemia. This is commonly the case even if the concentration of benzene is
relatively small. Great precautions must therefore be taken when working with benzene.