Everything about Aromatic Ring totally explained
An
aromatic hydrocarbon (abbreviated as AH) or
arene is a
hydrocarbon, of which the
molecular structure incorporates one or more planar sets of six
carbon atoms that are connected by
delocalised electrons numbering the same as if they consisted of alternating single and double
covalent bonds. The term 'aromatic' was assigned before the physical mechanism determining
aromaticity was discovered, and was derived from the fact that many of the compounds have a sweet scent. This sweet scent actually came from impurities in the compounds (which are not actually aromatic in the sense initially described). The configuration of six carbon atoms in aromatic compounds is known as a
benzene ring, after the simplest possible such hydrocarbon,
benzene. Aromatic hydrocarbons can be
monocyclic or
polycyclic.
Some non-benzene-based compounds called
heteroarenes, which follow
Hückel's rule, are also aromatic compounds. In these compounds, at least one carbon atom is replaced by one of the
heteroatoms
oxygen,
nitrogen, or
sulfur. Examples of non-benzene compounds with aromatic properties are
furan, a heterocyclic compound with a five-membered ring that includes an oxygen atom, and
pyridine, a heterocyclic compound with a six-membered ring containing one nitrogen atom.
Benzene ring model
Benzene, C
6H
6, is the simplest AH and was recognized as the first aromatic hydrocarbon, with the nature of its bonding first being recognized by
Friedrich August Kekulé von Stradonitz in the 19th century.
Each carbon atom in the hexagonal cycle has four electrons to share. One goes to the hydrogen atom, and one each to the two neighboring carbons. This leaves one to share with one of its two neighboring carbon atoms, which is why the benzene molecule is drawn with alternating single and double bonds around the hexagon.
Many chemists draw a circle around the inside of the ring to show six electrons floating around in delocalized molecular orbitals the size of the ring itself. This also accurately represents the equivalent nature of the six bonds all of
bond order ~1.5. This equivalency is well explained by
resonance forms. The electrons float above and below the ring, and the electromagnetic fields they generate keep the ring flat.
General properties:
- Display aromaticity.
- The Carbon-Hydrogen ratio is very large.
- They burn with a sooty yellow flame because of the high carbon-hydrogen ratio.
- They undergo electrophilic substitution reactions and nucleophilic aromatic substitutions.
Arene synthesis
Many laboratory methods exist for the
organic synthesis of arenes from non-arene precursors:
Alkyne trimerization, [2+2+2] cyclization of three alkynes
Dötz reaction
Diels-Alder reactions of alkynes with pyrone or cyclopentadienone with expulsion of carbon dioxide or carbon monoxide.
Aromatization of cyclohexanes and other aliphatic rings: reagents are, catalysts used in hydrogenation such as platinum, palladium and nickel (reverse hydrogenation), quinones and the elements sulfur and selenium .
Bergman cyclization, enyne plus hydrogen donor
Arene reactions
The main arene reactions are
Electrophilic aromatic substitution
Nucleophilic aromatic substitution
Many coupling reactions to biraryls
Hydrogenation to saturated rings
Lesser-known reactions:
Unusual thermal Diels-Alder reactivity of arenes can be found in the Wagner-Jauregg reaction
Other photochemical cycloaddition reactions with alkenes through excimers.
Benzene and derivatives of benzene
Benzene derivatives have from one to six substituents attached to the central benzene core. Examples of benzene compounds with just one substituent are phenol, which carries a hydroxyl group and toluene with a methyl group. When there's more than one substituent present on the ring, their spatial relationship becomes important for which the arene substitution patterns ortho, meta, and para are devised. For example, three isomers exist for cresol because the methyl group and the hydroxyl group can be placed next to each other (ortho), one position removed from each other (meta), or two positions removed from each other (para). Xylenol has two methyl groups in addition to the hydroxyl group, and, for this structure, 6 isomers exist.
Examples of benzene derivatives with alkyl substituents (alkylbenzenes):
Ethylbenzene C6H5-CH2-CH3
Toluene C6H5-CH3
Xylene, m-Xylene, p-Xylene C6H4(-CH3)2
Mesitylene, Pseudocumene, Hemimellitene C6H3(-CH3)3
Prehnitene, Isodurene, Durene C6H2(-CH3)4
Pentamethylbenzene C6H(-CH3)5
Mellitene C6(-CH3)6
Examples of other aromatic compounds:
Aniline C6H5-NH2
Acetylsalicylic acid C6H4(-O-C(=O)-CH3)(-COOH)
Benzoic acid C6H5-COOH
Biphenyl (C6H5)2
Chlorobenzene C6H5-Cl
Nitrobenzene C6H5-NO2
Paracetamol C6H4(-NH-C(=O)-CH3)(-OH)
Phenacetin C6H4(-NH-C(=O)-CH3)(-O-CH2-CH3)
Phenol C6H5-OH
Picric acid C6H2(-OH)(-NO2)3
Salicylic acid C6H4(-OH)(-COOH)
Trinitrotoluene C6H2(-CH3)(-NO2)3
The arene ring has an ability to stabilize charges. This is seen in, for example, phenol (C6H5-OH), which is acidic at the hydroxyl (OH), since a charge on this oxygen (alkoxide -O–) is partially delocalized into the benzene ring.
Polyaromatic hydrocarbons
Some important arenes are the polyaromatic hydrocarbons (PAH); they're also called polycyclic aromatic hydrocarbons and polynuclear aromatic hydrocarbons. They are composed of more than one aromatic ring. The simplest PAHs are benzocyclopropene (C7H6), benzocyclopropane (C7H8), benzocyclobutadiene (C8H6), and benzocyclobutene (C8H8).
Common examples are naphthalene with two fused rings, anthracene with three, tetracene with four, and pentacene with five linearly fused rings. Phenanthrene and triphenylene are examples of non-linear connections. More exotic examples are helicenes and corannulene.
These compounds are one of the most widespread organic pollutants, remaining on beaches and marine environmentals for a long time after an oil spill. Recent investigations have concluced that their toxicity is up to 100 times worse than first assumed.
Further Information
Get more info on 'Aromatic Ring'.
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