Summary
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other element or compound to serve as a functional group. Phenyl group has six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, phenyl group is chemically aromatic and has equal bond lengths between carbon atoms in the ring. Usually, a "phenyl group" is synonymous with and is represented by the symbol Ph or, archaically, Φ. Benzene is sometimes denoted as PhH. Phenyl groups are generally attached to other atoms or groups. For example, triphenylmethane () has three phenyl groups attached to the same carbon center. Many or even most phenyl compounds are not described with the term "phenyl". For example, the chloro derivative is normally called chlorobenzene, although it could be called phenyl chloride. In special (and rare) cases, isolated phenyl groups are detected: the phenyl anion (), the phenyl cation (), and the phenyl radical (C6H5•). Although Ph and phenyl uniquely denote , substituted derivatives also are described using the phenyl terminology. For example, is nitrophenyl, and is pentafluorophenyl. Monosubstituted phenyl groups (that is, disubstituted benzenes) are associated with electrophilic aromatic substitution reactions and the products follow the arene substitution pattern. So, a given substituted phenyl compound has three isomers, ortho (1,2-disubstitution), meta (1,3-disubstitution) and para (1,4-disubstitution). A disubstituted phenyl compound (trisubstituted benzene) may be, for example, 1,3,5-trisubstituted or 1,2,3-trisubstituted. Higher degrees of substitution, of which the pentafluorophenyl group is an example, exist and are named according to IUPAC nomenclature.
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