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The structure of the phenyl group attached to an "R" group.

In organic chemistry, the phenyl group or phenyl ring is a cyclic group of atoms with the formula C₆H₅. Phenyl groups are closely related to benzene. Phenyl groups have 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.^[1] Although often depicted with alternating double and single bonds, phenyl groups are chemically aromatic and show nearly equal bond lengths between carbon atoms in the ring.^[1]^[2]

Nomenclature

Usually, a "phenyl group" is synonymous to C₆H₅– 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 (Ph₃CH) 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 C₆H₅Cl is normally called chlorobenzene, although it could be called phenyl chloride. In special (and rare) cases, isolated phenyl groups are detected: the phenyl anion (C₆H₅⁻), the phenyl cation (C₆H₅⁺), and the phenyl radical (C₆H₅^·).

Although Ph and phenyl uniquely denote C₆H₅, substituted derivatives also are described using the phenyl terminology. For example, O₂NC₆H₄ is nitrophenyl (of which three isomers are possible) and F₅C₆ is pentafluorophenyl.

Etymology

Phenyl is derived from the French word phényle, which in turn derived from Greek phaino – "shining", as the first phenyl compounds were byproducts of lighting gases.^[3]

Structure, bonding, characterization

Phenyl compounds are derived from benzene (C₆H₆), at least conceptually and often in terms of their production. In terms of its electronic properties, the phenyl group is related to a vinyl group. The phenyl group is hydrophobic. Phenyl groups tend to resist oxidation and reduction. Phenyl groups (like all aromatic compounds) have enhanced stability in comparison to equivalent bonding in aliphatic (non-aromatic) groups. This increased stability is due to the unique properties of aromatic molecular orbitals.^[2]

The bond lengths between carbon atoms in a phenyl group are approximately 1.4 Å.^[4]

In ¹H-NMR spectroscopy, protons of a phenyl group typically have chemical shifts around 7.27 ppm. These chemical shifts are influenced by aromatic ring current and may change depending on substituents.

Preparation, occurrence, and applications

Phenyl groups are usually introduced using reagents that behave as sources of the phenyl anion or the phenyl cation. Representative reagents include phenyllithium (C₆H₅Li) and phenylmagnesium bromide (C₆H₅MgBr). Electrophiles attack benzene to give phenyl derivatives:

C₆H₆ + E⁺ → C₆H₅E + H⁺

where E⁺ (the "electrophile") = Cl⁺, NO₂⁺, SO₃. These reactions are called electrophilic aromatic substitutions.

Representative compounds containing phenyl groups
Atorvastatin (Lipitor), a blockbuster drug featuring two phenyl and one p-fluorophenyl groups. It is used to lower cholesterol in people with hypercholesterolaemia.
Fexofenadine (Allegra, Telfast), another blockbuster drug, which features a diphenylmethyl group as well as a p-phenylene (C₆H₄) group. It is an antihistamine used to treat allergies.
Phenylalanine, a common amino acid.
Biphenyl, consisting of two phenyl groups. The two rings tend not to be coplanar.
Chlorobenzene (or phenyl chloride), a solvent.

Phenyl groups are found in many organic compounds, both natural and synthetic (see figure). Most common among natural products is the amino acid phenylalanine, which contains a phenyl group. A major product of the petrochemical industry is "BTX" consisting of benzene, toluene, and xylene - all of which are building blocks for phenyl compounds. The polymer polystyrene is derived from a phenyl-containing monomer and owes its properties to the rigidity and hydrophobicity of the phenyl groups. Many drugs as well as many pollutants contain phenyl rings. biphe One of the simplest phenyl-containing compounds is phenol, C₆H₅OH. It is often said the resonance stability of phenol makes it a stronger acid than that of aliphatic alcohols such as ethanol (pK_a = 10 vs. 16–18). However, a significant contribution is the greater electronegativity of the sp² alpha carbon in phenol compared to the sp³ alpha carbon in aliphatic alcohols.^[5]

References

^ ^a ^b March, J. “Advanced Organic Chemistry” 4th Ed. J. Wiley and Sons, 1992: New York. ISBN 0-471-60180-2.
^ ^a ^b "Virtual Textbook of Organic Chemistry: Aromaticity". Michigan State University. http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/react3.htm
^ Oxford Dictionaries
^ Hendrik F. Hameka. "Computation of the structures of the phenyl and benzyl radicals with the UHF method". J. Org. Chem., 1987, 52 (22), pp. 5025–5026. http://pubs.acs.org/doi/abs/10.1021/jo00231a035
^ "Inductive and Resonance Effects on the Acidities of Phenol, Enols, and Carbonyl α-Hydrogens." Pedro J. Silva J. Org. Chem. 2009 (Solvation effects on the relative acidities of acetaldehyde enol and phenol described in the Supporting Information)

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English Journal

Immobilization of lipase on amino-cyclodextrin functionalized carbon nanotubes for enzymatic catalysis at the ionic liquid-organic solvent interface.

Li L, Feng W, Pan K.SourceDepartment of Biochemical Engineering, Beijing University of Chemical Technology, Beijing, China.
Colloids and surfaces. B, Biointerfaces.Colloids Surf B Biointerfaces.2013 Feb 1;102:124-9. doi: 10.1016/j.colsurfb.2012.07.050. Epub 2012 Aug 14.
Amino-cyclodextrin was covalently attached to multiwalled carbon nanotubes (MWNTs). The functionalized MWNTs have a good dispersibility in water. The lipase was adsorbed onto the functionalized MWNTs. The immobilized lipase was utilized for the resolution of the model compound (R, S)-1-phenyl ethano
PMID 23010110

Amygdalin induces apoptosis in human cervical cancer cell line HeLa cells.

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Japanese Journal

Versatile bridging ability of secondary thioamide group for constructing metal cluster based on pincer complex

Okamoto Ken,Kuwabara Junpei,Kanbara Takaki,桑原純平,神原貴樹
Journal of organometallic chemistry 696(6), 1305-1309, 2011-03
… The crystallization of the SCS pincer platinum complex with secondary thioamide groups, [4-methyl-2,6-bis(anilinothiocarbonyl)-κ2S,S’-phenyl-κC1]chloroplatinum(II), spontaneously forms a trinuclear cluster complex accompanied by liberating HCl in DMSO/EtOH mixture. …
NAID 120003020521

Enhancement of the photoluminescence of a thioamide-based pincer palladium complex in the crystalline state

Kuwabara Junpei,Ogawa Yasuyuki,Taketoshi Ayako,Kanbara Takaki,桑原純平,神原貴樹
Journal of organometallic chemistry 696(6), 1289-1293, 2011-03
… A thioamide-based pincer Pd complex, [2,6-bis(benzylaminothiocarbonyl-κS)phenyl-κC1]chloropalladium(II), was crystallized from different solvents. …
NAID 120003020519

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★リンクテーブル★

リンク元	「Ph」「フェニル」「フェニール」
拡張検索	「diphenyleneiodonium」「phenyl isothiocyanate method」「aminobiphenyl compound」