Фенильная группа — Википедия
Фенильная группа — ВикипедияФенильная группа — Википедия
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In organic chemistry , the phenyl group or phenyl ring is a cyclic group of atoms with the formula C 6 H 5. Phenyl groups are 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 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. Benzene is sometimes denoted as PhH. Phenyl groups are generally attached to other atoms or groups. For example, triphenylmethane Ph 3 CH 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 C 6 H 5 Cl is normally called chlorobenzene , although it could be called phenyl chloride. In special and rare cases, isolated phenyl groups are detected: Although Ph and phenyl uniquely denote C 6 H 5 , substituted derivatives also are described using the phenyl terminology. 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. Phenyl compounds are derived from benzene C 6 H 6 , 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. 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. The bond lengths between carbon atoms in a phenyl group are approximately 1. In 1 H- NMR spectroscopy, protons of a phenyl group typically have chemical shifts around 7. These chemical shifts are influenced by aromatic ring current and may change depending on substituents. Phenyl groups are usually introduced using reagents that behave as sources of the phenyl anion or the phenyl cation. Electrophiles attack benzene to give phenyl derivatives:. These reactions are called electrophilic aromatic substitutions. 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 C 6 H 4 group. It is an antihistamine used to treat allergies. 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. One of the simplest phenyl-containing compounds is phenol , C 6 H 5 OH. However, a significant contribution is the greater electronegativity of the sp 2 alpha carbon in phenol compared to the sp 3 alpha carbon in aliphatic alcohols. From Wikipedia, the free encyclopedia. Phenylalanine , a common amino acid. Retrieved 3 March The Journal of Organic Chemistry. Selenol Selenonic acid Seleninic acid Selenenic acid. Isothiocyanate Phosphoramide Sulfenyl chloride Sulfonamide Thiocyanate. See also chemical classification , chemical nomenclature inorganic , organic. Retrieved from ' https: Aryl groups Phenyl compounds. Wikipedia articles with GND identifiers. Views Read Edit View history. This page was last edited on 12 October , at By using this site, you agree to the Terms of Use and Privacy Policy.
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Фенильная Группа — Википедия
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