Phenyl group
In organic chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph or Φ, the greek letter phi) is the functional group with the formula
where the six carbon atoms are arranged in a cyclic ring structure. This hydrophobic, highly-stable and aromatic hydrocarbon unit can be found in many organic compounds. It can be thought of as being derived from benzene (C6H6). In fact, in chemical literature benzene itself is sometimes denoted as PhH.
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 (pKa = 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.[1]
- Protons of a phenyl group typically have chemical shifts around 7.27 ppm in an 1H-NMR largely due to an aromatic ring current, but these values may change depending on substituents.
- Phenyl groups can also be found in polymers such as polystyrene.
- The phenyl group belongs to the aryl group of compounds.
- The phenyl group differs from the benzyl functional group in that benzyls have an extra CH2.
References
- ^ "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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