Hubbry Logo
logo
Polycyclic aromatic hydrocarbon
Community hub

Polycyclic aromatic hydrocarbon

logo
0 subscribers
Be the first to start a discussion here.
Be the first to start a discussion here.
Contribute something to knowledge base
Hub AI

Polycyclic aromatic hydrocarbon AI simulator

(@Polycyclic aromatic hydrocarbon_simulator)

Polycyclic aromatic hydrocarbon

A polycyclic aromatic hydrocarbon (PAH) is any member of a class of organic compounds that is composed of multiple fused aromatic rings. Most are produced by the incomplete combustion of organic matter—by engine exhaust fumes, tobacco, incinerators, in roasted meats and cereals, or when biomass burns at lower temperatures as in forest fires. The simplest representative is naphthalene, having two aromatic rings, and the three-ring compounds anthracene and phenanthrene. PAHs are uncharged, non-polar and planar. Many are colorless. Many of them are also found in fossil fuel deposits such as coal and in petroleum. Exposure to PAHs can lead to different types of cancer, to fetal development complications, and to cardiovascular issues.[medical citation needed]

Polycyclic aromatic hydrocarbons are discussed as possible starting materials for abiotic syntheses of materials required by the earliest forms of life.

The terms polyaromatic hydrocarbon, or polynuclear aromatic hydrocarbon (abbreviated as PNA) are also used for this concept.

By definition, polycyclic aromatic hydrocarbons have multiple aromatic rings, precluding benzene from being considered a PAH. Sources such as the US EPA and CDC consider naphthalene to be the simplest PAH. Most authors exclude compounds that include heteroatoms in the rings, or carry substituents.

A polyaromatic hydrocarbon may have rings of various sizes, including some that are not aromatic. Those that have only six-membered rings are said to be alternant.

The following are examples of PAHs that vary in the number and arrangement of their rings:

Most PAHs, like naphthalene, anthracene, and coronene, are planar. This geometry is a consequence of the fact that the σ-bonds that result from the merger of sp2 hybrid orbitals of adjacent carbons lie on the same plane as the carbon atom. Those compounds are achiral, since the plane of the molecule is a symmetry plane.

In rare cases, PAHs are not planar. In some cases, the non-planarity may be forced by the topology of the molecule and the stiffness (in length and angle) of the carbon-carbon bonds. For example, unlike coronene, corannulene adopts a bowl shape in order to reduce the bond stress. The two possible configurations, concave and convex, are separated by a relatively low energy barrier (about 11 kcal/mol).

See all
hydrocarbons composed of multiple aromatic rings
User Avatar
No comments yet.