Naphthalene

related topics
{acid, form, water}
{disease, patient, cell}
{specie, animal, plant}
{land, century, early}
{@card@, make, design}
{woman, child, man}
{household, population, female}
{math, energy, light}

80.26 °C, 353 K, 176 °F

218 °C, 491 K, 424 °F

Naphthalene, also known as naphthalin, bicyclo[4.4.0]deca-1,3,5,7,9-pentene or antimite is a crystalline, aromatic, white, solid hydrocarbon with formula C10H8 and the structure of two fused benzene rings. It is best known as the traditional, primary ingredient of mothballs. It is volatile, forming a flammable vapor, and readily sublimes at room temperature, producing a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass.[1]

Contents

History

In 1819–1820, at least two chemists reported a white solid with a pungent odor derived from the distillation of coal tar. In 1821, John Kidd described many of this substance's properties and the means of its production, and proposed the name naphthaline, as it had been derived from a kind of naphtha (a broad term encompassing any volatile, flammable liquid hydrocarbon mixture, including coal tar).[2] Naphthaline's chemical formula was determined by Michael Faraday in 1826. The structure of two fused benzene rings was proposed by Emil Erlenmeyer in 1866,[3] and confirmed by Carl Gräbe three years later.

Structure and reactivity

A naphthalene molecule is derived by the fusion of a pair of benzene rings. (In organic chemistry, rings are fused if they share two or more atoms.) Accordingly, naphthalene is classified as a benzenoid polycyclic aromatic hydrocarbon (PAH). There are two sets of equivalent hydrogen atoms: the alpha positions are positions 1, 4, 5, and 8 on the drawing below, and the beta positions are positions 2, 3, 6, and 7.

Full article ▸

related documents
Solvent
Base (chemistry)
Hydrolysis
Chemical engineering
RNA
Stoma
Sulfur dioxide
Integrin
Endomembrane system
Thorium
Acid
Complex (chemistry)
Ubiquitin
Tetra-ethyl lead
Ether
Glass transition temperature
Osmium tetroxide
Molybdenum
Electrolysis
Materials science
Fluorocarbon
Neutron activation analysis
Primary structure
Protein folding
Disulfide bond
Miller-Urey experiment
Tritium
Manganese
Nitrogen cycle
Agarose gel electrophoresis