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It was introduced in 1972 by the Austrian organic chemist Erich Clar in his book The Aromatic Sextet. The rule states that given a polycyclic aromatic hydrocarbon, the resonance structure most important to characterize its properties is that with the largest number of aromatic π-sextets i.e. benzene-like moieties. [1]
The best-known example is benzene (C 6 H 6) with a conjugated system of six π electrons, which equals 4n + 2 for n = 1. The molecule undergoes substitution reactions which preserve the six π electron system rather than addition reactions which would destroy it. The stability of this π electron system is referred to as aromaticity. Still, in ...
*** Benzene is a carcinogen (cancer-causing agent). *** Very flammable. The pure material, and any solutions containing it, constitute a fire risk. Safe handling: Benzene should NOT be used at all unless no safer alternatives are available. If benzene must be used in an experiment, it should be handled at all stages in a fume cupboard.
Prismane or 'Ladenburg benzene' is a polycyclic hydrocarbon with the formula C 6 H 6. It is an isomer of benzene , specifically a valence isomer . Prismane is far less stable than benzene.
Some were originally proposed for benzene itself before the actual structure of benzene was known. Others were later synthesized in lab. Some have been observed to isomerize to benzene, whereas others tend to undergo other reactions instead, or isomerize by ways other than pericyclic reactions. Some known valence isomers of benzene
Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon. Benzene is a colorless and highly flammable liquid with a sweet smell, and is partially responsible for the aroma of gasoline.
Print/export Download as PDF; Printable version; In other projects Wikidata item; Appearance. move to sidebar hide ... Benzene: 0.87 80.1 2.65 5.5 –5.12
There is evidence that it has two isomeric forms of comparable stability (trans, cis, trans, cis, trans, trans, cis- with four interior hydrogens (shown in the infobox) and trans, cis, trans, cis, trans, cis, cis-with three interior hydrogens) which rapidly interconvert at room temperature but can be observed at low temperature by NMR. [3]