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Fusing angular rings around a benzene moiety leads to an increase in stability. The Clar structure of anthracene , for instance, has only one π-sextet but, by moving one ring into the angular position, phenanthrene is obtained, the Clar structure of which carries two circles instead of one.
Hexafluorobenzene stands somewhat aside in the perhalogenbenzenes. If a perhalogenated benzene ring were to remain planar, then geometric constraints would force adjacent halogens closer than their associated nonbonding radius. Consequently the benzene ring buckles, reducing p-orbital overlap and aromaticity to avoid the steric clash ...
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Both mechanisms are shown as follows for the ring contraction of biphenylene: The first involves a 1,2-hydrogen shift to a carbene followed by a 1,2-carbon shift on the same C-C bond but in opposite directions. The second differs from the first only by the order of the 1,2-shifts, with the 1,2-carbon shift preceding the 1,2-hydrogen shift.
The driving force for ring-opening and polymerization is strain relief. The reaction is believed to be a living polymerization due to the lack of competing reactions. Because the two benzene rings are in close proximity this cyclophane type also serves as guinea pig for photochemical dimerization reactions as illustrated by this example: [ 21 ]
In alkanes, optimum overlap of atomic orbitals is achieved at 109.5°. The most common cyclic compounds have five or six carbons in their ring. [6] Adolf von Baeyer received a Nobel Prize in 1905 for the discovery of the Baeyer strain theory, which was an explanation of the relative stabilities of cyclic molecules in 1885.
Two different resonance forms of benzene (top) combine to produce an average structure (bottom). In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected by the stabilization of conjugation alone.
Hexanitrobenzene, also known as HNB, is a nitrobenzene compound in which six nitro groups are bonded to all six positions of a central benzene ring. It is a high-density explosive compound with chemical formula C 6 N 6 O 12, obtained by oxidizing the amine group of pentanitroaniline with hydrogen peroxide in sulfuric acid.
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