Seven Easy Rules Of Cyclohexane Chair | Cyclohexane Chair

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Chemists accept fabricated the all-cis isomer of 1,2,3,4,5,6-hexafluorocyclohexane, a apparent arena atom with all six fluorines pointing “up” and all six hydrogens pointing “down.” This admixture is arresting for actuality the best arctic nonionic admixture now accepted to exist, according to David O’Hagan of the University of St. Andrews, in Scotland. O’Hagan, whose aggregation actinic the compound, declared the allure abaft the atom this anniversary during a Division of Fluorine Allure appointment at the American Chemical Society civic affair in Denver.

The deceptively simple atom is in absoluteness a circuitous constructed ambition because it has nine accessible isomers that can accept up to 15 conformations, O’Hagan said. Orienting all the fluorine atoms on one face of the arena in the all-cis isomer was a accurate claiming because the fluorines all appetite to repel anniversary other—the all-cis isomer has alert the ache activity as any added isomer.

O’Hagan’s lab ahead able the “four up-two down” isomer in 2012, starting from benzene and application a aggregate of oxidation, fluorination, and deoxyfluorination steps. To accomplish the “six up” isomer, O’Hagan, Neil S. Keddie, and colleagues devised a agnate action starting from myo-inositol, a cyclohexane with a hydroxyl accumulation on anniversary arena carbon.

The new molecule, which adopts the archetypal armchair anatomy of cyclohexane, is electropositive on the hydrogen face of the arena and awful electronegative on the fluorine face, arch to a dipole moment of 6.2 debyes. Many ionic compounds accept college dipole moments, but the O’Hagan team’s chase for a added arctic aliphatic or ambrosial admixture came up empty.

The aerial polarity makes fluorinated cyclohexanes acquiescent to stacking calm in layers to adapt abstracts such as aqueous crystals, O’Hagan said. Benzene and hexafluorobenzene are accepted to assemblage calm in alternating layers, he notes, and it appears the all-cis hexafluorocyclohexane provides a admixture of that adjustment aural a distinct ring.

“O’Hagan and coworkers’ alertness of the facially polarized hexafluorocyclohexane is an absorbing constructed achievement,” said Stephen G. DiMagno, an able in arctic berserk furnishings at the University of Nebraska, Lincoln. “The artificial stereoisomer demonstrates, in one abridged X-ray clear snapshot, that the dipolar C–F band of fluorocarbons will acquisition any anemic favorable electrostatic alternation in alternative to alternation with addition C–F bond.”

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