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The most energetically favorable conformation for a monosubstituted cyclohexane is the chair conformation with the non-hydrogen substituent in the equatorial position because it prevents high steric strain from 1,3 diaxial interactions. [10] In methylcyclohexane the two chair conformers are not isoenergetic. The methyl group prefers the ...
While simple molecules can be described by these types of conformations, more complex molecules require the use of the Klyne–Prelog system to describe the different conformers. [6] More specific examples of conformations are detailed elsewhere: Ring conformation Cyclohexane conformations, including with chair and boat conformations among others.
As a consequence of the chair flip, the axially-substituted and equatorially-substituted conformers of a molecule like chlorocyclohexane cannot be isolated at room temperature. However, in some cases, the isolation of individual conformers of substituted cyclohexane derivatives has been achieved at low temperatures (–150 °C).
The chair conformation of six-membered rings have a dihedral angle of 60° between adjacent substituents thus usually making it the most stable conformer. Since there are two possible chair conformation steric and stereoelectronic effects such as the anomeric effect, 1,3-diaxial interactions, dipoles and intramolecular hydrogen bonding must be taken into consideration when looking at relative ...
The chair and twist-boat are energy minima and are therefore conformers, while the half-chair and the boat are transition states and represent energy maxima. The idea that the chair conformation is the most stable structure for cyclohexane was first proposed as early as 1890 by Hermann Sachse, but only gained widespread acceptance much later.
The ratio K2/K1 can be related directly to the strain energy difference between the conformers C1 and C2; if it is small higher concentrations of A will directly bind to C2 and make the effector E inefficient. In addition, the response time of such allosteric switches depends on the strain of the conformer interconversion transitions state. [15]
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Hendrickson noted that "cyclooctane is unquestionably the conformationally most complex cycloalkane owing to the existence of many conformers of comparable energy". The boat-chair conformation (below) is the most stable form. [4] This conformation was confirmed by Allinger and co-workers. [5] The crown conformation (below) [6] is slightly less ...