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The chair conformation is the most stable conformer. At 298 K (25 °C), 99.99% of all molecules in a cyclohexane solution adopt this conformation. The C–C ring of the chair conformation has the same shape as the 6-membered rings in the diamond cubic lattice. [7]: 16 This can be modeled as follows.
Substituents on a cyclohexane ring prefer to reside in the equatorial position to the axial. The difference in Gibbs free energy (ΔG) between the higher energy conformation (axial substitution) and the lower energy conformation (equatorial substitution) is the A-value for that particular substituent.
The chair conformation minimizes both angle strain and torsional strain by having all carbon-carbon bonds at 110.9° and all hydrogens staggered from one another. [2] The conformational changes that occur in a cyclohexane ring flip take place over several stages. Structure D (10.8 kcal/mol) is the highest energy transition state of the process.
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.
A cyclohexane molecule in the chair conformation. Axial hydrogen are shown as red while orbital hydrogen are blue. Axial hydrogen are shown as red while orbital hydrogen are blue. A very simple picture, but very large and very clear, it adds immensely to the value of its article, so I'd like to nominate it for Valued Picture
In addition, cyclohexane conformations can be used to indicate if the molecule has any 1,3 diaxial-interactions which are steric interactions between axial substituents on the 1,3, and 5 carbons. [8] Chair conformation of beta-D-Glucose The cyclohexane conformations in relation to the potential energy at each conformation
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cyclohexane chair conformation: D 4d: E 2S 8 2C 4 2S 8 3 C 2 4C 2 ' 4σ d: 45° twist sulfur (crown conformation of S 8) dimanganese decacarbonyl (staggered rotamer) octafluoroxenate ion (idealized geometry) D 5d: E 2C 5 2C 5 2 5C 2 i 2S 10 3 2S 10 5σ d: 36° twist ferrocene (staggered rotamer) Ruthenocene (stag) fulleride ion: S 4: E 2S 4 C 2 ...