Editing Cyclohexane conformation (section)

===Boat and twist-boat conformations===
The boat conformations have higher energy than the chair conformations. The interaction between the two '''flagpole''' hydrogens, in particular, generates [[steric strain]]. Torsional strain also exists between the C2–C3 and C5–C6 bonds (carbon number 1 is one of the two on a mirror plane), which are [[eclipsed]] — that is, these two bonds are parallel one to the other across a mirror plane. Because of this strain, the boat configuration is unstable (i.e. is not a local energy minimum).

The [[molecular symmetry]] is ''C''<sub>2v</sub>.

The boat conformations spontaneously distorts to twist-boat conformations.  Here the [[Symmetry group|symmetry]] is ''D''<sub>2</sub>, a purely rotational point group with three twofold axes. This conformation can be derived from the boat conformation by applying a slight twist to the molecule so as to remove eclipsing of two pairs of methylene groups. The twist-boat conformation is chiral, existing in right-handed and left-handed versions.

The concentration of the twist-boat conformation at room temperature is less than 0.1%, but at {{convert|1073|K|C|0}} it can reach 30%. Rapid cooling of a sample of cyclohexane from {{convert|1073|K|C|0}} to {{convert|40|K|C|0}} will freeze in a large concentration of twist-boat conformation, which will then slowly convert to the chair conformation upon heating.<ref>{{Cite journal|title = Spectroscopic detection of the twist-boat conformation of cyclohexane. Direct measurement of the free energy difference between the chair and the twist-boat|journal = [[J. Am. Chem. Soc.]]|date = 1975-05-01|pages = 3244–3246|volume = 97|issue = 11|doi = 10.1021/ja00844a068|first1 = M.|last1 = Squillacote|first2 = R. S.|last2 = Sheridan|first3 = O. L.|last3 = Chapman|first4 = F. A. L.|last4 = Anet| bibcode=1975JAChS..97.3244S }}</ref>