Cycloheptane is a

cycloalkane In organic chemistry, the cycloalkanes (also called naphthenes, but distinct from naphthalene) are the monocyclic saturated hydrocarbons. In other words, a cycloalkane consists only of hydrogen and carbon atoms arranged in a structure containin ...

with the molecular formula C₇ H₁₄. Cycloheptane is used as a nonpolar

solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

for the

chemical industry The chemical industry comprises the companies that produce industrial chemicals. Central to the modern world economy, it converts raw materials ( oil, natural gas, air, water, metals, and minerals) into more than 70,000 different products. ...

and as an intermediate in the manufacture of chemicals and

pharmaceutical drug A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy ( pharmacotherapy) is an important part of the medical field and ...

s. It may be derived by Clemmensen reduction from cycloheptanone. Cycloheptane vapour is irritating to the eyes and may cause

respiratory depression Hypoventilation (also known as respiratory depression) occurs when ventilation is inadequate (''hypo'' meaning "below") to perform needed respiratory gas exchange. By definition it causes an increased concentration of carbon dioxide (hypercapni ...

if inhaled in large quantity.

Conformations

Cycloheptane is not a flat molecule, because that would give C-C-C bond angles much greater than the tetrahedral angle of around 109.5°. Instead it is puckered and three-dimensional. One can ask the question of what conformations would have the same angle everywhere (near 109.5°) and all bond lengths equal. If we think of an open chain of seven bonds, there are five

dihedral angle A dihedral angle is the angle between two intersecting planes or half-planes. In chemistry, it is the clockwise angle between half-planes through two sets of three atoms, having two atoms in common. In solid geometry, it is defined as the un ...

s that can be chosen, for the sequences (1,2,3,4), (2,3,4,5), and so on. The last bond though should end where the first began, and should form the correct angle with the first bond. This imposes four constraints, but we have five dihedral angles to play with, so there is one degree of freedom. It turns out that there are two continua of solutions. One is a circular series of fourteen "boat" conformations interspersed with "twist-boat" conformations, and the other is a circular series of fourteen "chair" conformations interspersed with "twist-chair" conformations. The boat and chair conformations have mirror symmetry, while the twist-boat and twist-chair have two-fold rotational symmetry. Conformations between boat and twist-boat or between chair and twist-chair have no symmetry. The passage along the continuum boat→twist-boat→boat→twist-boat→boat constitutes a pseudorotation, as does chair→twist-chair→chair→twist-chair→chair. Actually in cycloheptane the conformations will not have exactly equal bond angles and lengths everywhere, because they do not have a seven-fold rotation or improper rotation. This contrasts with the chair form of cyclohexane in which all the bond angles and lengths are equal due to symmetry. Below are depicted the boat and chair conformations. File:Cycloheptane boat conformation.svg, Boat File:Cycloheptane chair conformation.svg, Chair

References

Cycloalkanes Hydrocarbon solvents Seven-membered rings {{hydrocarbon-stub