Cyclobutane 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 ...

and

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

with the formula (CH₂)₄. Cyclobutane is a colourless gas and commercially available as a

liquefied gas Liquefied gas (sometimes referred to as liquid gas) is a gas that has been turned into a liquid by cooling or compressing it. Examples of liquefied gases include liquid air, liquefied natural gas, and liquefied petroleum gas. Liquid air At the ...

. Derivatives of cyclobutane are called cyclobutanes. Cyclobutane itself is of no commercial or biological significance, but more complex derivatives are important in biology and biotechnology.

Structure

The bond angles between

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon makes ...

atom Every atom is composed of a nucleus and one or more electrons bound to the nucleus. The nucleus is made of one or more protons and a number of neutrons. Only the most common variety of hydrogen has no neutrons. Every solid, liquid, gas ...

s are significantly strained and as such have lower bond energies than related linear or unstrained hydrocarbons, e.g.

butane Butane () or ''n''-butane is an alkane with the formula C4H10. Butane is a gas at room temperature and atmospheric pressure. Butane is a highly flammable, colorless, easily liquefied gas that quickly vaporizes at room temperature. The name bu ...

cyclohexane Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colorless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohex ...

. As such, cyclobutane is unstable above about 500 °C. The four carbon atoms in cyclobutane are not coplanar; instead the ring typically adopts a folded or "puckered" conformation. This implies that the C-C-C angle is less than 90°. One of the carbon atoms makes a 25° angle with the plane formed by the other three carbons. In this way some of the eclipsing interactions are reduced. The conformation is also known as a "butterfly". Equivalent puckered conformations interconvert: : CyclobutaneConf2

Cyclobutanes in biology and biotechnology

Despite inherent strain the cyclobutane motif is indeed found in nature. One unusual example is ''pentacycloanammoxic acid'', which is a ladderane composed of 5 fused cyclobutane units. The estimated strain in this compound is 3 times that of cyclobutane. The compound is found in bacteria performing the

anammox Anammox, an abbreviation for anaerobic ammonium oxidation, is a globally important microbial process of the nitrogen cycle that takes place in many natural environments. The bacteria mediating this process were identified in 1999, and were a grea ...

process where it forms part of a tight and very dense membrane believed to protect the organism from toxic hydroxylamine and

hydrazine Hydrazine is an inorganic compound with the chemical formula . It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly toxic unless handled in solution as, for example, hydrazin ...

involved in the production of nitrogen and water from

nitrite The nitrite ion has the chemical formula . Nitrite (mostly sodium nitrite) is widely used throughout chemical and pharmaceutical industries. The nitrite anion is a pervasive intermediate in the nitrogen cycle in nature. The name nitrite also re ...

ions and

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogeno ...

. Some related fenestranes are also found in nature. Cyclobutane photodimers (CPD) are formed by photochemical reactions that result in the coupling of the C=C double bonds of pyrimidines. Thymine dimers (T-T dimers) formed in between two thymines are the most abundant of the CPDs. CPDs are readily repaired by

nucleotide excision repair Nucleotide excision repair is a DNA repair mechanism. DNA damage occurs constantly because of chemicals (e.g. intercalating agents), radiation and other mutagens. Three excision repair pathways exist to repair single stranded DNA damage: Nucle ...

enzymes. In most organisms they can also be repaired by photolyases, a light-dependent family of enzymes.

Xeroderma pigmentosum Xeroderma pigmentosum (XP) is a genetic disorder in which there is a decreased ability to repair DNA damage such as that caused by ultraviolet (UV) light. Symptoms may include a severe sunburn after only a few minutes in the sun, freckling in s ...

is a genetic disease where this damage can not be repaired, resulting in skin discolouration and tumours induced by exposure to UV light. : Thymine photodimer

Carboplatin Carboplatin, sold under the trade name Paraplatin among others, is a chemotherapy medication used to treat a number of forms of cancer. This includes ovarian cancer, lung cancer, head and neck cancer, brain cancer, and neuroblastoma. It is used ...

is a popular anticancer drug that is derived from cyclobutane-1,1-dicarboxylic acid.

Preparation

Many methods exist for the preparation of cyclobutanes. Alkenes dimerize upon irradiation with UV-light. 1,4-Dihalobutanes convert to cyclobutanes upon dehalogenation with reducing metals. Cyclobutane was first synthesized in 1907 by James Bruce and Richard Willstätter by hydrogenating cyclobutene in the presence of nickel.

References

External links

* Datashee
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{{Authority control Cycloalkanes Cyclobutanes

Structure

Cyclobutanes in biology and biotechnology

Preparation

See also

References

External links