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Revision as of 07:47, 12 July 2011 editM97uzivatel (talk | contribs)Extended confirmed users6,580 edits cs:Cyklobutan← Previous edit		Latest revision as of 13:42, 30 October 2024 edit undoMondtaler (talk | contribs)182 edits GHS04 and H280 specifically address hazards linked to the pressurized storage of gases. As storage methods can vary, these pictograms and hazard statements are not universally applicable to all gaseous compounds.Tag: 2017 wikitext editor
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			{{short description|Organic compound}}
	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 415866234
			| Watchedfields = changed
	| Name = Cyclobutane
			| verifiedrevid = 439048895
	| ImageFile = Cyclobutane2.svg
			| Name = Cyclobutane
	| ImageSize = 100px
			| ImageFile = Siklobüten für Kurdi.svg
	| ImageFileL1 = Cyclobutane-buckled-3D-balls.png
	| ImageSizeL1 = 100px		| ImageSize = 100px
	| ImageNameL1 = Cyclobutane		| ImageFileL1 = Cyclobutane-buckled-3D-balls.png
	| ImageFileR1 = Cyclobutane-buckled-3D-vdW.png		| ImageNameL1 = Cyclobutane
			| ImageFileR1 = Cyclobutane-buckled-3D-vdW.png
			| ImageNameR1 = Cyclobutane
	| ImageSizeR1 = 100px
	| ImageNameR1 = Cyclobutane		| PIN = Cyclobutane
			| OtherNames = Ethene dimer<br/>Biethylene<br/>Diethylene
	| IUPACName = cyclobutane
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
			| CASNo_Ref = {{cascite|correct|EBI}}
	| CASNo = 00287-23-0
	| SMILES = C1CCC1		| CASNo = 287-23-0
			| UNII_Ref = {{fdacite|changed|FDA}}
			| UNII = 5X619RB2CY
			| SMILES = C1CCC1
			| PubChem = 9250
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID = 8894
			| EC_number = 206-014-5
			| UNNumber = 2601
			| ChEBI = 30377
			| Beilstein = 1900183
			| Gmelin = 81684
			| InChI = 1/C4H8/c1-2-4-3-1/h1-4H2
			| InChIKey = PMPVIKIVABFJJI-UHFFFAOYAP
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			| StdInChI = 1S/C4H8/c1-2-4-3-1/h1-4H2
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = PMPVIKIVABFJJI-UHFFFAOYSA-N
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>4</sub>H<sub>8		| Formula = C<sub>4</sub>H<sub>8</sub>
			| Appearance = Colorless gas
	| MolarMass = 56.107 g/mol
			| MolarMass = 56.107 g/mol
	| MeltingPtC = -91
	| BoilingPtC = 12.5		| MeltingPtC = -91
	| Density = 0.720 g/cm<sup>3</sup>		| BoilingPtC = 12.5
			| Density = 0.720 g/cm<sup>3</sup>
	}}		}}
	| Section8 = {{Chembox Related		|Section7={{Chembox Hazards
			| GHSPictograms = {{GHS02}}
			| GHSSignalWord = Danger
			| HPhrases = {{H-phrases|220}}
			| PPhrases = {{P-phrases|210|377|381|403|410+403}}
			| NFPA-H=1
			| NFPA-F=4
			| NFPA-R=0
			}}
			|Section8={{Chembox Related
	| OtherAnions =		| OtherAnions =
	| OtherCations =		| OtherCations =
	| OtherFunctn = ]		| OtherFunction = ]
	| Function = ]		| OtherFunction_label = ]
	| OtherCpds = ]; ] }}		| OtherCompounds = ]; ]; ]; ] }}
	}}		}}
	'''Cyclobutane''' is an ] with the formula (CH<sub>2</sub>)<sub>4</sub>. Cyclobutane is a colourless gas and commercially available as a ]. 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.		'''Cyclobutane''' is a ] and ] with the formula (CH<sub>2</sub>)<sub>4</sub>. Cyclobutane is a colourless gas and is commercially available as a ]. 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.<ref>{{cite book|title=The Chemistry of Cyclobutanes|editor=Zvi Rappoport, Joel F. Liebman|year=2005|isbn=9780470864029 |doi=10.1002/0470864028|publisher=John Wiley & Sons|series= PATAI'S Chemistry of Functional Groups}}</ref>
	==Structure==		==Structure==
	The bond angles between ] ]s are significantly ] and as such have lower ] than related linear or unstrained hydrocarbons, e.g. ] or ]. As such, cyclobutane is unstable above about 500 °C.		The bond angles between ] ]s are significantly ] and as such have lower ] than related linear or unstrained hydrocarbons, e.g. ] or ]. As such, cyclobutane is unstable above about 500&nbsp;°C.
	The four carbon atoms in cyclobutane are not coplanar, instead the ring typically adopts a folded or "puckered" ].<ref></ref> One of the carbon atoms makes a 25° angle with the plane formed by the other three carbons. In this way some of the ] interactions are reduced. The conformation is also known as a "butterfly". Equivalent puckered conformations interconvert:		The four carbon atoms in cyclobutane are not coplanar; instead, the ring typically adopts a folded or "puckered" ].<ref name="Encyclopedia Britannica">{{cite web | title=Cyclobutane | website=Encyclopedia Britannica | url=https://www.britannica.com/science/cyclobutane | access-date=8 July 2022}}</ref> 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 ] interactions are reduced. The conformation is also known as a "butterfly". Equivalent puckered conformations interconvert:
	:]		:]
	==Cyclobutanes in biology and biotechnology==		==Cyclobutanes in biology and biotechnology==
	:]		:]
	Despite inherent strain the cyclobutane motif is indeed found in nature. One unusual example is ''pentacycloanammoxic acid''<ref>{{cite journal		Despite the inherent strain, the cyclobutane motif is indeed found in nature. One example is pentacycloanammoxic acid,<ref>{{cite journal
	| journal = Nature		| journal = Nature
	| volume = 419		| volume = 419
	| pages = 708–712		| pages = 708–712
	| year = 2002		| year = 2002
	| doi = 10.1038/nature01128		| doi = 10.1038/nature01128
	| title = Linearly concatenated cyclobutane lipids form a dense bacterial membrane		| title = Linearly concatenated cyclobutane lipids form a dense bacterial membrane
	| author = J. S. Sinninghe Damsté, M. Strous, W. I. C. Rijpstra, E. C. Hopmans, J. A. J. Geenevasen, A. C. T. van Duin, L. A. van Niftrik and M. S. M. Jetten		| author = J. S. Sinninghe Damsté, M. Strous, W. I. C. Rijpstra, E. C. Hopmans, J. A. J. Geenevasen, A. C. T. van Duin, L. A. van Niftrik and M. S. M. Jetten
	| pmid = 12384695		| pmid = 12384695
			| issue = 6908| bibcode = 2002Natur.419..708S
	| issue = 6908}}</ref> which is a ] 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 ]process where it forms part of a tight and very dense membrane believed to protect the organism from toxic ] and ] involved in the production of nitrogen and water from ] ions and ].<ref>{{cite journal
			| s2cid = 4373854
	| title = Enantioselective Synthesis of Pentacycloanammoxic Acid
			}}</ref> which is a ] 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 ] process where it forms part of a tight and very dense membrane believed to protect the organism from toxic ] and ] involved in the production of nitrogen and water from ] ions and ].<ref>{{cite journal
	| author = Vincent Mascitti and ]
			| title = Enantioselective Synthesis of Pentacycloanammoxic Acid
	| journal = ]
			| author = Vincent Mascitti and ]
	| year = 2006
			| journal = ]
	| volume = 128
	| issue = 10		| year = 2006
	| pages = 3118		| volume = 128
	| doi = 10.1021/ja058370g		| issue = 10
			| pages = 3118–9
	| pmid = 16522072}}Authors state that mode of biosynthesis is ''quite mysterious''</ref> Some related ]s are also found in nature.{{Citation needed|date=February 2008}}
			| doi = 10.1021/ja058370g
			| pmid = 16522072}}Authors state that mode of biosynthesis is ''quite mysterious''</ref> Some related ]s are also found in nature.{{Citation needed|date=February 2008}}
	Cyclobutane photodimers ("CPD's") are formed by ]s that result in the coupling of the C=C double bonds of ].<ref>{{cite journal		Cyclobutane photo dimers (CPD) are formed by ]s that result in the coupling of the C=C double bonds of ].<ref>{{cite journal
	| journal =Science		| journal =Science
	| year = 1966		| year = 1966
	| volume = 153		| volume = 153
	| issue = 3734		| issue = 3734
	| pages = 379–386		| pages = 379–386
	| doi = 10.1126/science.153.3734.379		| doi = 10.1126/science.153.3734.379
	| title = Cyclobutane-Type Pyrimidine Dimers in Polynucleotides		| title = Cyclobutane-Type Pyrimidine Dimers in Polynucleotides
	| author = R. B. Setlow		| author = R. B. Setlow
	| pmid=5328566}}		| pmid=5328566| bibcode = 1966Sci...153..379S
			| s2cid = 11210761
			}}
	</ref><ref>{{cite web		</ref><ref>{{cite web
	| author = Expert reviews in molecular medicine		| author = Expert reviews in molecular medicine
	| title = Structure of the major UV-induced photoproducts in DNA.		| title = Structure of the major UV-induced photoproducts in DNA.
	| date = 2 December 2002		| date = 2 December 2002
	| publisher = Cambridge University Press		| publisher = Cambridge University Press
	| url = http://www-ermm.cbcu.cam.ac.uk/02005331a.pdf }}</ref><ref>{{cite book		| url = http://www-ermm.cbcu.cam.ac.uk/02005331a.pdf
			| access-date = 16 August 2009
	| title = Biochemistry
			| archive-url = https://web.archive.org/web/20050321164905/http://www-ermm.cbcu.cam.ac.uk/02005331a.pdf
	| author = Christopher Mathews and K.E. Van Holde
			| archive-date = 21 March 2005
	| edition = 2nd
			| url-status = dead
	| publisher = Benjamin Cummings Publication
			}}</ref><ref>{{cite book
	| year = 1990
	| url =		| title = Biochemistry
			| author1 = Christopher Mathews
	| isbn = 978-0805350159
			| author2 = K.E. Van Holde
	| page = 1168 }}</ref> T-T dimers ] formed in between two thymines are the most abundant of the CPD's. CPD's are readily repaired by ] enzymes. In most organisms they can also be repaired by photolyases, a light-dependent family of enzymes. ] is a genetic disease where this damage can not be repaired, resulting in skin discolouration and tumours induced by exposure to ].
			| edition = 2nd
	:]
			| publisher = Benjamin Cummings Publication
			| year = 1990
			| isbn = 978-0-8053-5015-9
			| page =
			| url-access = registration
			| url = https://archive.org/details/biochemistry00math_0/page/1168
			}}</ref> ] (T-T dimers) formed in between two thymines are the most abundant of the CPDs. CPDs are readily repaired by ] enzymes. In most organisms, they can also be repaired by photolyases, a light-dependent family of enzymes. ] is a genetic disease where this damage can not be repaired, resulting in skin discolouration and tumours induced by exposure to ].
			:]
	] is a popular anticancer drug that is derived from cyclobutane-1,1-carboxylic acid.		] is a popular ] that is derived from cyclobutane-1,1-dicarboxylic acid.
	==Preparation==		==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.		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 ] by hydrogenating cyclobutene in the presence of nickel.<ref>{{cite journal|author=Richard Willstätter |author2= James Bruce |year=1907|title=Zur Kenntnis der Cyclobutanreihe|trans-title=On our knowledge of the cyclobutane series|journal=Berichte der Deutschen Chemischen Gesellschaft|volume=40|issue=4|pages= 3979–3999|doi=10.1002/cber.19070400407|url= https://zenodo.org/record/1426251 }}</ref>
	==See also==		==See also==
	{{Commons category|Cyclobutane}}
	* ]		* ]
			* ]
	==References==		==References==
	{{reflist}}		{{reflist|30em}}
	==External links==		==External links==
			{{Commons category|Cyclobutane}}
	* Datasheet
			* Datasheet
	{{cycloalkanes}}		{{cycloalkanes}}
			{{Authority control}}
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