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Revision as of 18:28, 17 May 2011 editFree Bear (talk | contribs)Extended confirmed users, Rollbackers4,169 editsm Reverted edits by 119.152.27.175 (talk) to last revision by MystBot (HG)← Previous edit		Latest revision as of 17:31, 20 August 2024 edit undoSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers75,010 edits It is classified as a borane and more specifically a boron hydride cluster.
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	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 408023820		| verifiedrevid = 429598903
	| Name = '''Decaborane'''
	| ImageFile = Decaborane-3D-balls.png		| Name = Decaborane
			| ImageFile = Decaborane(14)-from-xtal-view-1-tilt-3D-bs-17.png
	| ImageSize = 200px
	| ImageName = The three-dimensional structure of decaborane		| ImageSize =
			| ImageName = The three-dimensional structure of decaborane
	| OtherNames = decaborane<br/>decaboron tetradecahydride		| ImageFile1 = Decaborane.png
			| OtherNames = decaborane<br/>decaboron tetradecahydride
	| Section1 = {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
	| ChemSpiderID = 21241886		| ChemSpiderID = 21241886
			| PubChem = 6328162
	| SMILES = 123415627839(4)71285364531192214(5)2		| SMILES = 123415627839(4)71285364531192214(5)2
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| InChI=1/B10H14/c11-5-1-2-3(1,5)7(2,9(3,5,11)13-7)8(2)4(1,2)6(1,5)10(4,8,12-6)14-8/h1-10H		| InChI =1/B10H14/c11-5-1-2-3(1,5)7(2,9(3,5,11)13-7)8(2)4(1,2)6(1,5)10(4,8,12-6)14-8/h1-10H
	| InChIKey = XAMMYYSPUSIWAS-UHFFFAOYAD		| InChIKey = XAMMYYSPUSIWAS-UHFFFAOYAD
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
Line 17:		Line 20:
	| StdInChIKey = XAMMYYSPUSIWAS-UHFFFAOYSA-N		| StdInChIKey = XAMMYYSPUSIWAS-UHFFFAOYSA-N
	| CASNo = 17702-41-9		| CASNo = 17702-41-9
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 4O04290A2J
	| EINECS = 241-711-8		| EINECS = 241-711-8
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
	| MolarMass = 122.22 g/mol		| B = 10 | H = 14
			| MolarMass = 122.22 g/mol
	| Appearance = White crystals		| Appearance = White crystals
			| Odor = bitter, ]-like or burnt ]<ref name=PGCH/>
	| Solvent = other solvents		| Solvent = other solvents
	| SolubleOther = Slightly, in cold water.		| SolubleOther = Slightly, in cold water.
	| MeltingPt = 99.6 °C
	| BoilingPt = 213 °C		| MeltingPtC = 97-98
			| BoilingPtC = 213
			| VaporPressure = 0.2 mmHg<ref name=PGCH/>
			| Density = 0.94 g/cm<sup>3</sup><ref name=PGCH/>
	}}		}}
	| Section7 = {{Chembox Hazards		| Section7 = {{Chembox Hazards
	| Autoignition = 149 °C}}		| AutoignitionPtC = 149
			| AutoignitionPt_notes =
			| PEL = TWA 0.3 mg/m<sup>3</sup> (0.05 ppm) <ref name=PGCH>{{PGCH|0175}}</ref>
			| FlashPtF = 176<ref name=PGCH/>
			| IDLH = 15 mg/m<sup>3</sup><ref name=PGCH/>
			| REL = TWA 0.3 mg/m<sup>3</sup> (0.05 ppm) ST 0.9 mg/m<sup>3</sup> (0.15 ppm) <ref name=PGCH/>
			| MainHazards = may ignite spontaneously on exposure to air<ref name=PGCH/>
			| LC50 = 276 mg/m<sup>3</sup> (rat, 4 hr)<br/>72 mg/m<sup>3</sup> (mouse, 4 hr)<br/>144 mg/m<sup>3</sup> (mouse, 4 hr)<ref>{{IDLH|17702419|Decaborane}}</ref>
			| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS08}}
			| GHSSignalWord = Danger
			| HPhrases = {{H-phrases|228|301|310|316|320|330|335|336|370|372}}
			| PPhrases = {{P-phrases|210|240|241|260|261|262|264|270|271|280|284|301+310|302+350|304+340|305+351+338|307+311|310|312|314|320|321|322|330|332+313|337+313|361|363|370+378|403+233|405|501}}
			| NFPA-H = 3
			| NFPA-F = 2
			| NFPA-R = 2
			| NFPA-S = W
	}}		}}
			}}
	'''Decaborane''', also called '''decaborane(14)''', is the ] with the ] ]<sub>10</sub>]<sub>14</sub>. This white crystalline compound is one of the principal boron hydride clusters, both as a reference structure and as a precursor to other boron hydrides.		'''Decaborane''', also called '''decaborane(14)''', is the ] with the ] ]<sub>10</sub>]<sub>14</sub>. It is classified as a ] and more specifically a ]. This white crystalline compound is one of the principal boron hydride clusters, both as a reference structure and as a precursor to other boron hydrides. It is toxic and volatile, giving off a foul odor, like that of burnt rubber or chocolate.
	==Handling properties and structure==		==Handling, properties and structure==
	B<sub>10</sub>H<sub>14</sub> possesses a strong characteristic odor, sometimes described as musty or intensely bitter, chocolate-like that is unique to ]s. The physical characteristics of decaborane(14) resemble those of the organic compounds, such as ] and ], in that it can be sublimed under vacuum at moderate temperatures. ] is the common method of purification. Like organic compounds, decaborane is highly flammable, but, like other ]s, it burns with a bright green flame. It is not sensitive to moist air, although it hydrolyzes in boiling water, releasing hydrogen and giving a solution of ]. It is soluble in cold water as well as a variety of non-polar and moderately polar ]s.		The physical characteristics of decaborane(14) resemble those of ] and ], all three of which are volatile colorless solids. ] is the common method of purification. Decaborane is highly flammable, and burns with a bright green flame like other ]. It is not sensitive to moist air, although it hydrolyzes in boiling water, releasing hydrogen and giving a solution of ]. It is soluble in cold water as well as a variety of non-polar and moderately polar ]s.<ref name=IS/>
	In decaborane, the B<sub>10</sub> framework resembles an incomplete ]. Each boron has one "radial" hydride, and four boron atoms near the open part of the cluster feature extra hydrides. In the language of cluster chemistry, the structure is classified as "nido".		In decaborane, the B<sub>10</sub> framework resembles an incomplete ]. Each boron has one "radial" hydride, and four boron atoms near the open part of the cluster feature extra hydrides. In the language of cluster chemistry, the structure is classified as "nido".
	==Synthesis and reactions==		==Synthesis and reactions==
	It is commonly synthesized via the ] of smaller boron hydride ]. For example, heating ] or ] gives decaborane, with loss of H<sub>2</sub>.<ref>Greenwood, N. N.; & Earnshaw, A. (1997). Chemistry of the Elements (2nd Edn.), Oxford:Butterworth-Heinemann. ISBN 0-7506-3365-4.</ref>		It is commonly synthesized via the ] of smaller boron hydride ]. For example, pyrolysis of ] or ] gives decaborane, with loss of H<sub>2</sub>.<ref>{{Greenwood&Earnshaw}}</ref> On a laboratory scale, sodium borohydride is treated with boron trifluoride to give NaB<sub>11</sub>H<sub>14</sub>, which is acidified to release borane and hydrogen gas.<ref name=IS>Gary B. Dunks, Kathy Palmer-Ordonez, Eddie Hedaya "Decaborane(14)" Inorg. Synth. 1983, vol. 22, pp. 202–207. {{doi|10.1002/9780470132531.ch46}}</ref>
			It reacts with Lewis bases (L) such as ] and ], to form adducts:<ref name=LJT>{{cite book|title=Inorganic Syntheses|author=Charles R. Kutal |author2=David A. Owen |author3=Lee J. Todd |chapter=''closo'' -1,2-Dicarbadodecaborane(12): &#91; ''1,2-Dicarbaclovododecaborane(12'' )&#93; |year=1968 |volume=11|pages=19–24|doi=10.1002/9780470132425.ch5|isbn=978-0-470-13170-1 }}</ref><ref name=MFH>{{cite book|chapter=Icosahedral Carboranes and Intermediates Leading to the Preparation of Carbametallic Boron Hydride Derivatives |author=M. Frederick Hawthorne |author2=Timothy D. Andrews |author3=Philip M. Garrett |author4=Fred P. Olsen |author5=Marten Reintjes |author6=Fred N. Tebbe |author7=Les F. Warren |author8=Patrick A. Wegner |author9=Donald C. Young |title=Inorganic Syntheses|year=1967 |volume=10|pages=91–118|doi=10.1002/9780470132418.ch17|isbn=978-0-470-13241-8}}</ref>
	It reacts with Lewis bases (L) such as ] and ], to form derivatives with the formula B<sub>10</sub>H<sub>12</sub>·2L.
	:B<sub>10</sub>H<sub>14</sub> + 2 L → B<sub>10</sub>H<sub>12</sub>L<sub>2</sub> + H<sub>2</sub>		:B<sub>10</sub>H<sub>14</sub> + 2 L → B<sub>10</sub>H<sub>12</sub>L<sub>2</sub> + H<sub>2</sub>
	These species, which are classified as "arachno" clusters, in turn react with ] to give the "closo" ortho-]:		These species, which are classified as "arachno" clusters, in turn react with ] to give the "closo" ]:
	:B<sub>10</sub>H<sub>12</sub>·2L + C<sub>2</sub>H<sub>2</sub> → C<sub>2</sub>B<sub>10</sub>H<sub>12</sub> + 2 L + H<sub>2</sub>		:B<sub>10</sub>H<sub>12</sub>·2L + C<sub>2</sub>H<sub>2</sub> → C<sub>2</sub>B<sub>10</sub>H<sub>12</sub> + 2 L + H<sub>2</sub>
	It is a weak ]. Monodeprotonation generates the ] <sup>−</sup>, with again a nido structure.		Decaborane(14) is a weak ]. Monodeprotonation generates the ] <sup>−</sup>, with again a nido structure.
			In the ], decaborane is converted to arachno-CB<sub>9</sub>H<sub>14</sub><sup>−</sup>:
	==Applications==
			:B<sub>10</sub>H<sub>14</sub> + CH<sub>2</sub>O + 2 OH<sup>−</sup> + H<sub>2</sub>O → CB<sub>9</sub>H<sub>14</sub><sup>−</sup> + B(OH)<sub>4</sub><sup>−</sup> + H<sub>2</sub>
	Decaborane has no significant applications, although it has often been investigated. Since the molecule decomposes in a plasma, yielding monoatomic boron ions, decaborane is potentially useful as a fuel for ],<ref></ref> and for low energy ] of boron in the manufacture of ]s. It has also been considered for ]-assisted ] for the manufacture boron-containing ]s. In fusion research, the ]-absorbing nature of boron has led to the use of these thin boron-rich films to "boronize" the walls of the ] vacuum vessel to reduce recycling of particles and impurities into the plasma and improve overall performance.<ref> 15th PSI Gifu</ref>
			==Possible applications==
	Decaborane was also developed as an additive to special high-performance ]s. Its derivates were investigated as well, e.g. ]. One patented fuel composition included ]-] ]. Vinyl decaborane ("dekene") is prepared by reacting decaborane with ].<ref>{{cite web | url = http://www.freepatentsonline.com/3967989.html | title = High energy propellant compositions including vinyl decaborane-polyester copolymer binder (United States Patent 3967989) | accessdate = 2009-09-25 | publisher = US Patent Office | author = Hawthorne, Marion F. | year = 1976 }}</ref>
			Decaborane has no significant commercial applications, although the compound has often been investigated. It and its derivatives were investigated as an additive to special high-performance ]s. Its derivates were investigated as well, e.g. ethyl decaborane.{{cn|date=May 2024}}
			Decaborane is an effective reagent for the ] of ketones and aldehydes.<ref>{{cite journal|author1=Jong Woo Bae|author2=Seung Hwan Lee|author3=Young Jin Cho|author4= Cheol Min Yoon|journal=J. Chem. Soc., Perkin Trans. 1|year=2000|pages=145–146|title=A reductive amination of carbonyls with amines using decaborane in methanol|issue=2|doi=10.1039/A909506C}}</ref>
			Decaborane has been assessed for low energy ] of boron in the manufacture of ]s. It has also been considered for ]-assisted ] for the manufacture of boron-containing ]s. In fusion research, the ]-absorbing nature of boron has led to the use of these thin boron-rich films to "boronize" the walls of the ] vacuum vessel to reduce recycling of particles and impurities into the plasma and improve overall performance.<ref>{{cite web |url=http://www.nifs.ac.jp/psi/abstract/p1-05.html |archive-url=https://web.archive.org/web/20040530120541/http://www.nifs.ac.jp/psi/abstract/p1-05.html |archive-date=2004-05-30 |author1=Nakano, T. |author2=Higashijima, S. |author3=Kubo, H. |author4=Yagyu, J. |author5=Arai, T. |author6=Asakura, N. |author7=Itami, K. |title=Boronization effects using deuterated-decaborane (B<sub>10</sub>D<sub>14</sub>) in JT-60U |work=15th PSI Gifu, P1-05 |publisher=National Institute for Fusion Science |location=Sokendai, Japan }}</ref> It has been evaluated in the context of ].<ref>{{Cite news|url=https://www.nextbigfuture.com/2018/03/lpp-fusion-has-funds-try-to-reach-nuclear-fusion-net-gain-milestone.html|title=LPP Fusion has funds try to reach nuclear fusion net gain milestone {{!}} NextBigFuture.com|last=Wang|first=Brian|date=2018-03-27|work=NextBigFuture.com|access-date=2018-03-27|language=en-US}}</ref>
	==Safety==		==Safety==
	Decaborane, like ], is a powerful toxin affecting ], although decaborane is less toxic than pentaborane. It can be absorbed through skin. It forms an explosive mixture with ], which caused an often quoted explosion in a ] manufacturing facility in 1948 when CCl<sub>4</sub> was used to clean the equipment.<ref>], , accessed 23 Oct 2006.</ref>		Decaborane, like ], is a powerful toxin affecting the ], although decaborane is less toxic than pentaborane. It can be absorbed through skin.
			Purification by sublimation require a dynamic vacuum to remove evolved gases. Crude samples explode near 100&nbsp;°C.<ref name=MFH/>
			It forms an explosive mixture with ], which caused an often-mentioned explosion in a manufacturing facility.<ref>{{ cite web | publisher = ] | url = http://www.chem.ucla.edu/dept/Faculty/hawthorne/lecture/lecture2.htm | title = Condensed version of the 79th Faculty Research Lecture Presented by Professor M. Frederick Hawthorne }}</ref>
			In crystalline form, it reacts violently with ] and ] which has a use as rocket fuel oxidizer, producing an extremely powerful detonation.<ref>{{cite web |quote=YouTube video name: 'The Most DESTRUCTIVE Chemical Reaction from two NON-explosive components' |title= The Most DESTRUCTIVE Chemical Reaction from two NON-explosive components |website= ] |date=21 December 2023 |url=https://www.youtube.com/watch?v=DnOQsC9MGbc }}</ref>
	==References==		==References==
	{{reflist|2}}		{{reflist}}
	==Further reading==		==Further reading==
	* NIST Chemistry Webbook, , accessed 23 October 2006.		* {{ cite web | publisher = NIST | work = WebBook | title = Decaborane(14) | url = http://webbook.nist.gov/cgi/cbook.cgi?ID=17702-41-9&Units=SI }}
	* National Pollutant Inventory, , accessed 23 October 2006.		* {{ cite web | work = National Pollutant Inventory | url = http://www.npi.gov.au/substances/boron/index.html | title = Boron and Compounds | publisher = Australian Government }}
	*		* {{ cite web | url = https://www.organic-chemistry.org/chemicals/reductions/decaborane.shtm | title = Decaborane | publisher = Organic Chemistry Portal }}
	* ], , accessed 23 October 2006.		* {{ cite web | publisher = WebElements | url = http://www.webelements.com/compounds/boron/decaborane_14.html | title = Boron compounds: decaborane (14) }}
			* {{cite web | publisher = Centers for Disease Control and Prevention | url = https://www.cdc.gov/niosh/npg/npgd0175.html | title = NIOSH Pocket Guide to Chemical Hazards - Decaborane }}
			{{boron compounds}}
			{{Hydrides by group}}
	]		]
	]		]
			]
	]
	]
	]
	]
	]
	]
	]
	]