Pentamethylbismuth

Pentamethylbismuth
Names


Preferred IUPAC name Pentamethyl-λ⁵-bismuthane
Identifiers
CAS Number	148739-67-7^Y^[1]
3D model (JSmol)	Interactive image
PubChem CID	21933141
UNII	MYP8RT4JE2^Y
InChI InChI=1S/5CH3.Bi/h5*1H3;^N Key: ARMZEJAYUBQCRQ-UHFFFAOYSA-N^N
SMILES C[Bi](C)(C)(C)C
Properties
Chemical formula	C₅H₁₅Bi
Molar mass	284.155 g·mol⁻¹
Appearance	blue-violet solid
Related compounds
Related compounds	Trimethylbismuth Pentamethylarsenic Pentamethylantimony Pentamethyltantalum Pentaphenylbismuth
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N (what is ^YN ?) Infobox references

Pentamethylbismuth (or pentamethylbismuthorane^[2]) is an organometalllic compound containing five methyl groups bound to a bismuth atom with formula Bi(CH₃)₅. It is an example of a hypervalent compound. The molecular shape is trigonal bipyramid.^[3]

Production

Pentamethylbismuth is produced in a two step process. First, trimethylbismuth is reacted with sulfuryl chloride to yield dichloro trimethylbismuth, which is then reacted with two equivalents of methyllithium dissolved in ether.^[4] The blue solution is cooled to −110 °C to precipitate the solid product.

Bi(CH₃)₃ + SO₂Cl₂ → Bi(CH₃)₃Cl₂ + SO₂

Bi(CH₃)₃Cl₂ + 2LiCH₃ → Bi(CH₃)₅ + 2LiCl

Properties

At -110 °C, Bi(CH₃)₅ is a blue-violet solid. The methyl groups are arranged in a trigonal bipyramid, and the bond-lengths of methyl with bismuth are all the same. However, the molecule is not rigid, as can be determined from the nuclear magnetic resonance spectrum that shows all methyl groups are equivalent.^[4] It is stable as a solid, but in the gas phase, when heated or in solution decomposes to trimethylbismuth.^[3]^[4] The colour is unusual for bismuth or other hypervalent pnictide compounds, which are colourless. Calculations show that the colour is due to HOMO-LUMO transition. The HOMO is ligand based, whereas the LUMO is modified by relativistically stabilised bismuth 6s orbitals.^[5]

Reactions

If excess methyllithium is used in production, an orange hexamethylbismuth salt, LiBi(CH₃)₆, is formed.^[6]^[4]

References

^ Urben, Peter (2013). Bretherick's Handbook of Reactive Chemical Hazards. Academic Press. p. 742. ISBN 9780080523408.
^ Hellwinkel, Dieter (1883). "Penta- and hexaorganyl derivatives of the main group five elements". Wittig Chemistry. Topics in Current Chemistry. Topics in Current Chemistry. 109: 1–63. doi:10.1007/BFb0018055. ISBN 3-540-11907-8.
^ ^a ^b Greene, Tim M.; Downs, Anthony J.; Pulham, Colin R.; Haaland, Arne; Verne, Hans Peter; Volden, Hans Vidar; Timofeeva, Tatjana V. (November 1998). "Molecular Structures of Pentamethylarsenic(V) and Trimethyldichloroarsenic(V) by Gas Electron Diffraction and ab Initio Calculations:? Molecular Mechanics Calculations on Pentamethylarsenic(V), Pentaphenylarsenic(V), and Related Compounds". Organometallics. 17 (24): 5287–5293. doi:10.1021/om980520r.
^ ^a ^b ^c ^d Wallenhauer, Stephan; Seppelt, Konrad (18 May 1994). "Methylbismuth(V) Compounds". Angewandte Chemie International Edition in English. 33 (9): 976–978. doi:10.1002/anie.199409761.
^ Conradie, Jeanet; Ghosh, Abhik (February 2017). "The Blue-Violet Color of Pentamethylbismuth: A Visible Spin-Orbit Effect". ChemistryOpen. 6 (1): 15–17. doi:10.1002/open.201600131. PMC 5288750. PMID 28168144.
^ Wallenhauer, Stephan; Seppelt, Konrad (January 1995). "Antimony(V) and Bismuth(V) Methyl Compounds: A Structural Comparison". Inorganic Chemistry. 34 (1): 116–119. doi:10.1021/ic00105a021.

Extra reading

Gagnon, Alexandre; Dansereau, Julien; Le Roch, Adrien (2 March 2017). "Organobismuth Reagents: Synthesis, Properties and Applications in Organic Synthesis". Synthesis. 49 (8): 1707–1745. doi:10.1055/s-0036-1589482. S2CID 102471505.

Bismuth compounds

Bismuth(III)

Organobismuth(III)	C₄H₄BiH

Bismuth(V)

Organobismuth(V)	Bi(CH₃)₅ Bi(C₆H₅)₅

Read other articles:

Hogere Burger School (Haarlem)

SchoolHoogere Burger SchoolLocationZijlvest 27 (corner Vestestraat-Oude Zijlvest), Haarlem, NetherlandsInformationTypePublic[1] Hogere burgerschool, Lyceum, and (for a few years) GymnasiumMottoOriginally occupying an entire city block, the building was built in 1906 to replace cramped quarters in the JacobijnestraatEstablished1864 The Hoogere Burger School is a former HBS Hogere burgerschool on the Zijlvest, Haarlem, The Netherlands. It was one of the oldest public schools in Haarlem,...

China Shipping Group

China Shipping beralih ke artikel ini: untuk anak usaha yang sebelumnya dikenal sebagai China Shipping Container Lines, lihat COSCO Shipping Development; untuk anak usaha yang sebelumnya dikenal sebagai China Shipping Development, lihat COSCO Shipping Energy. Untuk suksesor de facto, lihat China COSCO Shipping. Artikel ini bukan mengenai China Overseas Holdings, atau juga dikenal sebagai 中海集團/中海集团, atau Sino-Ocean Group. China Shipping Group Company, LimitedPeti kemas China Sh...

Basilika Rasul Santo Petrus, Los Chaguaramos

Basilika Rasul Santo PetrusBasilika Minor Rasul Santo PetrusSpanyol: Basílica San Pedro Apóstolcode: es is deprecated Basilika Rasul Santo PetrusLokasiCaracasNegara VenezuelaDenominasiGereja Katolik RomaArsitekturStatusBasilika minorStatus fungsionalAktifAdministrasiKeuskupan AgungKeuskupan Agung Caracas Basilika Rasul Santo Petrus (Spanyol: Basílica San Pedro Apóstolcode: es is deprecated ) adalah sebuah gereja basilika minor Katolik yang terletak di Los Chaguaramos, Venezuela. Basi...

Konferensi Berlin

Konferensi Berlin Konferensi Berlin, Konferensi Kongo (Jerman: Kongokonferenzcode: de is deprecated ), atau Konferensi Afrika Barat Berlin [1] (Jerman: Westafrika-Konferenzcode: de is deprecated ) tahun 1884–85 adalah konferensi yang mengatur penjajahan dan perdagangan Eropa di Afrika pada masa Imperialisme Baru yang bertepatan dengan bangkitnya Jerman sebagai kekuatan imperial. Konferensi ini diserukan oleh Kerajaan Portugal dan diorganisasikan oleh Otto von Bismarck, Kanselir Jerm...

Carlos Alvarado Quesada

President of Costa Rica from 2018 to 2022 This biography of a living person needs additional citations for verification. Please help by adding reliable sources. Contentious material about living persons that is unsourced or poorly sourced must be removed immediately from the article and its talk page, especially if potentially libelous.Find sources: Carlos Alvarado Quesada – news · newspapers · books · scholar · JSTOR (July 2017) (Learn how and when to...

Spandau

Lambang Peta Data dasar Bundesland: Berlin Luas wilayah: 91,91 km² Penduduk: 225 658 (akhir November 2004) Situs web resmi: BA Spandau Politik Wali kota: Helmut Kleebank (SPD) Pembagian kursi di DPRD (2011): SPD CDU GRÜNE PIRATEN LINKE 23 21 6 3 1 Spandau adalah sebuah Bezirk di Berlin, Jerman. Setelah Perang Dunia II pada tahun 1945 sehabisnya kekalahan Tentara Nazi Jerman, kawasan ini dimasukkan kepada sektor Britania di Berlin Barat. lbsDaftar Bezirke di BerlinBezirke di BerlinCharlotte...

Allegheny County belt system

Allegheny County belt system For the Pittsburgh Southern Beltway, see Pennsylvania Route 576. Allegheny County Belt System Static map of Allegheny County with the system Red Belt Orange Belt Yellow Belt Green Belt Blue Belt Purple Belt (River)System informationMaintained by ACDPW, PennDOT and city agenciesLength280.5 mi (451.4 km)Highway namesInterstatesInterstate nn (I-nn)US HighwaysU.S. R...

The Death Match

The Death MatchPoster resmi tentang pertandingan yang dicetak oleh pemerintah Jerman Start Flakelf 5 3 Tanggal9 Agustus 1942StadionZenit stadium[a], Kyiv, Reichskommissariat Ukraine← Start – Flakelf (6 Aug 1942) Start – Rukh (16 Aug 1942) → The Death Match (Ukraina: Матч смерті) (bahasa Rusia: Матч смерти) adalah nama yang diberikan dalam historiografi pascaperang untuk pertandingan sepak bola yang dimainkan di Kyiv di Reichskommissariat Ukr...

Синелобый амазон

Синелобый амазон Научная классификация Домен:ЭукариотыЦарство:ЖивотныеПодцарство:ЭуметазоиБез ранга:Двусторонне-симметричныеБез ранга:ВторичноротыеТип:ХордовыеПодтип:ПозвоночныеИнфратип:ЧелюстноротыеНадкласс:ЧетвероногиеКлада:АмниотыКлада:ЗавропсидыКласс:Пт�...

ロバート・デ・ニーロ

ロバート・デ・ニーロRobert De Niro 2011年のデ・ニーロ生年月日 (1943-08-17) 1943年8月17日（80歳）出生地アメリカ合衆国・ニューヨーク州ニューヨーク市身長 177 cm職業俳優、映画監督、映画プロデューサージャンル映画、テレビドラマ活動期間 1963年 -配偶者ダイアン・アボット（1976年 - 1988年）グレイス・ハイタワー（1997年 - ）主な作品『ミーン・ストリート』（1973年）...

Taman Peringatan Sandakan

Taman Peringatan SandakanHalaman utama taman tersebut.Koordinat5°53′19″N 118°2′50″E / 5.88861°N 118.04722°E / 5.88861; 118.04722Koordinat: 5°53′19″N 118°2′50″E / 5.88861°N 118.04722°E / 5.88861; 118.04722LokasiSandakanTipePrasastiDidedikasikan kepadaMengenang seluruh tahanan perang yang kehilangan nyawa mereka saat Pawai Kematian Sandakan Taman Peringatan Sandakan adalah sebuah situs peringatan yang dibangun di bekas hala...

大字 (数字)

この項目には、一部のコンピュータや閲覧ソフトで表示できない文字が含まれています（詳細）。数字の大字（だいじ）は、漢数字の一種。通常用いる単純な字形の漢数字（小字）の代わりに同じ音の別の漢字を用いるものである。概要壱万円日本銀行券（「壱」が大字）弐千円日本銀行券（「弐」が大字）漢数字には「一」「二」「三」と続く小字と、「壱」「�...

2016年美國總統選舉

2016年美國總統選舉 ← 2012 2016年11月8日 2020 → 538個選舉人團席位獲勝需270票民意調查投票率55.7%[1][2] ▲ 0.8 % 获提名人唐納·川普希拉莉·克林頓政党共和黨民主党家鄉州紐約州紐約州竞选搭档迈克·彭斯蒂姆·凱恩选举人票 304[3][4][註 1] 227[5] 胜出州/省 30 + 緬-2 20 + DC 民選得票 62,984,828[6] 65,853,514[6]...

Iglesia de San Ildefonso (Toledo)

Iglesia de San Ildefonso Bien de interés culturalPatrimonio histórico de España LocalizaciónPaís España EspañaComunidad Castilla-La Mancha Castilla-La ManchaLocalidad ToledoDatos generalesCategoría MonumentoCódigo RI-51-0008669Declaración 20-12-1994Construcción 1629 - 1765Estilo Barroco español[editar datos en Wikidata] Interior Cúpula y torres La iglesia de San Ildefonso es una iglesia de estilo barroco localizada en el centro del casco histórico de la ciuda...

It Was My Best Birthday Ever, Charlie Brown

1997 direct-to-video special directed by Bill Melendez It Was My Best Birthday Ever, Charlie BrownGenreAnimated telelvsion specialCreated byCharles M. SchulzWritten byCharles M. SchulzDirected byBill MelendezVoices ofSteven HartmanAnthony BurchJamie CroninDanielle KeatonBrandon TaylorBill MelendezMegan EllisTheme music composerVince GuaraldiOpening themeRollerbladingEnding themeRollerbladingComposersVince GuaraldiDavid BenoitCountry of originUnited StatesOriginal languageEnglishProductionExec...

Tatenokai

Nationalist private militia in Japan (1968–70) Tatenokai楯の會LeaderYukio MishimaDates of operation1968–1970Country JapanAllegiance Emperor of JapanIdeologyJapanese nationalismUltranationalism[1]TraditionalismAnti-communismMonarchismPolitical positionFar-rightSizeapprox. 90 The Tatenokai (楯の会, 楯の會) or Shield Society was a private militia in Japan dedicated to traditional Japanese values and veneration of the Emperor. It was founded and led by author Yukio ...

ليغا برو 2013–14

ليغا برو 2013–14 تفاصيل الموسم ليغا برو البلد البرتغال التاريخ بداية:11 أغسطس 2013 البطل موريرينسي مباريات ملعوبة 462 عدد المشاركين 22 أهداف مسجلة 1062 ليغا برو 2012–13 ليغا برو 2014–15 تعديل مصدري - تعديل ليغا برو 2013–14 (بالبرتغالية: Segunda Liga de 2013–14‏) �...

Love, Death & Robots

Adult animated anthology television series Love, Death & RobotsGenreAdult animationScience fantasyBlack comedyHorrorAnthologyCreated byTim MillerOriginal languageEnglishNo. of seasons3No. of episodes35ProductionExecutive producersDavid FincherTim MillerJennifer MillerJoshua DonenRunning time6–21 minutesProduction companiesBlur StudioNetflix StudiosOriginal releaseNetworkNetflixReleaseMarch 15, 2019 (2019-03-15) –present (present) Love, Death & Robots (stylized in al...

Edward C. Gleed

US Army Air Force officer with Buffalo Soldiers (1916–1990) Tuskegee Airman Edward Gleed with his P-51 Edward Creston Gleed (November 5, 1916 – January 25, 1990) was an U.S. Army Air Force officer with the famed Buffalo Soldiers/9th Cavalry Regiment (United States), 332nd Fighter Group’s operations officer, and combat fighter pilot with the 99th Fighter Squadron, best known as the Tuskegee Airmen.[1][2][3] He was one of the more prominent members of Tuskegee Airm...

Republic of Vietnam Navy

Former naval branch of the South Vietnamese military VNN redirects here. For other uses, see VNN (disambiguation). Republic of Vietnam NavyHải quân Việt Nam Cộng hòaEmblem of the South Vietnamese NavyFounded1952 (1952)Disbanded30 April 1975 (30 April 1975)Country South VietnamBranchNavyRoleSea controlSize42,000 men, 1,400 ships, boats and other vessels (1973)Part of Vietnamese National Army (1952-1955) Republic of Vietnam Military ForcesGarrison/HQSaigon, South Vie...