二苯基錫

二苯基錫
識別
CAS號	6381-06-2
PubChem	70535
SMILES	c1ccccc1[Sn]c2ccccc2;
性質
化學式	C12H10Sn
摩爾質量	272.92 g·mol−1
相關物質
相關化學品	四苯基錫; 二苯基錫烷
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

二苯基錫是化學式 (C₆H₅)₂Sn的有機錫化合物，目前仍未被分離。

歷史

早在1920年，Erich Krause和Reinhard Becker就嘗試通過苯基溴化鎂和無水氯化亞錫反應得到二苯基錫。^[1]反應得到了黃色固體，但在1963年Wilhelm P. Neumann和Klaus König發現這種黃色固體其實是二苯基錫的聚合物。^[2]

1926年，Robert F. Chambers和Philip C. Scherer試圖通過二苯基二氯化錫和鈉反應得到二苯基錫^[3]，但Neumann和König在1963年發現真正的反應產物是二苯基錫烷。^[2]

製備和反應

二苯基錫可以由二苯基二氯化錫和萘鈉反應而成，但產物不能分離，會立刻反應生成六聚體：^[2]

二苯基錫也可以由3,4-二取代-1,1-二苯基錫代環-3-戊烯的熱分解^[4]或光解^[5]而成。反應產生的二苯基錫在合適的試劑存在下可以被截獲，^[5]但如果沒有截獲試劑則也會形成聚合物。^[6]

和大多數錫烯一樣，計算化學顯示二苯基錫的二聚體四苯基乙錫烯比單體穩定47.7 kJ/mol。四苯基乙錫烯還能變成二苯基錫的二苯基錫配合物，能量降低20.5 kJ/mol。不過，Sn₂Ph₄最穩定的結構是PhSnSnPh₃。在二苯基錫的二聚反應中，這些過渡態會依序出現。^[5]

二苯基錫可以作為簇合物中的配體。^[7]^[8]

結構

根據計算，二苯基錫的C–Sn–C鍵角為97.4°，Sn–C鍵長為2.18 Å。^[5]

參考資料

^ Krause, Erich; Becker, Reinhard. Zweiwertiges Zinn als Chromophor in aromatischen Stannoverbindungen und die Gewinnung von Hexaaryl‐distannanen. Berichte der deutschen chemischen Gesellschaft (A and B Series) (Wiley). 1920-02-14, 53 (2): 173–190. ISSN 0365-9488. doi:10.1002/cber.19200530209.
^ ^2.0 ^2.1 ^2.2 ^2.3 ^2.4 ^2.5 Neumann, Wilhelm P.; König, Klaus. Organozinnverbindungen, VII. Über Diphenylzinn. Justus Liebigs Annalen der Chemie (Wiley). 1964-10-07, 677 (1): 1–11. ISSN 0075-4617. doi:10.1002/jlac.19646770102 （德語）.
^ Chambers, Robert F.; Scherer, Philip C. PHENYLTIN COMPOUNDS. Journal of the American Chemical Society (American Chemical Society (ACS)). 1926, 48 (4): 1054–1062. ISSN 0002-7863. doi:10.1021/ja01415a026.
^ ^4.0 ^4.1 Zhou, Dong; Reiche, Clemens; Nag, Mrinmoy; Soderquist, John A.; Gaspar, Peter P. Synthesis of 1-Stannacyclopent-3-enes and Their Pyrolysis to Stannylenes. Organometallics (American Chemical Society (ACS)). 2009-03-31, 28 (8): 2595–2608. ISSN 0276-7333. doi:10.1021/om800541f.
^ ^5.0 ^5.1 ^5.2 ^5.3 ^5.4 ^5.5 Duffy, Ian R.; Leigh, William J. Direct Detection, Dimerization, and Chemical Trapping of Dimethyl- and Diphenylstannylene from Photolysis of Stannacyclopent-3-enes in Solution. Organometallics (American Chemical Society (ACS)). 2015-09-22, 34 (20): 5029–5044. ISSN 0276-7333. doi:10.1021/acs.organomet.5b00615.
^ Duffy, Ian R.; Leigh, William J. Fast kinetics studies of the Lewis acid–base complexation of transient stannylenes with σ- and π-donors in solution. Physical Chemistry Chemical Physics (Royal Society of Chemistry (RSC)). 2018, 20 (31): 20555–20570. ISSN 1463-9076. doi:10.1039/c8cp03580f.
^ Adams, Richard D.; Captain, Burjor; Zhu, Lei. A New Tris(diphenylstannylene)triosmium Carbonyl Cluster Complex and Its Reactions with Pt(PBut3)2 and Pt(PPh3)4. Organometallics (American Chemical Society (ACS)). 2006-03-09, 25 (8): 2049–2054. ISSN 0276-7333. doi:10.1021/om060002d.
^ Baumgartner, Judith; Marschner, Christoph. Coordination of non-stabilized germylenes, stannylenes, and plumbylenes to transition metals. Reviews in Inorganic Chemistry (Walter de Gruyter GmbH). 2014-06-01, 34 (2): 119–152. ISSN 2191-0227. doi:10.1515/revic-2013-0014.

[1] Krause, Erich; Becker, Reinhard. Zweiwertiges Zinn als Chromophor in aromatischen Stannoverbindungen und die Gewinnung von Hexaaryl‐distannanen. Berichte der deutschen chemischen Gesellschaft (A and B Series) (Wiley). 1920-02-14, 53 (2): 173–190. ISSN 0365-9488. doi:10.1002/cber.19200530209.

[Neumann-2] 2.0 ^2.1 ^2.2 ^2.3 ^2.4 ^2.5 Neumann, Wilhelm P.; König, Klaus. Organozinnverbindungen, VII. Über Diphenylzinn. Justus Liebigs Annalen der Chemie (Wiley). 1964-10-07, 677 (1): 1–11. ISSN 0075-4617. doi:10.1002/jlac.19646770102 （德語）.

[:0-3] Chambers, Robert F.; Scherer, Philip C. PHENYLTIN COMPOUNDS. Journal of the American Chemical Society (American Chemical Society (ACS)). 1926, 48 (4): 1054–1062. ISSN 0002-7863. doi:10.1021/ja01415a026.

[Gaspar-4] 4.0 ^4.1 Zhou, Dong; Reiche, Clemens; Nag, Mrinmoy; Soderquist, John A.; Gaspar, Peter P. Synthesis of 1-Stannacyclopent-3-enes and Their Pyrolysis to Stannylenes. Organometallics (American Chemical Society (ACS)). 2009-03-31, 28 (8): 2595–2608. ISSN 0276-7333. doi:10.1021/om800541f.

[Leigh-5] 5.0 ^5.1 ^5.2 ^5.3 ^5.4 ^5.5 Duffy, Ian R.; Leigh, William J. Direct Detection, Dimerization, and Chemical Trapping of Dimethyl- and Diphenylstannylene from Photolysis of Stannacyclopent-3-enes in Solution. Organometallics (American Chemical Society (ACS)). 2015-09-22, 34 (20): 5029–5044. ISSN 0276-7333. doi:10.1021/acs.organomet.5b00615.

[Leigh2-6] Duffy, Ian R.; Leigh, William J. Fast kinetics studies of the Lewis acid–base complexation of transient stannylenes with σ- and π-donors in solution. Physical Chemistry Chemical Physics (Royal Society of Chemistry (RSC)). 2018, 20 (31): 20555–20570. ISSN 1463-9076. doi:10.1039/c8cp03580f.

[7] Adams, Richard D.; Captain, Burjor; Zhu, Lei. A New Tris(diphenylstannylene)triosmium Carbonyl Cluster Complex and Its Reactions with Pt(PBut3)2 and Pt(PPh3)4. Organometallics (American Chemical Society (ACS)). 2006-03-09, 25 (8): 2049–2054. ISSN 0276-7333. doi:10.1021/om060002d.

[8] Baumgartner, Judith; Marschner, Christoph. Coordination of non-stabilized germylenes, stannylenes, and plumbylenes to transition metals. Reviews in Inorganic Chemistry (Walter de Gruyter GmbH). 2014-06-01, 34 (2): 119–152. ISSN 2191-0227. doi:10.1515/revic-2013-0014.

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