二苯基锡

二苯基锡
识别
CAS号	6381-06-2
PubChem	70535
SMILES	c1ccccc1[Sn]c2ccccc2;
性质
化学式	C12H10Sn
摩尔质量	272.92 g·mol−1
相关物质
相关化学品	四苯基锡; 二苯基锡烷
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

二苯基锡是化学式 (C₆H₅)₂Sn的有机锡化合物，目前仍未被分离。

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历史

早在1920年，Erich Krause和Reinhard Becker就尝试通过苯基溴化镁和无水氯化亚锡反应得到二苯基锡。^[1]反应得到了黄色固体，但在1963年Wilhelm P. Neumann和Klaus König发现这种黄色固体其实是二苯基锡的聚合物。^[2]

1926年，Robert F. Chambers和Philip C. Scherer试图通过二苯基二氯化锡和钠反应得到二苯基锡^[3]，但Neumann和König在1963年发现真正的反应产物是二苯基锡烷。^[2]

制备和反应

二苯基锡可以由二苯基二氯化锡和萘钠反应而成，但产物不能分离，会立刻反应生成六聚体：^[2]

二苯基锡也可以由3,4-二取代-1,1-二苯基锡代环-3-戊烯的热分解^[4]或光解^[5]而成。反应产生的二苯基锡在合适的试剂存在下可以被截获，^[5]但如果没有截获试剂则也会形成聚合物。^[6]

和大多数锡烯一样，计算化学显示二苯基锡的二聚体四苯基乙锡烯比单体稳定47.7 kJ/mol。四苯基乙锡烯还能变成二苯基锡的二苯基锡配合物，能量降低20.5 kJ/mol。不过，Sn₂Ph₄最稳定的结构是PhSnSnPh₃。在二苯基锡的二聚反应中，这些过渡态会依序出现。^[5]

二苯基锡可以作为簇合物中的配体。^[7]^[8]

结构

根据计算，二苯基锡的C–Sn–C键角为97.4°，Sn–C键长为2.18 Å。^[5]

参考资料

[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.
[2]
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 （德语）.
[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.
[4]
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]
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.
[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.

[1] [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]
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 （德语）.

[:0-3] [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]
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]
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] [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] [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] [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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