磷杂苯

磷杂苯
Kekulé skeletal formula of phosphorine	Aromatic ball and stick model of phosphorine
	IUPAC名; Phosphinine
别名	Phosphabenzene
识别
CAS号	289-68-9
PubChem	123046
ChemSpider	109668
SMILES	C1=CC=PC=C1;
InChI	1/C5H5P/c1-2-4-6-5-3-1/h1-5H;
InChIKey	UNQNIRQQBJCMQR-UHFFFAOYAZ
MeSH	Phosphinine
性质
化学式	C5H5P
摩尔质量	96.07 g·mol−1
相关物质
相关化学品	吡啶; 砷杂苯; 锑杂苯; 铋杂苯
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

磷杂苯是一种有机化合物，化学式为C₅H₅P，它是吡啶的类似物。它是对空气敏感的油状液体，^[2]在惰性气氛中稳定。^[3]^[4]相比之下，硅杂苯不仅对氧和潮湿敏感，在没有大位阻的取代基的存在下，对热也不稳定。

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1966年，Gottfried Märkl通过吡喃𬭩盐和膦试剂（如P(CH₂OH)₃或P(SiMe₃)₃）的缩合反应制得了第一个磷杂苯（2,4,6-三苯基磷杂苯）。^[3]

1971年，不含取代基的磷杂苯由Arthur J. Ashe III制得。^[2]^[5]

电子衍射表明，磷杂苯的芳香性为苯的88%，P-C键长为173 pm，C-C键长为140 pm左右。^[6]

尽管磷杂苯和吡啶结构上具有相似性，但磷杂苯的碱性很弱，C₅H₅PH⁺和C₅H₅NH⁺的pK_a分别为-16.1和5.2。^[7]甲基锂与磷杂苯作用在磷原子上，而与吡啶作用在邻位上。^[8]

磷杂苯可以作为配体，形成普通的配合物或π-配合物，如V(η⁶-C₅H₅P)₂。^[7]联(磷杂苯)（联吡啶的类似物）的配合物也是已知的。

[1]
CHAPTER P-1. General Principles, Rules, and Conventions. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014: 47. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-00001.
[2]
Ashe, A. J. Phosphabenzene and Arsabenzene. Journal of the American Chemical Society. 1971, 93 (13): 3293–3295. doi:10.1021/ja00742a038.
[3]
G. Märkl, 2,4,6-Triphenylphosphabenzol in Angewandte Chemie 78, 907–908 (1966) （页面存档备份，存于互联网档案馆）
[4]
Newland, R. J.; Wyatt, M. F.; Wingad, R. L.; Mansell, S. M. A ruthenium( ii ) bis(phosphinophosphinine) complex as a precatalyst for transfer-hydrogenation and hydrogen-borrowing reactions. Dalton Transactions. 2017, 46 (19): 6172–6176. ISSN 1477-9226. PMID 28436519. doi:10.1039/C7DT01022B  （英语）.
[5]
Greenwood, Norman Neill; Earnshaw, Alan. Chemistry of the elements. 2016: 544. ISBN 978-0-7506-3365-9. OCLC 1040112384 （英语）.
[6]
László Nyulászi "Aromaticity of Phosphorus Heterocycles" Chem. Rev., 2001, volume 101, pp 1229–1246. doi:10.1021/cr990321x
[7]
François Mathey "Phosphorus Heterocycles" in Modern Heterocyclic Chemistry, First Edition, edited by Julio Alvarez-Builla, Juan Jose Vaquero, José Barluenga, Wiley-VCH, Weinheim, 2011. doi:10.1002/9783527637737.ch23.
[8]
Ashe III, Arthur J.; Smith, Timothy W. "The reaction of phosphabenzene, arsabenzene and stibabenzene with methyllithium." Tetrahedron Letters 1977, volume 18, pp. 407-410. doi:10.1016/S0040-4039(01)92651-6

Quin, L. D. A Guide to Organophosphorus Chemistry. Wiley-Interscience. 2000. ISBN 978-0-471-31824-8.

六磷杂苯（英语：Hexaphosphabenzene）

[iupac2013-1] [1]
CHAPTER P-1. General Principles, Rules, and Conventions. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014: 47. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-00001.

[Ashe-2] [2]
Ashe, A. J. Phosphabenzene and Arsabenzene. Journal of the American Chemical Society. 1971, 93 (13): 3293–3295. doi:10.1021/ja00742a038.

[:0-3] [3]
G. Märkl, 2,4,6-Triphenylphosphabenzol in Angewandte Chemie 78, 907–908 (1966) （页面存档备份，存于互联网档案馆）

[4] [4]
Newland, R. J.; Wyatt, M. F.; Wingad, R. L.; Mansell, S. M. A ruthenium( ii ) bis(phosphinophosphinine) complex as a precatalyst for transfer-hydrogenation and hydrogen-borrowing reactions. Dalton Transactions. 2017, 46 (19): 6172–6176. ISSN 1477-9226. PMID 28436519. doi:10.1039/C7DT01022B  （英语）.

[5] [5]
Greenwood, Norman Neill; Earnshaw, Alan. Chemistry of the elements. 2016: 544. ISBN 978-0-7506-3365-9. OCLC 1040112384 （英语）.

[6] [6]
László Nyulászi "Aromaticity of Phosphorus Heterocycles" Chem. Rev., 2001, volume 101, pp 1229–1246. doi:10.1021/cr990321x

[Mathey-7] [7]
François Mathey "Phosphorus Heterocycles" in Modern Heterocyclic Chemistry, First Edition, edited by Julio Alvarez-Builla, Juan Jose Vaquero, José Barluenga, Wiley-VCH, Weinheim, 2011. doi:10.1002/9783527637737.ch23.

[8] [8]
Ashe III, Arthur J.; Smith, Timothy W. "The reaction of phosphabenzene, arsabenzene and stibabenzene with methyllithium." Tetrahedron Letters 1977, volume 18, pp. 407-410. doi:10.1016/S0040-4039(01)92651-6

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磷杂苯

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结构及性质

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