磷雜苯

磷雜苯
Kekulé skeletal formula of phosphorine	Aromatic ball and stick model of phosphorine
	IUPAC名; Phosphinine
別名	Phosphabenzene
識別
CAS號	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
性質
化學式	C5H5P
摩爾質量	96.07 g·mol−1
相關物質
相關化學品	吡啶; 砷雜苯; 銻雜苯; 鉍雜苯
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

磷雜苯是一種有機化合物，化學式為C₅H₅P，它是吡啶的類似物。它是對空氣敏感的油狀液體，^[2]在惰性氣氛中穩定。^[3]^[4]相比之下，矽雜苯不僅對氧和潮濕敏感，在沒有大位阻的取代基的存在下，對熱也不穩定。

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1966年，Gottfried Märkl通過吡喃鎓鹽和膦試劑（如P(CH₂OH)₃或P(SiMe₃)₃）的縮合反應製得了第一個磷雜苯（2,4,6-三苯基磷雜苯）。^[3]

1971年，不含取代基的磷雜苯由Arthur J. Ashe III製得。^[2]^[5]

電子繞射表明，磷雜苯的芳香性為苯的88%，P-C鍵長為173 pm，C-C鍵長為140 pm左右。^[6]

儘管磷雜苯和吡啶結構上具有相似性，但磷雜苯的鹼性很弱，C₅H₅PH⁺和C₅H₅NH⁺的pK_a分別為-16.1和5.2。^[7]甲基鋰與磷雜苯作用在磷原子上，而與吡啶作用在鄰位上。^[8]

磷雜苯可以作為配體，形成普通的配合物或π-配合物，如V(η⁶-C₅H₅P)₂。^[7]聯(磷雜苯)（聯吡啶的類似物）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) （頁面存檔備份，存於互聯網檔案館）
[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  （英語）.
[5]
Greenwood, Norman Neill; Earnshaw, Alan. Chemistry of the elements. 2016: 544. ISBN 978-0-7506-3365-9. OCLC 1040112384 （英語）.
[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.

六磷雜苯（英語：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) （頁面存檔備份，存於互聯網檔案館）

[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  （英語）.

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

[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

[2]

[3]

[4]

[1]

[5]

[6]

[7]

[8]

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磷雜苯

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歷史

結構及性質

參考文獻

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