zh 环［18］碳

环［18］碳
识别
CAS号	126487-09-0
PubChem	14940714
ChemSpider	74015635
SMILES	C1#CC#CC#CC#CC#CC#CC#CC#CC#C1;
性质
化学式	C18
摩尔质量	216.19 g·mol⁻¹
密度	1.38±0.1 g·cm−3（20 °C）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

环[18]碳或环十八-1,3,5,7,9,11,13,15,17-九炔是碳的同素異形體之一，化学式为C
18，几乎不溶于水。^[1]它是一种环碳和多炔，由十八个碳原子以单叁键交替构成环。环[18]碳是预测能够热力学稳定最小的环[n]碳，理论应变能为72 kcal/mol。^[2]^[3]

历史和制备

早在1991年，便有人对环[18]碳的结构进行预测，并进行过有关计算，^[4]但其合成却在2019年才被IBM和牛津大学的联合团队^[5]通过环丁酮结构的数个位点进行电化学脱羰基反应制得：^[6]

它也可由C₁₈Br₆的脱溴反应制得。^[7]

性质

IBM研究人员发现，环[18]碳的电子结构（英语：electronic structure）由交替的单叁键构成，而非累计双键结构，它在理论上是一种半导体。^[6]

在该化合物中，C—C键的键长为1.36 Å，C≡C的键长为1.20 Å。^[5]

参考文献

^ ^1.0 ^1.1 Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2019 ACD/Labs). Retrieved from SciFinder. [2019-8-21]
^ George A. Adamson; Charles W. Rees. Towards the total synthesis of cyclo[n]carbons and the generation of cyclo[6]carbon. J. Chem. Soc., Perkin Trans. 1. 1996, (13): 1535–1543. doi:10.1039/P19960001535.
^ François Diederich; Yves Rubin; Carolyn B. Knobler; Robert L. Whetten; Kenneth E. Schriver; Kendall N. Houk; Yi Li. All-Carbon Molecules: Evidence for the Generation of Cyclo[18]carbon from a Stable Organic Precursor. Science. 1989-09-08, 245 (4922): 1088–1090. Bibcode:1989Sci...245.1088D. PMID 17838807. doi:10.1126/science.245.4922.1088.
^ Parasuk, Vudhichai; Almlof, Jan; Feyereisen, Martin W. The [18] all-carbon molecule: cumulene or polyacetylene?. Journal of the American Chemical Society. 1991, 113 (3): 1049–1050. ISSN 0002-7863. doi:10.1021/ja00003a052.
^ ^5.0 ^5.1 Kaiser, Katharina; Scriven, Lorel M.; Schulz, Fabian; Gawel, Przemyslaw; Gross, Leo; Anderson, Harry L. An sp-hybridized molecular carbon allotrope, cyclo[18]carbon. Science. 2019-08-15 [2019-08-21]. doi:10.1126/science.aay1914. （原始内容存档于2019-08-21）.
^ ^6.0 ^6.1 Castelvecchi, Davide. Chemists make first-ever ring of pure carbon. Nature. 2019-08-15 [2019-08-16]. doi:10.1038/d41586-019-02473-z. （原始内容存档于2019-08-16）（英语）.
^ Lorel M. Scriven, Katharina Kaiser, Fabian Schulz, Alistair J. Sterling, Steffen L. Woltering, Przemyslaw Gawel, Kirsten E. Christensen, Harry L. Anderson, Leo Gross. Synthesis of Cyclo[18]carbon via Debromination of C 18 Br 6. Journal of the American Chemical Society. 2020-07-29, 142 (30): 12921–12924 [2020-08-22]. ISSN 0002-7863. doi:10.1021/jacs.0c05033. （原始内容存档于2020-10-17）（英语）.

拓展阅读

Sen, Sabyasachi; Seal, Prasenjit; Chakrabarti, Swapan. Explicit role of dynamical and nondynamical electron correlations on broken symmetry inC_4N+2clusters. Physical Review B. 2006, 73 (24). ISSN 1098-0121. doi:10.1103/PhysRevB.73.245401.
Feyereisen, Martin; Gutowski, Maciej; Simons, Jack; Almlöf, Jan. Relative stabilities of fullerene, cumulene, and polyacetylene structures for C_n:n=18–60. The Journal of Chemical Physics. 1992, 96 (4): 2926–2932. ISSN 0021-9606. doi:10.1063/1.461989.
Murphy, Veronica L.; Farfan, Camille; Kahr, Bart. Chiroptical structure-property relations in cyclo[18]carbon and its in silico hydrogenation products. Chirality. 2018, 30 (4): 325–331. ISSN 0899-0042. doi:10.1002/chir.22817.

[sci-1] 1.0 ^1.1 Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2019 ACD/Labs). Retrieved from SciFinder. [2019-8-21]

[adaree-2] George A. Adamson; Charles W. Rees. Towards the total synthesis of cyclo[n]carbons and the generation of cyclo[6]carbon. J. Chem. Soc., Perkin Trans. 1. 1996, (13): 1535–1543. doi:10.1039/P19960001535.

[diederich89-3] François Diederich; Yves Rubin; Carolyn B. Knobler; Robert L. Whetten; Kenneth E. Schriver; Kendall N. Houk; Yi Li. All-Carbon Molecules: Evidence for the Generation of Cyclo[18]carbon from a Stable Organic Precursor. Science. 1989-09-08, 245 (4922): 1088–1090. Bibcode:1989Sci...245.1088D. PMID 17838807. doi:10.1126/science.245.4922.1088.

[4] Parasuk, Vudhichai; Almlof, Jan; Feyereisen, Martin W. The [18] all-carbon molecule: cumulene or polyacetylene?. Journal of the American Chemical Society. 1991, 113 (3): 1049–1050. ISSN 0002-7863. doi:10.1021/ja00003a052.

[Kaiser-5] 5.0 ^5.1 Kaiser, Katharina; Scriven, Lorel M.; Schulz, Fabian; Gawel, Przemyslaw; Gross, Leo; Anderson, Harry L. An sp-hybridized molecular carbon allotrope, cyclo[18]carbon. Science. 2019-08-15 [2019-08-21]. doi:10.1126/science.aay1914. （原始内容存档于2019-08-21）.

[Castelvecchi-6] 6.0 ^6.1 Castelvecchi, Davide. Chemists make first-ever ring of pure carbon. Nature. 2019-08-15 [2019-08-16]. doi:10.1038/d41586-019-02473-z. （原始内容存档于2019-08-16）（英语）.

[7] Lorel M. Scriven, Katharina Kaiser, Fabian Schulz, Alistair J. Sterling, Steffen L. Woltering, Przemyslaw Gawel, Kirsten E. Christensen, Harry L. Anderson, Leo Gross. Synthesis of Cyclo[18]carbon via Debromination of C 18 Br 6. Journal of the American Chemical Society. 2020-07-29, 142 (30): 12921–12924 [2020-08-22]. ISSN 0002-7863. doi:10.1021/jacs.0c05033. （原始内容存档于2020-10-17）（英语）.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

Agama	Bahasa	Biografi	Budaya	Ekonomi	Elektronika
Film	Filsafat	Geografi	Indonesia	Ilmu	Lingkungan
Masyarakat	Matematika	Militer	Mitologi	Musik	Olahraga
Pendidikan	Politik	Sastra	Sejarah	Seni	Teknologi

环［18］碳

历史和制备

性质

参考文献

拓展阅读

Portal di Ensiklopedia Dunia