カリセン

カリセン
IUPAC名

5-(2-Cyclopropen-1-ylidene)-1,3-cyclopentadiene

別称
Triapentafulvalene
識別情報
CAS登録番号 6249-23-6
PubChem 12302244
ChemSpider 26537418
特性
化学式 C8H6
モル質量 102.13 g mol−1
特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

カリセン(Calicene)またはトリアペンタフルバレン(Triapentafulvalene)は、化学式C8H6のフルバレン系炭化水素である。シクロペンタジエン環とシクロプロペン環が結合した構造を持つ。

性質

共鳴効果により2つの環の電荷が異なっており、高い極性を持つ。

ヒュッケル則によると、非常に高い共鳴エネルギーを持つと予測されるが[1]、実際には高くはない。各々2π電子系、6π電子系のヒュッケル則安定性を保ったまま三員環の炭素原子上に部分正電荷、五員環の炭素原子上に部分負電荷を置き、中央の二重結合は分極しており、双極子モーメントは4.66 Dと計算される[2]。trans-ビカリセン[2]（環状化合物）やポリ-2,7-[N]カリセン[3]（鎖状化合物）等の2つ以上のカリセンサブユニットを含むいくつかの化合物には、芳香族性がある。

作成の試みが行われているが、カリセンそのものの合成には、これまで成功していない[4]。しかし、1,2,3,4,5,6-ヘキサフェニルカリセンは合成され、双極子モーメントは6.3 Dと測定されている[5]。

出典

  1. ^ Schaad, L. J.; B. Andes Hess , Jr (2001). “Dewar Resonance Energy”. Chemical Reviews 101 (5): 1465-1476. doi:10.1021/cr9903609. 
  2. ^ a b Oziminski, W. P.; M. Palusia (2013). “Capturing the elusive aromaticity of bicalicene”. Physical Chemistry Chemical Physics 15 (9): 3286-3293. Bibcode: 2013PCCP...15.3286O. doi:10.1039/C2CP43426A. PMID 23358331. 
  3. ^ Ratanadachanakin, Thawalrat; Collier, Willard E. r (2015). “Aromaticity of a series of poly-2,7-[Ncalicenes”]. Maejo International Journal of Science and Technology 9 (1): 21-31. http://www.mijst.mju.ac.th/vol9/21-31.pdf. 
  4. ^ de Meijere, Armin (2014). Houben-Weyl Methods of Organic Chemistry Vol. E 17d, 4th Edition Supplement: Carbocyclic Three-Membered Ring Compounds, Cyclopropenes, Author Index, Compound Index. Stuttgart: Georg Thieme Verlag. pp. 2967. ISBN 978-3131819741 
  5. ^ Agranat, Israel; Bergmann, Ernst D. (1965-01-01). “Hexaphenyltriapentafulvalene” (英語). Chemical Communications (London) 0 (21): 512-513. doi:10.1039/C19650000512. ISSN 0009-241X. 

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