Cyclooctadecanonaene

Cyclooctadecanonaene
"Herringbone" crystal structure of [18]annulene
Names
Preferred IUPAC name
(1Z,3E,5E,7Z,9E,11E,13Z,15E,17E)-Cyclooctadeca-1,3,5,7,9,11,13,15,17-nonaene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C18H18/c1-2-4-6-8-10-12-14-16-18-17-15-13-11-9-7-5-3-1/h1-18H/b2-1-,3-1+,4-2+,5-3+,6-4+,7-5-,8-6-,9-7+,10-8+,11-9+,12-10+,13-11-,14-12-,15-13+,16-14+,17-15+,18-16+,18-17- ☒N
    Key: STQWAGYDANTDNA-DWSNDWDZSA-N ☒N
  • InChI=1/C18H18/c1-2-4-6-8-10-12-14-16-18-17-15-13-11-9-7-5-3-1/h1-18H/b2-1-,3-1+,4-2+,5-3+,6-4+,7-5-,8-6-,9-7+,10-8+,11-9+,12-10+,13-11-,14-12-,15-13+,16-14+,17-15+,18-16+,18-17-
    Key: STQWAGYDANTDNA-DWSNDWDZBB
  • C1=CC=CC=CC=CC=CC=CC=CC=CC=C1
Properties
C18H18
Molar mass 234.3 g·mol−1
Appearance red-brown crystals
Density 1.134 g/cm3 (calc.)[1]
Structure[1]
monoclinic, P21/a
a = 1.4984 (5) nm, b = 0.4802(2) nm, c = 1.0260(3) nm
α = 90°, β = 111.52(1)°, γ = 90°
2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclooctadecanonaene or [18]annulene is an organic compound with chemical formula C
18
H
18
. It belongs to the class of highly conjugated compounds known as annulenes and is aromatic. The usual isomer that [18]annulene refers to is the most stable one, containing six interior hydrogens and twelve exterior ones, with the nine formal double bonds in the cis,trans,trans,cis,trans,trans,cis,trans,trans configuration. It is reported to be a red-brown crystalline solid.

  1. ^ a b Gorter, S.; Rutten-Keulemans, E.; Krever, M.; Romers, C.; Cruickshank, D. W. J. (1995). "[18]-Annulene, C18H18, structure, disorder and Hückel's 4 n + 2 rule". Acta Crystallographica Section B Structural Science. 51 (6): 1036–1045. Bibcode:1995AcCrB..51.1036G. doi:10.1107/S0108768195004927.

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