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Despite several attempts to prepare it, the parent calicene has so far defied attempts at synthesis. However, 1,2,3,4,5,6-hexaphenylcalicene has been prepared and an experimental dipole moment of 6.3 D was measured.
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Methods of Organic Chemistry Vol. E 17d, 4th Edition Supplement: Carbocyclic Three-Membered Ring Compounds, Cyclopropenes, Author Index, Compound Index
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with a partial positive charge on the carbon atom of triangular ring and a partial negative charge on the carbon atom of pentagonal ring, in keeping with added
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and 6 π electrons respectively. Calicene's dipole moment has been computed to be 4.66
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Oziminski, W. P.; M. Palusia (2013). "Capturing the elusive aromaticity of bicalicene".
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366:. Several compounds that contains two or more calicene subunits are aromatic, such as
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Agranat, Israel; Bergmann, Ernst D. (1965-01-01). "Hexaphenyltriapentafulvalene".
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Except where otherwise noted, data are given for materials in their
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Schaad, L. J.; B. Andes Hess, Jr (2001). "Dewar
Resonance Energy".
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Ratanadachanakin, Thawalrat; Collier, Willard E. R. (2015).
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477:"Aromaticity of a series of poly-2,7-[N]calicenes"
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373:(ring compound) or poly-2,7-calicenes (chain compound)
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505:. Stuttgart: Georg Thieme Verlag. p. 2967.
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44:5-(Cycloprop-2-en-1-ylidene)cyclopenta-1,3-diene
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346:Very high resonance energy is predicted by the
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201:InChI=1S/C8H6/c1-2-4-7(3-1)8-5-6-8/h1-6H
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358:stability of rings containing 2
334:. Its name is derived from the Latin
204:Key: ZXWMPJFQZJXFQN-UHFFFAOYSA-N
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624:Polycyclic nonaromatic hydrocarbons
434:Physical Chemistry Chemical Physics
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338:meaning "goblet", from its shape.
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639:Hypothetical chemical compounds
280:(at 25 °C , 100 kPa).
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577:. You can help Knowledge by
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501:de Meijere, Armin (2014).
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528:Chemical Communications
569:This article about a
536:10.1039/C19650000512
40:Preferred IUPAC name
446:2013PCCP...15.3286O
270: g·mol
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454:10.1039/C2CP43426A
300:triapentafulvalene
284:Infobox references
225:C1(C=CC=C1)=C2C=C2
53:Triapentafulvalene
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644:Hydrocarbon stubs
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408:10.1021/cr9903609
330:ring linked by a
292:Chemical compound
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157:CompTox Dashboard
100:Interactive image
16:Chemical compound
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440:(9): 3286–3293.
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241:Chemical formula
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324:cyclopentadiene
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59:Identifiers
51:Other names
571:hydrocarbon
490:(1): 21–31.
371:-bicalicene
360:π electrons
332:double bond
326:ring and a
304:hydrocarbon
234:Properties
629:Fulvalenes
618:Categories
381:References
342:Properties
263:Molar mass
111:ChemSpider
87:3D model (
66:CAS Number
544:0009-241X
352:polarized
76:6249-23-6
20:Calicene
462:23358331
416:11710229
296:Calicene
145:12302244
120:26537418
442:Bibcode
306:of the
268:102.136
132:PubChem
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218:SMILES
34:Names
573:is a
480:(PDF)
369:trans
336:calix
310:with
302:is a
193:InChI
89:JSmol
575:stub
540:ISSN
507:ISBN
458:PMID
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532:doi
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298:or
162:EPA
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364:D
320:6
318:H
316:8
314:C
256:6
253:H
250:8
247:C
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160:(
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