Cyclo(18)carbon

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Cyclo[18]carbon
Polyynic cyclocarbon.png
Names
Preferred IUPAC name
Cyclooctadeca-1,3,5,7,9,11,13,15,17-nonayne
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C18/c1-2-4-6-8-10-12-14-16-18-17-15-13-11-9-7-5-3-1
    Key: GPWDPLKISXZVIE-UHFFFAOYSA-N
  • C1#CC#CC#CC#CC#CC#CC#CC#CC#C1
Properties
C18
Molar mass 216.198 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyclooctadeca-1,3,5,7,9,11,13,15,17-nonayne or cyclo[18]carbon is an allotrope of carbon with molecular formula C
18
. The molecule is a ring of eighteen carbon atoms, connected by alternating triple and single bonds; thus, it is a polyyne and a cyclocarbon.

Cyclo[18]carbon is the smallest cyclo[n]carbon predicted to be thermodynamically stable, with a computed strain energy of 72 kilocalories per mole. [1] Above 122 K, it explosively decomposes to amorphous graphite. [2]

A collaboration of teams at IBM and the University of Oxford team claimed to synthesize it in solid state in 2019 [3] by electrochemical decarbonylation of several sites of a cyclobutanone structure: [4] Later, researchers from Spain have used computational techniques to probe the structural and electronic properties of the molecule, and have discovered it to be an electron acceptor. [5]

Synthesis of cyclocarbon Synthese C18.svg
Synthesis of cyclocarbon

According to these IBM researchers, the electronic structure of their product consists of alternating triple bonds and single bonds, rather than a cumulene-type structure of consecutive double bonds. This supposedly makes this molecule a semiconductor. [4]

Related Research Articles

<span class="mw-page-title-main">Carbon</span> Chemical element, symbol C and atomic number 6

Carbon is a chemical element; it has symbol C and atomic number 6. It is nonmetallic and tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 electrons. It belongs to group 14 of the periodic table. Carbon makes up about 0.025 percent of Earth's crust. Three isotopes occur naturally, 12C and 13C being stable, while 14C is a radionuclide, decaying with a half-life of about 5,730 years. Carbon is one of the few elements known since antiquity.

<span class="mw-page-title-main">Covalent bond</span> Chemical bond by sharing of electron pairs

A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atoms, when they share electrons, is known as covalent bonding. For many molecules, the sharing of electrons allows each atom to attain the equivalent of a full valence shell, corresponding to a stable electronic configuration. In organic chemistry, covalent bonding is much more common than ionic bonding.

<span class="mw-page-title-main">Fullerene</span> Allotrope of carbons

A fullerene is an allotrope of carbon whose molecules consist of carbon atoms connected by single and double bonds so as to form a closed or partially closed mesh, with fused rings of five to seven atoms. The molecules may be hollow spheres, ellipsoids, tubes, or other shapes.

<span class="mw-page-title-main">Molecule</span> Electrically neutral group of two or more atoms

A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and biochemistry, the distinction from ions is dropped and molecule is often used when referring to polyatomic ions.

An attosecond is a unit of time in the International System of Units (SI) equal to 10−18 or 11 000 000 000 000 000 000 of a second. An attosecond is to a second as a second is to about 31.71 billion years. The attosecond is a newly discovered "slice of time" that is tiny but has various potential applications: it can observe oscillating molecules, the chemical bonds formed by atoms in chemical reactions, and other extremely tiny and extremely fast things.

<span class="mw-page-title-main">Allotropes of carbon</span> Materials made only out of carbon

Carbon is capable of forming many allotropes due to its valency. Well-known forms of carbon include diamond and graphite. In recent decades, many more allotropes have been discovered and researched, including ball shapes such as buckminsterfullerene and sheets such as graphene. Larger-scale structures of carbon include nanotubes, nanobuds and nanoribbons. Other unusual forms of carbon exist at very high temperatures or extreme pressures. Around 500 hypothetical 3‑periodic allotropes of carbon are known at the present time, according to the Samara Carbon Allotrope Database (SACADA).

<span class="mw-page-title-main">Catenation</span> Bonding of atoms of the same element into chains or rings

In chemistry, catenation is the bonding of atoms of the same element into a series, called a chain. A chain or a ring shape may be open if its ends are not bonded to each other, or closed if they are bonded in a ring. The words to catenate and catenation reflect the Latin root catena, "chain".

<span class="mw-page-title-main">VSEPR theory</span> Model for predicting molecular geometry

Valence shell electron pair repulsion (VSEPR) theory, is a model used in chemistry to predict the geometry of individual molecules from the number of electron pairs surrounding their central atoms. It is also named the Gillespie-Nyholm theory after its two main developers, Ronald Gillespie and Ronald Nyholm.

<span class="mw-page-title-main">Endohedral fullerene</span> Fullerene molecule with additional atoms, ions, or clusters enclosed within itself

Endohedral fullerenes, also called endofullerenes, are fullerenes that have additional atoms, ions, or clusters enclosed within their inner spheres. The first lanthanum C60 complex called La@C60 was synthesized in 1985. The @ (at sign) in the name reflects the notion of a small molecule trapped inside a shell. Two types of endohedral complexes exist: endohedral metallofullerenes and non-metal doped fullerenes.

<span class="mw-page-title-main">Polyyne</span> Any organic compound with alternating C–C and C≡C bonds

A polyyne is any organic compound with alternating single and triple bonds; that is, a series of consecutive alkynes, (−C≡C−)n with n greater than 1. These compounds are also called polyacetylenes, especially in the natural products and chemical ecology literature, even though this nomenclature more properly refers to acetylene polymers composed of alternating single and double bonds (−CR=CR′−)n with n greater than 1. They are also sometimes referred to as oligoynes, or carbinoids after "carbyne" (−C≡C−), the hypothetical allotrope of carbon that would be the ultimate member of the series. The synthesis of this substance has been claimed several times since the 1960s, but those reports have been disputed. Indeed, the substances identified as short chains of "carbyne" in many early organic synthesis attempts would be called polyynes today.

A carbon–nitrogen bond is a covalent bond between carbon and nitrogen and is one of the most abundant bonds in organic chemistry and biochemistry.

<span class="mw-page-title-main">Allotropes of sulfur</span> Class of substances

The element sulfur exists as many allotropes. In number of allotropes, sulfur is second only to carbon. In addition to the allotropes, each allotrope often exists in polymorphs delineated by Greek prefixes.

<span class="mw-page-title-main">Linear acetylenic carbon</span> Polymer made of repeating −C≡C− units

Linear acetylenic carbon (LAC), also known as carbyne or Linear Carbon Chain (LCC), is an allotrope of carbon that has the chemical structure (−C≡C−)n as a repeat unit, with alternating single and triple bonds. It would thus be the ultimate member of the polyyne family.

Molecular scale electronics, also called single-molecule electronics, is a branch of nanotechnology that uses single molecules, or nanoscale collections of single molecules, as electronic components. Because single molecules constitute the smallest stable structures imaginable, this miniaturization is the ultimate goal for shrinking electrical circuits.

<span class="mw-page-title-main">Disilyne</span> Chemical compound

Disilyne is a silicon hydride with the formula Si
2
H
2
. Several isomers are possible, but none are sufficiently stable to be of practical value. Substituted disilynes contain a formal silicon–silicon triple bond and as such are sometimes written R2Si2 (where R is a substituent group). They are the silicon analogues of alkynes.

<span class="mw-page-title-main">Benzotriyne</span> Hypothetical molecule; 6-sided ring composed of pure carbon

Benzotriyne or cyclo[6]carbon is a hypothetical compound, an allotrope of carbon with molecular formula C6. The molecule is a ring of six carbon atoms, connected by alternating triple and single bonds. It is, therefore, a potential member of the cyclo[n]carbon family.

In organic chemistry, a cyclo[n]carbon is a chemical compound consisting solely of a number n of carbon atoms covalently linked in a ring. Since the compounds are composed only of carbon atoms, they are allotropes of carbon. Possible bonding patterns include all double bonds or alternating single bonds and triple bonds.

<span class="mw-page-title-main">Tetranitrogen</span> Chemical compound

Tetranitrogen is a neutrally charged polynitrogen allotrope of the chemical formula N
4
and consists of four nitrogen atoms. The tetranitrogen cation is the positively charged ion, N+
4
, which is more stable than the neutral tetranitrogen molecule and is thus more studied.

<span class="mw-page-title-main">Graphyne</span> Allotrope of carbon

Graphyne is an allotrope of carbon. Its structure is one-atom-thick planar sheets of sp and sp2-bonded carbon atoms arranged in crystal lattice. It can be seen as a lattice of benzene rings connected by acetylene bonds. The material is called graphyne-n when benzene rings are connected by n sequential acetylene molecules, and graphdiyne for a particular case of n = 2.

<span class="mw-page-title-main">Carbon nanohoop</span>

Carbon nanohoops are a class of molecules consisting of aromatic sections curved out of planarity by the inherent cyclic geometry of the molecule. This class of molecules came into existence with the synthesis of cycloparaphenylenes by Ramesh Jasti in the lab of Carolyn Bertozzi and since then has been expanded into cyclonaphthylenes, cyclochrysenylenes, and even cyclohexabenzocoronenylenes. Moreover, several nanohoops containing such antiaromatic units as dibenzo[a,e]pentalene and pyrrolo[3,2-b]pyrrole are reported. Carbon nanohoops often map on to a certain chirality of carbon nanotube. If the diameter is adequate, these molecules can host a fullerene. For example, [10]cycloparaphenylene can host a C60 fullerene.

References

  1. George A. Adamson; Charles W. Rees (1996). "Towards the total synthesis of cyclo[n]carbons and the generation of cyclo[6]carbon". J. Chem. Soc., Perkin Trans. 1 (13): 1535–1543. doi:10.1039/P19960001535.
  2. François Diederich; Yves Rubin; Carolyn B. Knobler; Robert L. Whetten; Kenneth E. Schriver; Kendall N. Houk; Yi Li (8 September 1989). "All-Carbon Molecules: Evidence for the Generation of Cyclo[18]carbon from a Stable Organic Precursor". Science. 245 (4922): 1088–1090. Bibcode:1989Sci...245.1088D. doi:10.1126/science.245.4922.1088. PMID   17838807. S2CID   23726682.
  3. Kaiser, Katharina; Scriven, Lorel M.; Schulz, Fabian; Gawel, Przemyslaw; Gross, Leo; Anderson, Harry L. (15 Aug 2019). "An sp-hybridized molecular carbon allotrope, cyclo[18]carbon". Science. 365 (6459): 1299–1301. arXiv: 1908.05904 . doi:10.1126/science.aay1914. PMID   31416933. S2CID   201019470.
  4. 1 2 Castelvecchi, Davide (15 August 2019). "Chemists make first-ever ring of pure carbon". Nature. 572 (7770): 426. doi: 10.1038/d41586-019-02473-z . PMID   31431741.
  5. Stasyuk, Anton J.; Stasyuk, Olga A.; Solà, Miquel; Voityuk, Alexander A. (29 Nov 2019). "Cyclo[18]carbon: the smallest all-carbon electron acceptor". Chemical Communications. 56 (3): 352–355. doi:10.1039/c9cc08399e. hdl: 10256/17613 . PMID   31825030. S2CID   209316603.