Penguinone

Last updated
Penguinone
Skeletal formula of penguinone Penguinone.svg
Skeletal formula of penguinone
Space-filling model of the penguinone molecule Penguinone-3D-spacefill.png
Space-filling model of the penguinone molecule
Names
Preferred IUPAC name
3,4,4,5-Tetramethylcyclohexa-2,5-dien-1-one
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C10H14O/c1-7-5-9(11)6-8(2)10(7,3)4/h5-6H,1-4H3
    Key: RHIYIMQPIGYWEK-UHFFFAOYSA-N
  • InChI=1/C10H14O/c1-7-5-9(11)6-8(2)10(7,3)4/h5-6H,1-4H3
    Key: RHIYIMQPIGYWEK-UHFFFAOYAI
  • CC1=CC(=O)C=C(C1(C)C)C
Properties
C10H14O
Molar mass 150.221 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Penguinone is an organic compound with the molecular formula C
10
H
14
O
. Its name comes from the fact that its 2-dimensional molecular structure resembles a penguin. [1] [2]

The suffix "-one" indicates that it is a ketone. [3] The systematic name of the molecule is 3,4,4,5-tetramethylcyclohexa-2,5-dienone. [4] [5]

Although it is a dienone and thus has the necessary structure for Dienone-Phenol Rearrangement, the methyl groups in positions 3 and 5 of the ring block the movement of the group at position 4, so even the action of trifluoroacetic acid will not cause transformation to a phenol. [6]

See also

Related Research Articles

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Polymer Substance composed of macromolecules with repeating structural units

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Phenol Chemical compound

Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group (−C6H5) bonded to a hydroxy group (−OH). Mildly acidic, it requires careful handling because it can cause chemical burns.

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Gerhard Herzberg German-Canadian physicist and physical chemist

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Polyphenol Class of chemical compounds

Polyphenols are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

Chemical structure An organized way in which molecules are ordered and sorted

A chemical structure determination includes a chemist's specifying the molecular geometry and, when feasible and necessary, the electronic structure of the target molecule or other solid. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together, and can be represented using structural formulae and by molecular models; complete electronic structure descriptions include specifying the occupation of a molecule's molecular orbitals. Structure determination can be applied to a range of targets from very simple molecules, to very complex ones.

VSEPR theory Theoretical model used in chemistry

Valence shell electron pair repulsion theory, or 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. The premise of VSEPR is that the valence electron pairs surrounding an atom tend to repel each other and will, therefore, adopt an arrangement that minimizes this repulsion. This in turn decreases the molecule's energy and increases its stability, which determines the molecular geometry. Gillespie has emphasized that the electron-electron repulsion due to the Pauli exclusion principle is more important in determining molecular geometry than the electrostatic repulsion.

Catechol Chemical compound

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Arsole Chemical compound

Arsole, also called arsenole or arsacyclopentadiene, is an organoarsenic compound with the formula C4H4AsH. It is classified as a metallole and is isoelectronic to and related to pyrrole except that an arsenic atom is substituted for the nitrogen atom. Whereas the pyrrole molecule is planar, the arsole molecule is not, and the hydrogen atom bonded to arsenic extends out of the molecular plane. Arsole is only moderately aromatic, with about 40% the aromaticity of pyrrole. Arsole itself has not been reported in pure form, but several substituted analogs called arsoles exist. Arsoles and more complex arsole derivatives have similar structure and chemical properties to those of phosphole derivatives. When arsole is fused to a benzene ring, this molecule is called arsindole, or benzarsole.

A calixarene is a macrocycle or cyclic oligomer based on a hydroxyalkylation product of a phenol and an aldehyde.

Prismane Chemical compound

Prismane or 'Ladenburg benzene' is a polycyclic hydrocarbon with the formula C6H6. It is an isomer of benzene, specifically a valence isomer. Prismane is far less stable than benzene. The carbon (and hydrogen) atoms of the prismane molecule are arranged in the shape of a six-atom triangular prism—this compound is the parent and simplest member of the prismanes class of molecules. Albert Ladenburg proposed this structure for the compound now known as benzene. The compound was not synthesized until 1973.

4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid (PHBA), is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. 4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its esters, known as parabens, which are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid.

Phenylpropanoid

The phenylpropanoids are a diverse family of organic compounds that are synthesized by plants from the amino acids phenylalanine and tyrosine. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. From 4-coumaroyl-CoA emanates the biosynthesis of myriad natural products including lignols, flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. The coumaroyl component is produced from cinnamic acid.

Chloranil Chemical compound

Chloranil is a quinone with the molecular formula C6Cl4O2. Also known as tetrachloro-1,4-benzoquinone, it is a yellow solid. Like the parent benzoquinone, chloranil is a planar molecule that functions as a mild oxidant.

Hexamethylbenzene chemical compound

Hexamethylbenzene, also known as mellitene, is a hydrocarbon with the molecular formula C12H18 and the condensed structural formula C6(CH3)6. It is an aromatic compound and a derivative of benzene, where benzene's six hydrogen atoms have each been replaced by a methyl group. In 1929 Kathleen Lonsdale reported the crystal structure of hexamethylbenzene, demonstrating that the central ring is hexagonal and flat and thereby ending an ongoing debate about the physical parameters of the benzene system. This was a historically significant result, both for the field of X-ray crystallography and for understanding aromaticity.

Olympicene Chemical compound

Olympicene is an organic carbon based molecule formed of five rings, of which four are benzene rings, joined in the shape of the Olympic rings.

Dienone-phenol rearrangement

The dienone-phenol rearrangement is a reaction in organic chemistry first reported in 1921 by Auwers and Ziegler. A common example of dienone-phenol rearrangement is 4,4-disubstituted de:cyclohexadienone converting into a stable 3,4-disubstituted phenol in presence of acid. A similar rearrangement is possible with 2,2-disubstituted cyclohexadienone to its corresponding disubstituted phenol. Usually this type rearrangement is a spontaneous unless the presence of a dichloromethyl group at 3rd position or 4th position is blocked with any non hydrogen groups.

References

  1. May, Paul (2008). Molecules with Silly or Unusual Names. Imperial College London. p. 35. ISBN   1848162073.
  2. May, Paul (23 October 2014). "Molecules with Silly or Unusual names". University of Bristol . Retrieved 1 December 2014.
  3. Laszlo, Pierre (2004). "Science as Play". American Scientist. 92 (5): 398. doi:10.1511/2004.5.398.
  4. "Chemical structures beginning with P". about.com. Archived from the original on 21 December 2009. Retrieved 1 December 2014.
  5. Parkvall, Mikael (2006). Limits of Language. London: Battlebridge. p. 176. ISBN   1903292042.
  6. Hagenbruch, Bernd; Hünig, Siegfried (1983). "Ein Beitrag zur Dienon-Phenol-Umlagerung". Chemische Berichte (in German). 116: 3884––3894. doi:10.1002/cber.19831161212.