| Cyclopentadiene | |
|---|---|
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| Other names | pentole, pyropentylene, CPD |
| Identifiers | |
| CAS number | [542-92-7] |
| RTECS number | GY1000000 |
| SMILES | C1C=CC=C1 |
| Properties | |
| Molecular formula | C5H6 |
| Molar mass | 66. CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 10 g/mol |
| Appearance | colourless liquid |
| Density | 0. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 81 g/cm³, liquid |
| Melting point | -85 °C (188 K) |
| Boiling point | 41 °C (314 K) |
| Structure | |
| Molecular shape | envelope structure |
| Hazards | |
| Flash point | 25 °C |
| Related compounds | |
| Related hydrocarbon | Benzene Cyclobutadiene Cyclopentene |
| Related compounds | Dicyclopentadiene |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Cyclopentadiene is a chemical compound with the formula C5H6. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Molecular geometry or molecular structure is the three- Dimensional arrangement of the Atoms that constitute a Molecule. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air In Organic chemistry, a hydrocarbon is an Organic compound consisting entirely of Hydrogen and Carbon. Benzene, or benzol, is an organic Chemical compound and a known Carcinogen with the molecular formula C 6 H 6 Cyclobutadiene is the smallest - Annulene (-annulene an extremely unstable Hydrocarbon having a lifetime shorter than five seconds in the free state Cyclopentene is a Chemical compound with the formula 58 It is a colorless Liquid with a Petrol -like Odor. Dicyclopentadiene, abbreviated DCPD, is the Chemical compound with the formula C10H12 In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes This colorless liquid organic chemical has a strong and unpleasant odor. Organic chemistry is a discipline within Chemistry which involves the scientific study of the structure properties composition reactions, and preparation A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. At room temperature, this cyclic diene dimerizes over the course of hours to give dicyclopentadiene via a Diels-Alder reaction. Dienes or diolefins are Hydrocarbons which contain two double bonds. A dimer is a Chemical or Biological entity consisting of two subunits called Monomers which are held together by either Intramolecular forces Dicyclopentadiene, abbreviated DCPD, is the Chemical compound with the formula C10H12 The Diels-Alder reaction is an Organic chemical reaction (specifically a Cycloaddition) between a conjugated Diene and a substituted Alkene, This dimer "cracks" to give the monomer upon heating.
The compound is the precursor to the popular cyclopentadienyl-ligand ('Cp') in cyclopentadienyl complexes in organometallic chemistry. In Chemistry, a ligand is either an Atom, Ion, or Molecule (see also Functional group) that bonds to a central metal generally A cyclopentadienyl complex is a Metal complex with one or more cyclopentadienyl groups (C5H5&minus abbreviated as Cp Organometallic chemistry is the study of Chemical compounds containing bonds between Carbon and a Metal. Both cyclopentadiene and dicyclopentadiene can serve as ligands as well, but these are uncommon.
Contents |
Properties
The hydrogen atoms in cyclopentadiene undergo rapid [1,5]-sigmatropic shifts as indicated by the variable temperature1H NMR spectra recorded at various temperatures. A Sigmatropic reaction in Organic chemistry is a Pericyclic reaction wherein the net result is one Sigma bond changed to another sigma bond. [1]
Reactivity of cyclopentadiene
Cyclopentadiene readily undergoes Diels-Alder reactions with dienophiles, such as 1,4-benzoquinone. The Diels-Alder reaction is an Organic chemical reaction (specifically a Cycloaddition) between a conjugated Diene and a substituted Alkene, The Diels-Alder reaction is an Organic chemical reaction (specifically a Cycloaddition) between a conjugated Diene and a substituted Alkene, [2]
The compound is weakly acidic, which is unusual for a hydrocarbon. In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are In Organic chemistry, a hydrocarbon is an Organic compound consisting entirely of Hydrogen and Carbon. This relatively high acidity is explained by the stability of the aromatic, anionic, 5-membered ring (cyclopentadienyl anion, C5H5−). An ion is an Atom or Molecule which has lost or gained one or more Valence electrons giving it a positive or negative electrical charge Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Derivatives of this anion are often depicted as salts, although the free anion does not exist in any appreciable extent in solution. Deprotonation can be achieved, e. Deprotonation is a Chemistry term that refers to the removal of a Proton ( Hydrogen Cation H+ from a Molecule, forming g. by alkali metal bases. The anion serves as a weak nucleophile in organic synthesis and combines with numerous anhydrous halides of the transition metals to form cyclopentadienyl complexes, such as metallocenes. Organic synthesis is a special branch of Chemical synthesis and is concerned with the construction of Organic compounds via Organic reactions Organic In Chemistry, the term transition metal (sometimes also called a transition element) has two possible meanings It commonly refers to any element in A cyclopentadienyl complex is a Metal complex with one or more cyclopentadienyl groups (C5H5&minus abbreviated as Cp A metallocene is a compound with the general formula (C5R52M consisting of two cyclopentadienyl anions (Cp bound to a metal center in the oxidation [3]
Uses
Aside from its use as a synthetic intermediate, cyclopentadiene itself has few applications because it reverts so readily to dicyclopentadiene. Cyclopentadiene reacts with linseed oil to facilitate "drying" upon contact with oxygen. Linseed oil, also known as flax seed oil or simply flax oil, is a clear to yellowish Drying oil derived from the dried ripe seeds of the Flax
See also
- Aromaticity
- Methylcyclopentadiene and pentamethylcyclopentadiene, also found as ligands in organometallic chemistry
References
- ^ Streitwieser, A. Methylcyclopentadiene describes three isomeric cyclic di Olefins with the formula C5MeH5 (Me = CH3 12345-Pentamethylcyclopentadiene is a cyclic diolefin with the formula C5Me5H (Me = CH3 ; Heathcock, C. H.; Kosower, E. Clayton Heathcock is an organic chemist, Professor of Chemistry and Dean of the College of Chemistry at the University of California Berkeley. M. (1998). Introduction to Organic Chemistry (4th Edn. ) Upper Saddle River, NJ: Prentice Hall.
- ^ Masaji Oda, Takeshi Kawase, Tomoaki Okada, and Tetsuya Enomoto "2-Cyclohexene-1,4-dione" Organic Syntheses, Collected Volume 9, p. 186 (1998). http://www.orgsyn.org/orgsyn/pdfs/CV9P0186.pdf
- ^ Girolami, G. S. ; Rauchfuss, T. B. and Angelici, R. J. , Synthesis and Technique in Inorganic Chemistry, University Science Books: Mill Valley, CA, 1999. ISBN 0935702482
External links
Dictionary
cyclopentadiene
-noun
- (organic chemistry) an unsaturated alicyclic hydrocarbon, C5H6; it forms complexes with some transition elements
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