Hydrocarbon compound made of a 5-carbon chain with two single and two double bonds
In organic chemistry, pentadiene is any hydrocarbon with an open chain of five carbons, connected by two single bonds and two double bonds. All those compounds have the same molecular formula C5H8. The inventory of pentadienes include:
1,2-pentadiene, or ethyl allene, H2C=C=CH−CH2−CH3.[1]
1,3-pentadiene, H2C=CH−CH=CH−CH3 with two isomers:[2][3]
cis-1,3-pentadiene.
trans-1,3-pentadiene, also known as piperylene.
1,4-pentadiene, H2C=CH−CH2−CH=CH2.[4]
2,3-pentadiene, H3C−CH=C=CH−CH3, with two enantiomers (R and S).[5]
Well known derivatives containing pentadiene groups include hexadienes, cyclopentadiene, and especially three fatty acids linoleic acid, α-linolenic acid, and arachidonic acid as well as their triglycerides (fats).
^James R. Durig, Stephen Bell, Gamil A. Guirgis (1996): "Infrared and Raman spectra, conformational stability, ab initio calculations and vibrational assignment for 1,2-pentadiene (ethyl allene)". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, volume 52, issue 14, pages 1843-1859.doi:10.1016/S0584-8539(96)01740-0
^Aldo Priola, Sebastiano Cesca, Giuseppe Ferraris, and Mario Bruzzone (1975): "Relative reactivity of cis‐ and trans‐1,3‐pentadiene in the cationic copolymerization with isobutene". Die Makromolekulare Chemie, volume 176, issue 7, pages 1969-1981. doi:10.1002/macp.1975.021760707
^S. Boue and Rangaswamy Srinivasan (1970): "Differences in reactivity between excited states of cis- and trans-1,3-pentadiene". Journal of the American Chemical Association, volume 92, issue 10, pages 3226–3227. doi:10.1021/ja00713a074
^Paul N. Kogerman (1930): "Synthesis of 1,4-pentadiene". Journal of the American Chemical Association, volume 52, issue 12, pages 5060–5065. doi:10.1021/ja01375a064
^Kenneth B. Wiberg, Yi-gui Wang, Shaun M. Wilson, Patrick H. Vaccaro, William L. Jorgensen, T. Daniel Crawford, Micah L. Abrams, James R. Cheeseman, and Mark Luderer (2008): "Optical Rotatory Dispersion of 2,3-Hexadiene and 2,3-Pentadiene". Journal of Physical Chemistry A J. Phys. Chem. A , 112, 2415-2422. doi:10.1021/jp076572o
of pentadienes include: 1,2-pentadiene, or ethyl allene, H2C=C=CH−CH2−CH3. 1,3-pentadiene, H2C=CH−CH=CH−CH3 with two isomers: cis-1,3-pentadiene. trans-1...
598-23-2 Pentadienes: 1,2-Pentadiene, two cis-trans isomers, CAS 591-95-7 1,3 Pentadiene, CAS 504-60-9 (racemic mixture) cis-1,3-Pentadiene or (Z)-1,3-pentadiene...
Piperylene or 1,3-pentadiene is an organic compound with the formula CH3−CH=CH−CH=CH2. It is a volatile, flammable hydrocarbon. It is one of the five positional...
detoxify sorbates by decarboxylation, producing piperylene (1,3-pentadiene). The pentadiene manifests as a typical odor of kerosene or petroleum. In pure...
to detoxify sorbates by decarboxylation, producing trans-1,3-pentadiene. The pentadiene manifests as a typical odor of kerosene or petroleum. Other detoxification...
perfluoro-2-methyl-1,3-butadiene 384-04-3 1,1,3,4,4,5,5,5-octafluoro-1,2-pentadiene 21972-01-0 This list includes substances that boil just above standard...
half-turn about a suitable axis. Another example of a chiral compound is 2,3-pentadiene H 3 C − CH = C = CH − CH 3 {\displaystyle {\ce {H3C-CH=C=CH-CH3}}} a hydrocarbon...
bond of 1,4-pentadiene releases 30.1 kcal/mol of heat, while hydrogenation of the terminal double bond of conjugated (E)-1,3-pentadiene releases only...
with desired sequence pentadiene-acetylene-pentadiene as in symmetrical adduct 4. An equal amount of asymmetric pentadiene-pentadiene-acetylene compound...
around 6 kcal/mol. Comparison of heats of hydrogenation of 1,4-pentadiene and 1,3-pentadiene estimates a slightly more modest value of 3.5 kcal/mol. For...
may be antarafacial or suprafacial. In the example of a [1,5] shift in pentadiene, if there is a suprafacial shift, there is 6 e− moving suprafacially and...
isomeric pentadienes, the allenic 1,2-pentadiene has a heat of formation of 33.6 kcal/mol, compared to 18.1 kcal/mol for (E)-1,3-pentadiene and 25.4 kcal/mol...
carbon backbone, they are sometimes classified in two groups: All feature pentadiene groups. short chain polyunsaturated fatty acids (SC-PUFA), with 18 carbon...
prepare metal allyl complexes. Benson, R. E.; McKusick, B. C. (1958). "1,4-Pentadiene". Organic Syntheses. 38: 78. O'Brien, S.; Fishwick, M.; McDermott, B.;...
Oxa[5]annulene 1,4-Epoxy-1,3-butadiene 5-Oxacyclopenta-1,3-diene 5-Oxacyclo-1,3-pentadiene Furfuran Divinylene oxide Identifiers CAS Number 110-00-9 Y 3D model (JSmol)...
dioxygenation of polyunsaturated fatty acids in lipids containing a cis,cis-1,4-pentadiene into cell signaling agents that serve diverse roles as autocrine signals...
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