Vinylene group

In chemistry, vinylene (also ethenylene or 1,2-ethenediyl)^[1] is a divalent functional group (a part of a molecule)^[2] with formula −CH=CH−;^[3] namely, two carbons, each connected to the other by a double bond, to an hydrogen atom by a single bond, and to the rest of the molecule by another single bond.^[4]^[5]

This group can be viewed as a molecule of ethene (ethylene, H₂C=CH₂) with an hydrogen removed from each carbon; or a vinyl group −CH=CH₂ with one hydrogen removed from the terminal carbon.^[6]^[7]^[8] It should not be confused with the vinylidene group =C=CH₂ or >C=CH₂.

A vinylene unit attached to two distinct atoms other than hydrogen (namely R−CH=CH−R') is a source of cis-trans isomerism.^[9]^[10]

The vinylene group is the repeating unit in polyacetylene and in polyenes.^[11]

References

^ Liu, Qibo; Burton, Donald J. (2002-05-02). "Stereoselective preparation of (E)-(1,2-difluoro-1,2-ethenediyl) bis[tributylstannane] and stereospecific synthesis of (E)-1,2-difluorostilbenes". Organic Letters. 4 (9): 1483–1485. doi:10.1021/ol025686+. ISSN 1523-7060. PMID 11975609.
^ Blockhuys, null; Claes, null; Van Grieken R, null; Geise, null (2000-07-15). "Assessing the molecular weight of a conducting polymer by grazing emission XRF". Analytical Chemistry. 72 (14): 3366–3368. doi:10.1021/ac990877k. ISSN 1520-6882. PMID 10939413.
^ Ryskulova, Kanykei; Rao Gulur Srinivas, Anupama; Kerr-Phillips, Thomas; Peng, Hui; Barker, David; Travas-Sejdic, Jadranka; Hoogenboom, Richard (2016-10-18). "Multiresponsive Behavior of Functional Poly(p-phenylene vinylene)s in Water". Polymers. 8 (10): E365. doi:10.3390/polym8100365. ISSN 2073-4360. PMC 6432201. PMID 30974643.
^ Wang, Dengxu; Xue, Lei; Li, Liguo; Deng, Bei; Feng, Shengyu; Liu, Hongzhi; Zhao, Xian (2013-05-27). "Rational design and synthesis of hybrid porous polymers derived from polyhedral oligomeric silsesquioxanes via heck coupling reactions". Macromolecular Rapid Communications. 34 (10): 861–866. doi:10.1002/marc.201200835. ISSN 1521-3927. PMID 23529823.
^ Sasidharan, Manickam; Bhaumik, Asim (2013-04-10). "Novel and mild synthetic strategy for the sulfonic Acid functionalization in periodic mesoporous ethenylene-silica". ACS Applied Materials & Interfaces. 5 (7): 2618–2625. doi:10.1021/am4000326. ISSN 1944-8252. PMID 23484521.
^ Reichert, Edward. "Ethylene bichloride as an anæsthetic agent: with a consideration of ethylene methylethylate, ethylene ethylate, ethyl nitrate, and ethylidene bichloride". National Library of Medicine. Retrieved 2022-09-28.
^ "Chemical warfare agents and related chemical problems". National Library of Medicine. 14111270RX1. 1946. Retrieved 2022-09-28.
^ Mukherjee, Soumya (2019-01-01). "Recent advancements in the mechanism of nitric oxide signaling associated with hydrogen sulfide and melatonin crosstalk during ethylene-induced fruit ripening in plants". Nitric Oxide: Biology and Chemistry. 82: 25–34. doi:10.1016/j.niox.2018.11.003. ISSN 1089-8611. PMID 30465876. S2CID 53753053.
^ Valentini, Alessio; Rivero, Daniel; Zapata, Felipe; García-Iriepa, Cristina; Marazzi, Marco; Palmeiro, Raúl; Fdez Galván, Ignacio; Sampedro, Diego; Olivucci, Massimo; Frutos, Luis Manuel (2017-03-27). "Optomechanical Control of Quantum Yield in Trans-Cis Ultrafast Photoisomerization of a Retinal Chromophore Model". Angewandte Chemie International Edition. 56 (14): 3842–3846. doi:10.1002/anie.201611265. ISSN 1521-3773. PMID 28251753.
^ Georgiev, Anton; Kostadinov, Anton; Ivanov, Deyan; Dimov, Deyan; Stoyanov, Simeon; Nedelchev, Lian; Nazarova, Dimana; Yancheva, Denitsa (2018-03-01). "Synthesis, spectroscopic and TD-DFT quantum mechanical study of azo-azomethine dyes. A laser induced trans-cis-trans photoisomerization cycle". Spectrochimica Acta Part A: Molecular Spectroscopy. 192: 263–274. Bibcode:2018AcSpA.192..263G. doi:10.1016/j.saa.2017.11.016. PMID 29156313.
^ Johnston, Dean H.; Gao, Lei; Lonergan, Mark C. (2010-03-23). "Kinetic Study of the Ring-Opening Metathesis Copolymerization of Ionic with Nonionic Cyclooctatetraene Derivatives To Yield Polyacetylene Ionomers". Macromolecules. 43 (6): 2676–2683. Bibcode:2010MaMol..43.2676J. doi:10.1021/ma100034h. ISSN 0024-9297.

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[1] Liu, Qibo; Burton, Donald J. (2002-05-02). "Stereoselective preparation of (E)-(1,2-difluoro-1,2-ethenediyl) bis[tributylstannane] and stereospecific synthesis of (E)-1,2-difluorostilbenes". Organic Letters. 4 (9): 1483–1485. doi:10.1021/ol025686+. ISSN 1523-7060. PMID 11975609.

[2] Blockhuys, null; Claes, null; Van Grieken R, null; Geise, null (2000-07-15). "Assessing the molecular weight of a conducting polymer by grazing emission XRF". Analytical Chemistry. 72 (14): 3366–3368. doi:10.1021/ac990877k. ISSN 1520-6882. PMID 10939413.

[3] Ryskulova, Kanykei; Rao Gulur Srinivas, Anupama; Kerr-Phillips, Thomas; Peng, Hui; Barker, David; Travas-Sejdic, Jadranka; Hoogenboom, Richard (2016-10-18). "Multiresponsive Behavior of Functional Poly(p-phenylene vinylene)s in Water". Polymers. 8 (10): E365. doi:10.3390/polym8100365. ISSN 2073-4360. PMC 6432201. PMID 30974643.

[4] Wang, Dengxu; Xue, Lei; Li, Liguo; Deng, Bei; Feng, Shengyu; Liu, Hongzhi; Zhao, Xian (2013-05-27). "Rational design and synthesis of hybrid porous polymers derived from polyhedral oligomeric silsesquioxanes via heck coupling reactions". Macromolecular Rapid Communications. 34 (10): 861–866. doi:10.1002/marc.201200835. ISSN 1521-3927. PMID 23529823.

[5] Sasidharan, Manickam; Bhaumik, Asim (2013-04-10). "Novel and mild synthetic strategy for the sulfonic Acid functionalization in periodic mesoporous ethenylene-silica". ACS Applied Materials & Interfaces. 5 (7): 2618–2625. doi:10.1021/am4000326. ISSN 1944-8252. PMID 23484521.

[6] Reichert, Edward. "Ethylene bichloride as an anæsthetic agent: with a consideration of ethylene methylethylate, ethylene ethylate, ethyl nitrate, and ethylidene bichloride". National Library of Medicine. Retrieved 2022-09-28.

[7] "Chemical warfare agents and related chemical problems". National Library of Medicine. 14111270RX1. 1946. Retrieved 2022-09-28.

[8] Mukherjee, Soumya (2019-01-01). "Recent advancements in the mechanism of nitric oxide signaling associated with hydrogen sulfide and melatonin crosstalk during ethylene-induced fruit ripening in plants". Nitric Oxide: Biology and Chemistry. 82: 25–34. doi:10.1016/j.niox.2018.11.003. ISSN 1089-8611. PMID 30465876. S2CID 53753053.

[9] Valentini, Alessio; Rivero, Daniel; Zapata, Felipe; García-Iriepa, Cristina; Marazzi, Marco; Palmeiro, Raúl; Fdez Galván, Ignacio; Sampedro, Diego; Olivucci, Massimo; Frutos, Luis Manuel (2017-03-27). "Optomechanical Control of Quantum Yield in Trans-Cis Ultrafast Photoisomerization of a Retinal Chromophore Model". Angewandte Chemie International Edition. 56 (14): 3842–3846. doi:10.1002/anie.201611265. ISSN 1521-3773. PMID 28251753.

[10] Georgiev, Anton; Kostadinov, Anton; Ivanov, Deyan; Dimov, Deyan; Stoyanov, Simeon; Nedelchev, Lian; Nazarova, Dimana; Yancheva, Denitsa (2018-03-01). "Synthesis, spectroscopic and TD-DFT quantum mechanical study of azo-azomethine dyes. A laser induced trans-cis-trans photoisomerization cycle". Spectrochimica Acta Part A: Molecular Spectroscopy. 192: 263–274. Bibcode:2018AcSpA.192..263G. doi:10.1016/j.saa.2017.11.016. PMID 29156313.

[11] Johnston, Dean H.; Gao, Lei; Lonergan, Mark C. (2010-03-23). "Kinetic Study of the Ring-Opening Metathesis Copolymerization of Ionic with Nonionic Cyclooctatetraene Derivatives To Yield Polyacetylene Ionomers". Macromolecules. 43 (6): 2676–2683. Bibcode:2010MaMol..43.2676J. doi:10.1021/ma100034h. ISSN 0024-9297.

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Vinylene group

See also

References