An ab initio study of the mechanism of the cycloaddition reaction forming bicyclic compounds between vinylidene (H2C=C:) and ethylene
The mechanism of the cycloaddition reaction forming a bicyclic compounds between singlet vinylidene (H2C=C:) and ethylene was investigated using the CCSD(T)//MP2/6-31G* method. From the potential energy profile, it can be predicted that this reaction has one dominant channel. The presented rule of t...
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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2011-05-01
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| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | http://www.shd.org.rs/JSCS/Vol76/No5/09_4854_4155.pdf |
| _version_ | 1818232848184770560 |
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| author | YONGQING LI ZHENXIA LIAN XIUHUI LU |
| author_facet | YONGQING LI ZHENXIA LIAN XIUHUI LU |
| author_sort | YONGQING LI |
| collection | DOAJ |
| description | The mechanism of the cycloaddition reaction forming a bicyclic compounds between singlet vinylidene (H2C=C:) and ethylene was investigated using the CCSD(T)//MP2/6-31G* method. From the potential energy profile, it can be predicted that this reaction has one dominant channel. The presented rule of this reaction, a [2+2] cycloaddition reaction between the two reactants occurred forming a four-membered ring carbene (INT1), in which the sp lone electron of the C atom from carbene in INT1 and the π* unoccupied orbital of ethane form the sp®π* donor–acceptor effect, resulting in the formation of intermediate (INT2). Due to the further sp3 hybridization of C atom from carbene in INT1, INT2 isomerizes to the bicyclic compound (P2) via the transition state (TS2). |
| first_indexed | 2024-12-12T11:12:48Z |
| format | Article |
| id | doaj.art-87d888cba2a748be92e1ba52ed43d466 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 |
| language | English |
| last_indexed | 2024-12-12T11:12:48Z |
| publishDate | 2011-05-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-87d888cba2a748be92e1ba52ed43d4662022-12-22T00:26:14ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51392011-05-01765743749An ab initio study of the mechanism of the cycloaddition reaction forming bicyclic compounds between vinylidene (H2C=C:) and ethyleneYONGQING LIZHENXIA LIANXIUHUI LUThe mechanism of the cycloaddition reaction forming a bicyclic compounds between singlet vinylidene (H2C=C:) and ethylene was investigated using the CCSD(T)//MP2/6-31G* method. From the potential energy profile, it can be predicted that this reaction has one dominant channel. The presented rule of this reaction, a [2+2] cycloaddition reaction between the two reactants occurred forming a four-membered ring carbene (INT1), in which the sp lone electron of the C atom from carbene in INT1 and the π* unoccupied orbital of ethane form the sp®π* donor–acceptor effect, resulting in the formation of intermediate (INT2). Due to the further sp3 hybridization of C atom from carbene in INT1, INT2 isomerizes to the bicyclic compound (P2) via the transition state (TS2).http://www.shd.org.rs/JSCS/Vol76/No5/09_4854_4155.pdfvinylidenereaction mechanismpotential energy surface |
| spellingShingle | YONGQING LI ZHENXIA LIAN XIUHUI LU An ab initio study of the mechanism of the cycloaddition reaction forming bicyclic compounds between vinylidene (H2C=C:) and ethylene Journal of the Serbian Chemical Society vinylidene reaction mechanism potential energy surface |
| title | An ab initio study of the mechanism of the cycloaddition reaction forming bicyclic compounds between vinylidene (H2C=C:) and ethylene |
| title_full | An ab initio study of the mechanism of the cycloaddition reaction forming bicyclic compounds between vinylidene (H2C=C:) and ethylene |
| title_fullStr | An ab initio study of the mechanism of the cycloaddition reaction forming bicyclic compounds between vinylidene (H2C=C:) and ethylene |
| title_full_unstemmed | An ab initio study of the mechanism of the cycloaddition reaction forming bicyclic compounds between vinylidene (H2C=C:) and ethylene |
| title_short | An ab initio study of the mechanism of the cycloaddition reaction forming bicyclic compounds between vinylidene (H2C=C:) and ethylene |
| title_sort | ab initio study of the mechanism of the cycloaddition reaction forming bicyclic compounds between vinylidene h2c c and ethylene |
| topic | vinylidene reaction mechanism potential energy surface |
| url | http://www.shd.org.rs/JSCS/Vol76/No5/09_4854_4155.pdf |
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