High-level Computational Study of the Site-, Facial- and Stereoselectivities for the Diels-Alder Reaction Between o-Benzoquinone and Norbornadiene
Ab initio and DFT quantum chemical calculations have been applied to a study of the Diels-Alder reaction of o-benzoquinone as diene and norbornadiene as dienophile. Transition states for the different reactions are located and activation energies estimated. The prefered exo-À-facial selectivity an...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2000-12-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/5/12/1417/ |
| _version_ | 1818022127620587520 |
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| author | Ronald N. Warrener Martin R. Johnston Davor Margetic |
| author_facet | Ronald N. Warrener Martin R. Johnston Davor Margetic |
| author_sort | Ronald N. Warrener |
| collection | DOAJ |
| description | Ab initio and DFT quantum chemical calculations have been applied to a study of the Diels-Alder reaction of o-benzoquinone as diene and norbornadiene as dienophile. Transition states for the different reactions are located and activation energies estimated. The prefered exo-À-facial selectivity and exo,endo-stereoselectivity exhibited in this cycloaddition are readily predicted using RHF/3-21G or higher levels of calculations. Differences between experimentally observed results and calculations may be explained by the postulation of a second, nonconcerted biradical mechanism leading to formation of hetero Diels-Alder products. |
| first_indexed | 2024-04-14T08:27:14Z |
| format | Article |
| id | doaj.art-95e347310a19417d927dc37c6532ec07 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-14T08:27:14Z |
| publishDate | 2000-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-95e347310a19417d927dc37c6532ec072022-12-22T02:04:01ZengMDPI AGMolecules1420-30492000-12-015121417142810.3390/51201417High-level Computational Study of the Site-, Facial- and Stereoselectivities for the Diels-Alder Reaction Between o-Benzoquinone and NorbornadieneRonald N. WarrenerMartin R. JohnstonDavor MargeticAb initio and DFT quantum chemical calculations have been applied to a study of the Diels-Alder reaction of o-benzoquinone as diene and norbornadiene as dienophile. Transition states for the different reactions are located and activation energies estimated. The prefered exo-À-facial selectivity and exo,endo-stereoselectivity exhibited in this cycloaddition are readily predicted using RHF/3-21G or higher levels of calculations. Differences between experimentally observed results and calculations may be explained by the postulation of a second, nonconcerted biradical mechanism leading to formation of hetero Diels-Alder products.http://www.mdpi.com/1420-3049/5/12/1417/cycloadditioninverse electron-demando-benzoquinonesab initio and DFT calculations |
| spellingShingle | Ronald N. Warrener Martin R. Johnston Davor Margetic High-level Computational Study of the Site-, Facial- and Stereoselectivities for the Diels-Alder Reaction Between o-Benzoquinone and Norbornadiene Molecules cycloaddition inverse electron-demand o-benzoquinones ab initio and DFT calculations |
| title | High-level Computational Study of the Site-, Facial- and Stereoselectivities for the Diels-Alder Reaction Between o-Benzoquinone and Norbornadiene |
| title_full | High-level Computational Study of the Site-, Facial- and Stereoselectivities for the Diels-Alder Reaction Between o-Benzoquinone and Norbornadiene |
| title_fullStr | High-level Computational Study of the Site-, Facial- and Stereoselectivities for the Diels-Alder Reaction Between o-Benzoquinone and Norbornadiene |
| title_full_unstemmed | High-level Computational Study of the Site-, Facial- and Stereoselectivities for the Diels-Alder Reaction Between o-Benzoquinone and Norbornadiene |
| title_short | High-level Computational Study of the Site-, Facial- and Stereoselectivities for the Diels-Alder Reaction Between o-Benzoquinone and Norbornadiene |
| title_sort | high level computational study of the site facial and stereoselectivities for the diels alder reaction between o benzoquinone and norbornadiene |
| topic | cycloaddition inverse electron-demand o-benzoquinones ab initio and DFT calculations |
| url | http://www.mdpi.com/1420-3049/5/12/1417/ |
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