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A theoretical study of the solvent effect on Diels-Alder reaction in room temperature ionic liquids using a supermolecular approach
The Diels-Alder reaction between cyclopentadiene and three dienophiles (acrolein, methyl acrylate and acrylonitrile) in different room temperature ionic liquids containing imidazolium-based cations ([HBIM] + , [BMIM] + and [BM 2 IM] + ) has been studied at the DFT level using a supermolecular approa...
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| Published in: | Theoretical chemistry accounts 2009-06, Vol.123 (3-4), p.347-352 |
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| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c331t-a21cd510bf0eab0be4352bfd7bbed914321552127bc9e3698de548f3807138633 |
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| cites | cdi_FETCH-LOGICAL-c331t-a21cd510bf0eab0be4352bfd7bbed914321552127bc9e3698de548f3807138633 |
| container_end_page | 352 |
| container_issue | 3-4 |
| container_start_page | 347 |
| container_title | Theoretical chemistry accounts |
| container_volume | 123 |
| creator | Bini, Riccardo Chiappe, Cinzia Mestre, Veronica L. Pomelli, Christian S. Welton, Thomas |
| description | The Diels-Alder reaction between cyclopentadiene and three dienophiles (acrolein, methyl acrylate and acrylonitrile) in different room temperature ionic liquids containing imidazolium-based cations ([HBIM]
+
, [BMIM]
+
and [BM
2
IM]
+
) has been studied at the DFT level using a supermolecular approach. An analysis of the theoretical results shows that the ionic liquid cation coordination affects the equilibrium geometries and electronic structures of the reacting species throughout the reaction pathway leading to changes in reactivity and selectivity. They also indicate that the strong asynchronicity of the Diels-Alder reactions in ionic liquids is due to the polarisation effect of the cation. |
| doi_str_mv | 10.1007/s00214-009-0525-0 |
| format | article |
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+
, [BMIM]
+
and [BM
2
IM]
+
) has been studied at the DFT level using a supermolecular approach. An analysis of the theoretical results shows that the ionic liquid cation coordination affects the equilibrium geometries and electronic structures of the reacting species throughout the reaction pathway leading to changes in reactivity and selectivity. They also indicate that the strong asynchronicity of the Diels-Alder reactions in ionic liquids is due to the polarisation effect of the cation.</description><identifier>ISSN: 1432-881X</identifier><identifier>EISSN: 1432-2234</identifier><identifier>DOI: 10.1007/s00214-009-0525-0</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer-Verlag</publisher><subject>Atomic/Molecular Structure and Spectra ; Chemistry ; Chemistry and Materials Science ; Inorganic Chemistry ; Organic Chemistry ; Physical Chemistry ; Regular Article ; Theoretical and Computational Chemistry</subject><ispartof>Theoretical chemistry accounts, 2009-06, Vol.123 (3-4), p.347-352</ispartof><rights>Springer-Verlag 2009</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c331t-a21cd510bf0eab0be4352bfd7bbed914321552127bc9e3698de548f3807138633</citedby><cites>FETCH-LOGICAL-c331t-a21cd510bf0eab0be4352bfd7bbed914321552127bc9e3698de548f3807138633</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27911,27912</link.rule.ids></links><search><creatorcontrib>Bini, Riccardo</creatorcontrib><creatorcontrib>Chiappe, Cinzia</creatorcontrib><creatorcontrib>Mestre, Veronica L.</creatorcontrib><creatorcontrib>Pomelli, Christian S.</creatorcontrib><creatorcontrib>Welton, Thomas</creatorcontrib><title>A theoretical study of the solvent effect on Diels-Alder reaction in room temperature ionic liquids using a supermolecular approach</title><title>Theoretical chemistry accounts</title><addtitle>Theor Chem Acc</addtitle><description>The Diels-Alder reaction between cyclopentadiene and three dienophiles (acrolein, methyl acrylate and acrylonitrile) in different room temperature ionic liquids containing imidazolium-based cations ([HBIM]
+
, [BMIM]
+
and [BM
2
IM]
+
) has been studied at the DFT level using a supermolecular approach. An analysis of the theoretical results shows that the ionic liquid cation coordination affects the equilibrium geometries and electronic structures of the reacting species throughout the reaction pathway leading to changes in reactivity and selectivity. They also indicate that the strong asynchronicity of the Diels-Alder reactions in ionic liquids is due to the polarisation effect of the cation.</description><subject>Atomic/Molecular Structure and Spectra</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Inorganic Chemistry</subject><subject>Organic Chemistry</subject><subject>Physical Chemistry</subject><subject>Regular Article</subject><subject>Theoretical and Computational Chemistry</subject><issn>1432-881X</issn><issn>1432-2234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNp9kM1OwzAQhC0EEqXwANz8Agb_xE1yrMqvhMQFJG6W46xbV0kcbAepZ14cR-2Z065GM6udD6FbRu8YpeV9pJSzglBaEyq5JPQMLVghOOFcFOenvarY1yW6inFPs53LcoF-1zjtwAdIzugOxzS1B-ztLOLoux8YEgZrwSTsB_zgoItk3bUQcABtksuiG3DwvscJ-hGCTlMAnHVncOe-J9dGPEU3bLHGccqG3ndgpk4HrMcxeG121-jC6i7CzWku0efT48fmhby9P79u1m_ECMES0ZyZVjLaWAq6oQ0UQvLGtmXTQFvPBZmUnPGyMTWIVV21IIvKioqWTFQrIZaIHe-a4GMMYNUYXK_DQTGqZorqSFFlimqmqGjO8GMmZu-whaD2fgpDfvOf0B_oQ3el</recordid><startdate>20090601</startdate><enddate>20090601</enddate><creator>Bini, Riccardo</creator><creator>Chiappe, Cinzia</creator><creator>Mestre, Veronica L.</creator><creator>Pomelli, Christian S.</creator><creator>Welton, Thomas</creator><general>Springer-Verlag</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20090601</creationdate><title>A theoretical study of the solvent effect on Diels-Alder reaction in room temperature ionic liquids using a supermolecular approach</title><author>Bini, Riccardo ; Chiappe, Cinzia ; Mestre, Veronica L. ; Pomelli, Christian S. ; Welton, Thomas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c331t-a21cd510bf0eab0be4352bfd7bbed914321552127bc9e3698de548f3807138633</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Atomic/Molecular Structure and Spectra</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Inorganic Chemistry</topic><topic>Organic Chemistry</topic><topic>Physical Chemistry</topic><topic>Regular Article</topic><topic>Theoretical and Computational Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bini, Riccardo</creatorcontrib><creatorcontrib>Chiappe, Cinzia</creatorcontrib><creatorcontrib>Mestre, Veronica L.</creatorcontrib><creatorcontrib>Pomelli, Christian S.</creatorcontrib><creatorcontrib>Welton, Thomas</creatorcontrib><collection>CrossRef</collection><jtitle>Theoretical chemistry accounts</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bini, Riccardo</au><au>Chiappe, Cinzia</au><au>Mestre, Veronica L.</au><au>Pomelli, Christian S.</au><au>Welton, Thomas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A theoretical study of the solvent effect on Diels-Alder reaction in room temperature ionic liquids using a supermolecular approach</atitle><jtitle>Theoretical chemistry accounts</jtitle><stitle>Theor Chem Acc</stitle><date>2009-06-01</date><risdate>2009</risdate><volume>123</volume><issue>3-4</issue><spage>347</spage><epage>352</epage><pages>347-352</pages><issn>1432-881X</issn><eissn>1432-2234</eissn><abstract>The Diels-Alder reaction between cyclopentadiene and three dienophiles (acrolein, methyl acrylate and acrylonitrile) in different room temperature ionic liquids containing imidazolium-based cations ([HBIM]
+
, [BMIM]
+
and [BM
2
IM]
+
) has been studied at the DFT level using a supermolecular approach. An analysis of the theoretical results shows that the ionic liquid cation coordination affects the equilibrium geometries and electronic structures of the reacting species throughout the reaction pathway leading to changes in reactivity and selectivity. They also indicate that the strong asynchronicity of the Diels-Alder reactions in ionic liquids is due to the polarisation effect of the cation.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer-Verlag</pub><doi>10.1007/s00214-009-0525-0</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1432-881X |
| ispartof | Theoretical chemistry accounts, 2009-06, Vol.123 (3-4), p.347-352 |
| issn | 1432-881X 1432-2234 |
| language | eng |
| recordid | cdi_crossref_primary_10_1007_s00214_009_0525_0 |
| source | Springer Nature |
| subjects | Atomic/Molecular Structure and Spectra Chemistry Chemistry and Materials Science Inorganic Chemistry Organic Chemistry Physical Chemistry Regular Article Theoretical and Computational Chemistry |
| title | A theoretical study of the solvent effect on Diels-Alder reaction in room temperature ionic liquids using a supermolecular approach |
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