Diastereoselective green synthesis of pyrrolo[1,2-a]quinolines via [3+2] cycloaddition reaction: insights from molecular electron density theory
The [3+2] cycloaddition (32CA) reaction between cyclic azomethine ylide (generated from N -phenacylquinolinium bromide) and N -arylmaleimide, leading to pyrrolo[1,2-a]quinolone, has been investigated using the Molecular Electron Density Theory at the B3LYP/6-311++G(d,p) computational level with D3 c...
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creator | Mohammad-Salim, Haydar Mondal, Asmita de Julián-Ortiz, Jesus Vicente Acharjee, Nivedita |
description | The [3+2] cycloaddition (32CA) reaction between cyclic azomethine ylide (generated from
N
-phenacylquinolinium bromide) and
N
-arylmaleimide, leading to pyrrolo[1,2-a]quinolone, has been investigated using the Molecular Electron Density Theory at the B3LYP/6-311++G(d,p) computational level with D3 correction. This study focuses on the zwitter-ionic type 32CA reaction, highlighting its polar character with the electronic flux from the azomethine ylide to the alkene. The reaction proceeds with complete
endo-
stereoselectivity, and the activation parameters show minimal variations in different solvents, consistent with experimental observations. The activation energy is associated with the depopulation of the N2–C1 and C4–C5 bonding regions, formation of non-bonding electron density at N2 nitrogen and creation of
pseudoradical
centers at C3, C4 and C5. These findings suggest that the formation of new covalent bonds does not occur at the transition states, in line with the presence of non-covalent interactions at the interatomic bonding regions, as revealed by the topological analysis of the Quantum Theory of Atoms-in-Molecules. |
doi_str_mv | 10.1007/s00214-023-03068-8 |
format | Article |
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N
-phenacylquinolinium bromide) and
N
-arylmaleimide, leading to pyrrolo[1,2-a]quinolone, has been investigated using the Molecular Electron Density Theory at the B3LYP/6-311++G(d,p) computational level with D3 correction. This study focuses on the zwitter-ionic type 32CA reaction, highlighting its polar character with the electronic flux from the azomethine ylide to the alkene. The reaction proceeds with complete
endo-
stereoselectivity, and the activation parameters show minimal variations in different solvents, consistent with experimental observations. The activation energy is associated with the depopulation of the N2–C1 and C4–C5 bonding regions, formation of non-bonding electron density at N2 nitrogen and creation of
pseudoradical
centers at C3, C4 and C5. These findings suggest that the formation of new covalent bonds does not occur at the transition states, in line with the presence of non-covalent interactions at the interatomic bonding regions, as revealed by the topological analysis of the Quantum Theory of Atoms-in-Molecules.</description><identifier>ISSN: 1432-881X</identifier><identifier>EISSN: 1432-2234</identifier><identifier>DOI: 10.1007/s00214-023-03068-8</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Atomic/Molecular Structure and Spectra ; Chemistry ; Chemistry and Materials Science ; Covalent bonds ; Cycloaddition ; Electron density ; Electrons ; Inorganic Chemistry ; Nitrogen ; Organic Chemistry ; Organic compounds ; Physical Chemistry ; Quantum theory ; Stereoselectivity ; Theoretical and Computational Chemistry</subject><ispartof>Theoretical chemistry accounts, 2023-12, Vol.142 (12), Article 129</ispartof><rights>The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c270t-85d42048e6fab2085cd42854c9bc057751ff5bb39fc7d7ef9dd9c7dc4bb0ed053</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s00214-023-03068-8$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00214-023-03068-8$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>Mohammad-Salim, Haydar</creatorcontrib><creatorcontrib>Mondal, Asmita</creatorcontrib><creatorcontrib>de Julián-Ortiz, Jesus Vicente</creatorcontrib><creatorcontrib>Acharjee, Nivedita</creatorcontrib><title>Diastereoselective green synthesis of pyrrolo[1,2-a]quinolines via [3+2] cycloaddition reaction: insights from molecular electron density theory</title><title>Theoretical chemistry accounts</title><addtitle>Theor Chem Acc</addtitle><description>The [3+2] cycloaddition (32CA) reaction between cyclic azomethine ylide (generated from
N
-phenacylquinolinium bromide) and
N
-arylmaleimide, leading to pyrrolo[1,2-a]quinolone, has been investigated using the Molecular Electron Density Theory at the B3LYP/6-311++G(d,p) computational level with D3 correction. This study focuses on the zwitter-ionic type 32CA reaction, highlighting its polar character with the electronic flux from the azomethine ylide to the alkene. The reaction proceeds with complete
endo-
stereoselectivity, and the activation parameters show minimal variations in different solvents, consistent with experimental observations. The activation energy is associated with the depopulation of the N2–C1 and C4–C5 bonding regions, formation of non-bonding electron density at N2 nitrogen and creation of
pseudoradical
centers at C3, C4 and C5. These findings suggest that the formation of new covalent bonds does not occur at the transition states, in line with the presence of non-covalent interactions at the interatomic bonding regions, as revealed by the topological analysis of the Quantum Theory of Atoms-in-Molecules.</description><subject>Atomic/Molecular Structure and Spectra</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Covalent bonds</subject><subject>Cycloaddition</subject><subject>Electron density</subject><subject>Electrons</subject><subject>Inorganic Chemistry</subject><subject>Nitrogen</subject><subject>Organic Chemistry</subject><subject>Organic compounds</subject><subject>Physical Chemistry</subject><subject>Quantum theory</subject><subject>Stereoselectivity</subject><subject>Theoretical and Computational Chemistry</subject><issn>1432-881X</issn><issn>1432-2234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kF9LwzAUxYsoOKdfwKeAj1q9Tdo19U3mXxj4oiCMEdL0Zsvomi1pB_0WfmSzTfDNp3su_M45cKLoMoHbBCC_8wA0SWOgLAYGIx7zo2iQpIzGlLL0-FdznnydRmfeLyHwNMsH0fejkb5Fh9Zjjao1WyRzh9gQ3zftAr3xxGqy7p2ztZ0mNzSWs01nGlubBj3ZGkmm7JrOiOpVbWVVmdbYhjiUaifuiWm8mS9aT7SzK7KyoaWrpSP7OhfQCgPR9iS0WdefRyda1h4vfu8w-nx--hi_xpP3l7fxwyRWNIc25lmVUkg5jrQsKfBMhZ9nqSpKBVmeZ4nWWVmyQqu8ylEXVVUEpdKyBKwgY8Po6pC7dnbToW_F0nauCZWC8gJYwXnOAkUPlHLWe4darJ1ZSdeLBMRueXFYXoTlxX55wYOJHUw-wM0c3V_0P64fi7KKhQ</recordid><startdate>20231201</startdate><enddate>20231201</enddate><creator>Mohammad-Salim, Haydar</creator><creator>Mondal, Asmita</creator><creator>de Julián-Ortiz, Jesus Vicente</creator><creator>Acharjee, Nivedita</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20231201</creationdate><title>Diastereoselective green synthesis of pyrrolo[1,2-a]quinolines via [3+2] cycloaddition reaction: insights from molecular electron density theory</title><author>Mohammad-Salim, Haydar ; Mondal, Asmita ; de Julián-Ortiz, Jesus Vicente ; Acharjee, Nivedita</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c270t-85d42048e6fab2085cd42854c9bc057751ff5bb39fc7d7ef9dd9c7dc4bb0ed053</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Atomic/Molecular Structure and Spectra</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Covalent bonds</topic><topic>Cycloaddition</topic><topic>Electron density</topic><topic>Electrons</topic><topic>Inorganic Chemistry</topic><topic>Nitrogen</topic><topic>Organic Chemistry</topic><topic>Organic compounds</topic><topic>Physical Chemistry</topic><topic>Quantum theory</topic><topic>Stereoselectivity</topic><topic>Theoretical and Computational Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mohammad-Salim, Haydar</creatorcontrib><creatorcontrib>Mondal, Asmita</creatorcontrib><creatorcontrib>de Julián-Ortiz, Jesus Vicente</creatorcontrib><creatorcontrib>Acharjee, Nivedita</creatorcontrib><collection>CrossRef</collection><jtitle>Theoretical chemistry accounts</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mohammad-Salim, Haydar</au><au>Mondal, Asmita</au><au>de Julián-Ortiz, Jesus Vicente</au><au>Acharjee, Nivedita</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diastereoselective green synthesis of pyrrolo[1,2-a]quinolines via [3+2] cycloaddition reaction: insights from molecular electron density theory</atitle><jtitle>Theoretical chemistry accounts</jtitle><stitle>Theor Chem Acc</stitle><date>2023-12-01</date><risdate>2023</risdate><volume>142</volume><issue>12</issue><artnum>129</artnum><issn>1432-881X</issn><eissn>1432-2234</eissn><abstract>The [3+2] cycloaddition (32CA) reaction between cyclic azomethine ylide (generated from
N
-phenacylquinolinium bromide) and
N
-arylmaleimide, leading to pyrrolo[1,2-a]quinolone, has been investigated using the Molecular Electron Density Theory at the B3LYP/6-311++G(d,p) computational level with D3 correction. This study focuses on the zwitter-ionic type 32CA reaction, highlighting its polar character with the electronic flux from the azomethine ylide to the alkene. The reaction proceeds with complete
endo-
stereoselectivity, and the activation parameters show minimal variations in different solvents, consistent with experimental observations. The activation energy is associated with the depopulation of the N2–C1 and C4–C5 bonding regions, formation of non-bonding electron density at N2 nitrogen and creation of
pseudoradical
centers at C3, C4 and C5. These findings suggest that the formation of new covalent bonds does not occur at the transition states, in line with the presence of non-covalent interactions at the interatomic bonding regions, as revealed by the topological analysis of the Quantum Theory of Atoms-in-Molecules.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><doi>10.1007/s00214-023-03068-8</doi></addata></record> |
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subjects | Atomic/Molecular Structure and Spectra Chemistry Chemistry and Materials Science Covalent bonds Cycloaddition Electron density Electrons Inorganic Chemistry Nitrogen Organic Chemistry Organic compounds Physical Chemistry Quantum theory Stereoselectivity Theoretical and Computational Chemistry |
title | Diastereoselective green synthesis of pyrrolo[1,2-a]quinolines via [3+2] cycloaddition reaction: insights from molecular electron density theory |
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