A molecular electron density theory investigation of the molecular mechanism, regioselectivity, stereoselectivity and chemoselectivity of cycloaddition reaction between acetonitrile N-oxide and 2,5-dimethyl-2H-[1,2,3]diazarsole
The cycloaddition reactions (32CA) of acetonitrile N-oxide and 2,5-dimethyl-2H-[1,2,3]diazarsole 1 have been examined employing the molecular electron density theory through DFT calculations at the B3LYP/6-31G ++(d,p) computational level. Investigation of the relative energies related to the competi...
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| Veröffentlicht in: | Theoretical chemistry accounts 2020-02, Vol.139 (2), Article 37 |
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| creator | Zeroual, Abdellah Ríos-Gutiérrez, Mar El Ghozlani, Mohamed El Idrissi, Mohammed Ouled Aitouna, Anas Salah, Mohammed El Alaoui El Abdallaoui, Habib Domingo, Luis Ramon |
| description | The cycloaddition reactions (32CA) of acetonitrile N-oxide and 2,5-dimethyl-2H-[1,2,3]diazarsole
1
have been examined employing the molecular electron density theory through DFT calculations at the B3LYP/6-31G ++(d,p) computational level. Investigation of the relative energies related to the competitive
ortho
and
meta
reaction paths demonstrates a high chemo-, stereo- and regioselectivity for this 32CA reaction in clear conformity with the experimental results. The topological study of the electron localisation function of the certain points of the IRC associated with the construction of the As–C and C–O single bonds shows a zwitterionic-type structure. The 32CA reaction takes place via a two-stage one-step mechanism initialised with the formation of the As–C single bond. |
| doi_str_mv | 10.1007/s00214-020-2547-6 |
| format | Article |
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1
have been examined employing the molecular electron density theory through DFT calculations at the B3LYP/6-31G ++(d,p) computational level. Investigation of the relative energies related to the competitive
ortho
and
meta
reaction paths demonstrates a high chemo-, stereo- and regioselectivity for this 32CA reaction in clear conformity with the experimental results. The topological study of the electron localisation function of the certain points of the IRC associated with the construction of the As–C and C–O single bonds shows a zwitterionic-type structure. The 32CA reaction takes place via a two-stage one-step mechanism initialised with the formation of the As–C single bond.</description><identifier>ISSN: 1432-881X</identifier><identifier>EISSN: 1432-2234</identifier><identifier>DOI: 10.1007/s00214-020-2547-6</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Acetonitrile ; Atomic/Molecular Structure and Spectra ; Chemistry ; Chemistry and Materials Science ; Cycloaddition ; Electron density ; Inorganic Chemistry ; Organic Chemistry ; Physical Chemistry ; Regioselectivity ; Regular Article ; Stereoselectivity ; Theoretical and Computational Chemistry</subject><ispartof>Theoretical chemistry accounts, 2020-02, Vol.139 (2), Article 37</ispartof><rights>Springer-Verlag GmbH Germany, part of Springer Nature 2020</rights><rights>2020© Springer-Verlag GmbH Germany, part of Springer Nature 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-1ab4cb7bafa562912bfc9c154ff48bbb033e2a27106dcde332ef66b765a7ba0c3</citedby><cites>FETCH-LOGICAL-c316t-1ab4cb7bafa562912bfc9c154ff48bbb033e2a27106dcde332ef66b765a7ba0c3</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/s00214-020-2547-6$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s00214-020-2547-6$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27923,27924,41487,42556,51318</link.rule.ids></links><search><creatorcontrib>Zeroual, Abdellah</creatorcontrib><creatorcontrib>Ríos-Gutiérrez, Mar</creatorcontrib><creatorcontrib>El Ghozlani, Mohamed</creatorcontrib><creatorcontrib>El Idrissi, Mohammed</creatorcontrib><creatorcontrib>Ouled Aitouna, Anas</creatorcontrib><creatorcontrib>Salah, Mohammed</creatorcontrib><creatorcontrib>El Alaoui El Abdallaoui, Habib</creatorcontrib><creatorcontrib>Domingo, Luis Ramon</creatorcontrib><title>A molecular electron density theory investigation of the molecular mechanism, regioselectivity, stereoselectivity and chemoselectivity of cycloaddition reaction between acetonitrile N-oxide and 2,5-dimethyl-2H-[1,2,3]diazarsole</title><title>Theoretical chemistry accounts</title><addtitle>Theor Chem Acc</addtitle><description>The cycloaddition reactions (32CA) of acetonitrile N-oxide and 2,5-dimethyl-2H-[1,2,3]diazarsole
1
have been examined employing the molecular electron density theory through DFT calculations at the B3LYP/6-31G ++(d,p) computational level. Investigation of the relative energies related to the competitive
ortho
and
meta
reaction paths demonstrates a high chemo-, stereo- and regioselectivity for this 32CA reaction in clear conformity with the experimental results. The topological study of the electron localisation function of the certain points of the IRC associated with the construction of the As–C and C–O single bonds shows a zwitterionic-type structure. The 32CA reaction takes place via a two-stage one-step mechanism initialised with the formation of the As–C single bond.</description><subject>Acetonitrile</subject><subject>Atomic/Molecular Structure and Spectra</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Cycloaddition</subject><subject>Electron density</subject><subject>Inorganic Chemistry</subject><subject>Organic Chemistry</subject><subject>Physical Chemistry</subject><subject>Regioselectivity</subject><subject>Regular Article</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>2020</creationdate><recordtype>article</recordtype><recordid>eNp1kV1LHDEYhQdpQav9Ab0L9Hai-ZjJ7FyKtFoQvVEolBLy8c5uZCaxSVYd_27_iNldofbCqxzenPO8IaeqvlByTAnpThIhjDaYMIJZ23RY7FUHtOEMM8abD696saA_96tPKd2RYmdtd1D9PUVTGMGsRxURFJFj8MiCTy7PKK8gxBk5_wApu6XKrlyGYTN_E5vArJR3aapRhKULactxD4VQo5QhwtsRUt4is4Lpv2GBmtmMQVnrtlsiKLMVGvIjgEfKQA7e5ehGQFc4PDkLWxarW2zdBHk1j5hd4F-0ZjX_bZ16VjGVVx5VHwc1Jvj8eh5Wt9-_3Zxd4Mvr8x9np5fYcCoypko3RndaDaoVrKdMD6Y3tG2GoVlorQnnwBTrKBHWWOCcwSCE7kSrSogYflh93XHvY_izLj8m78I6-rJSlhJ62ou-p8VFdy4TQ0oRBnkf3aTiLCmRmy7lrktZupSbLqUoGbbLpOL1S4j_yO-HXgDH8qkC</recordid><startdate>20200201</startdate><enddate>20200201</enddate><creator>Zeroual, Abdellah</creator><creator>Ríos-Gutiérrez, Mar</creator><creator>El Ghozlani, Mohamed</creator><creator>El Idrissi, Mohammed</creator><creator>Ouled Aitouna, Anas</creator><creator>Salah, Mohammed</creator><creator>El Alaoui El Abdallaoui, Habib</creator><creator>Domingo, Luis Ramon</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20200201</creationdate><title>A molecular electron density theory investigation of the molecular mechanism, regioselectivity, stereoselectivity and chemoselectivity of cycloaddition reaction between acetonitrile N-oxide and 2,5-dimethyl-2H-[1,2,3]diazarsole</title><author>Zeroual, Abdellah ; Ríos-Gutiérrez, Mar ; El Ghozlani, Mohamed ; El Idrissi, Mohammed ; Ouled Aitouna, Anas ; Salah, Mohammed ; El Alaoui El Abdallaoui, Habib ; Domingo, Luis Ramon</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-1ab4cb7bafa562912bfc9c154ff48bbb033e2a27106dcde332ef66b765a7ba0c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Acetonitrile</topic><topic>Atomic/Molecular Structure and Spectra</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Cycloaddition</topic><topic>Electron density</topic><topic>Inorganic Chemistry</topic><topic>Organic Chemistry</topic><topic>Physical Chemistry</topic><topic>Regioselectivity</topic><topic>Regular Article</topic><topic>Stereoselectivity</topic><topic>Theoretical and Computational Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zeroual, Abdellah</creatorcontrib><creatorcontrib>Ríos-Gutiérrez, Mar</creatorcontrib><creatorcontrib>El Ghozlani, Mohamed</creatorcontrib><creatorcontrib>El Idrissi, Mohammed</creatorcontrib><creatorcontrib>Ouled Aitouna, Anas</creatorcontrib><creatorcontrib>Salah, Mohammed</creatorcontrib><creatorcontrib>El Alaoui El Abdallaoui, Habib</creatorcontrib><creatorcontrib>Domingo, Luis Ramon</creatorcontrib><collection>CrossRef</collection><jtitle>Theoretical chemistry accounts</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zeroual, Abdellah</au><au>Ríos-Gutiérrez, Mar</au><au>El Ghozlani, Mohamed</au><au>El Idrissi, Mohammed</au><au>Ouled Aitouna, Anas</au><au>Salah, Mohammed</au><au>El Alaoui El Abdallaoui, Habib</au><au>Domingo, Luis Ramon</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A molecular electron density theory investigation of the molecular mechanism, regioselectivity, stereoselectivity and chemoselectivity of cycloaddition reaction between acetonitrile N-oxide and 2,5-dimethyl-2H-[1,2,3]diazarsole</atitle><jtitle>Theoretical chemistry accounts</jtitle><stitle>Theor Chem Acc</stitle><date>2020-02-01</date><risdate>2020</risdate><volume>139</volume><issue>2</issue><artnum>37</artnum><issn>1432-881X</issn><eissn>1432-2234</eissn><abstract>The cycloaddition reactions (32CA) of acetonitrile N-oxide and 2,5-dimethyl-2H-[1,2,3]diazarsole
1
have been examined employing the molecular electron density theory through DFT calculations at the B3LYP/6-31G ++(d,p) computational level. Investigation of the relative energies related to the competitive
ortho
and
meta
reaction paths demonstrates a high chemo-, stereo- and regioselectivity for this 32CA reaction in clear conformity with the experimental results. The topological study of the electron localisation function of the certain points of the IRC associated with the construction of the As–C and C–O single bonds shows a zwitterionic-type structure. The 32CA reaction takes place via a two-stage one-step mechanism initialised with the formation of the As–C single bond.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><doi>10.1007/s00214-020-2547-6</doi></addata></record> |
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| subjects | Acetonitrile Atomic/Molecular Structure and Spectra Chemistry Chemistry and Materials Science Cycloaddition Electron density Inorganic Chemistry Organic Chemistry Physical Chemistry Regioselectivity Regular Article Stereoselectivity Theoretical and Computational Chemistry |
| title | A molecular electron density theory investigation of the molecular mechanism, regioselectivity, stereoselectivity and chemoselectivity of cycloaddition reaction between acetonitrile N-oxide and 2,5-dimethyl-2H-[1,2,3]diazarsole |
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