Diels-Alder reactions of [alpha]-cyano [alpha],[beta]-unsaturated ketones with 2-methyl-1,3-butadiene: DFT study of mechanism, reactivity and regioselectivity
The mechanism, reactivity and regioselectivity of Diels-Alder cycloaddition reactions of 2-methyl-1,3-butadiene with four dienophiles, (E)-2-benzylidene-3-oxobutanenitrile, (E)-2-(furan-2-ylmethylene)-3-oxopentanenitrile, (E)-2-benzylidene-4,4-dimethyl-3-oxopentanenitrile, and (E)-2-benzoyl-3-(furan...
Saved in:
Published in | Progress in reaction kinetics and mechanism Vol. 40; no. 2 |
---|---|
Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
London
Sage Publications Ltd
01.04.2015
|
Online Access | Get full text |
Cover
Loading…
Abstract | The mechanism, reactivity and regioselectivity of Diels-Alder cycloaddition reactions of 2-methyl-1,3-butadiene with four dienophiles, (E)-2-benzylidene-3-oxobutanenitrile, (E)-2-(furan-2-ylmethylene)-3-oxopentanenitrile, (E)-2-benzylidene-4,4-dimethyl-3-oxopentanenitrile, and (E)-2-benzoyl-3-(furan-2-yl) acrylonitrile, have been studied by means of several theoretical approaches. The regioselectivity of these reactions has been confirmed by their activation energies, the Gazquez-Mendez rule, Houk's rule and global descriptors of the products. All the studied reactions have normal electron demand character and a polar nature. All calculations were done at the DFT-B3LYP/6-31G(d) level of theory. |
---|---|
AbstractList | The mechanism, reactivity and regioselectivity of Diels-Alder cycloaddition reactions of 2-methyl-1,3-butadiene with four dienophiles, (E)-2-benzylidene-3-oxobutanenitrile, (E)-2-(furan-2-ylmethylene)-3-oxopentanenitrile, (E)-2-benzylidene-4,4-dimethyl-3-oxopentanenitrile, and (E)-2-benzoyl-3-(furan-2-yl) acrylonitrile, have been studied by means of several theoretical approaches. The regioselectivity of these reactions has been confirmed by their activation energies, the Gazquez-Mendez rule, Houk's rule and global descriptors of the products. All the studied reactions have normal electron demand character and a polar nature. All calculations were done at the DFT-B3LYP/6-31G(d) level of theory. |
Author | Zahedi, Ehsan Nouri, Arezu Nouri, Azita Jafari, Fateme Joneydi |
Author_xml | – sequence: 1 givenname: Azita surname: Nouri fullname: Nouri, Azita – sequence: 2 givenname: Ehsan surname: Zahedi fullname: Zahedi, Ehsan – sequence: 3 givenname: Fateme surname: Jafari middlename: Joneydi fullname: Jafari, Fateme Joneydi – sequence: 4 givenname: Arezu surname: Nouri fullname: Nouri, Arezu |
BookMark | eNqNjkFOwzAQRS1UJFrgDpbYxmAnrh3YIUrFAbqoVKHKjafExbFLbINyGc5aVwp7NIuZ_-fpz8zQxHkHCGFG7ytW8wfGRS1kzeZrxkuRi5aSCl5eoCnjkhFOxXpynkVNMlddoVkIB0ozKfkU_S4M2ECerYYe96CaaLwL2O_xRtljq95JMyjn_1Sx2UHMZnJBxdSrCBp_QswvBfxjYotL0kFsB0tYUZFdikobcPCEF8sVDjHp4RzdQdMqZ0JXjCe_TRywcjrLD-MDWBjNG3S5VzbA7div0d3ydfXyRo69_0oQ4vbgU-_yasuElFI8zpmo_kedAIhQZXw |
ContentType | Journal Article |
Copyright | Copyright Science Reviews 2000 Ltd 2015 |
Copyright_xml | – notice: Copyright Science Reviews 2000 Ltd 2015 |
DBID | 7SR 7U5 8BQ 8FD 8FE 8FG ABJCF ABUWG AFKRA AZQEC BENPR BGLVJ CCPQU D1I DWQXO EHMNL HCIFZ JG9 KB. L7M PDBOC PIMPY PQEST PQQKQ PQUKI PRINS |
DOI | 10.3184/146867815X14262620270642 |
DatabaseName | Engineered Materials Abstracts Solid State and Superconductivity Abstracts METADEX Technology Research Database ProQuest SciTech Collection ProQuest Technology Collection Materials Science & Engineering Collection ProQuest Central (Alumni) ProQuest Central ProQuest Central Essentials AUTh Library subscriptions: ProQuest Central Technology Collection ProQuest One Community College ProQuest Materials Science Collection ProQuest Central UK & Ireland Database SciTech Premium Collection (Proquest) (PQ_SDU_P3) Materials Research Database Materials Science Database Advanced Technologies Database with Aerospace Materials Science Collection Access via ProQuest (Open Access) ProQuest One Academic Eastern Edition (DO NOT USE) ProQuest One Academic ProQuest One Academic UKI Edition ProQuest Central China |
DatabaseTitle | Publicly Available Content Database Materials Research Database Technology Collection Technology Research Database ProQuest Central Essentials Materials Science Collection ProQuest Central (Alumni Edition) SciTech Premium Collection ProQuest One Community College ProQuest Central China ProQuest Central Engineered Materials Abstracts ProQuest Central Korea Materials Science Database Advanced Technologies Database with Aerospace ProQuest Materials Science Collection ProQuest One Academic Eastern Edition ProQuest Technology Collection ProQuest SciTech Collection METADEX UK & Ireland Database ProQuest One Academic UKI Edition Materials Science & Engineering Collection Solid State and Superconductivity Abstracts ProQuest One Academic |
DatabaseTitleList | Publicly Available Content Database |
Database_xml | – sequence: 1 dbid: 8FG name: ProQuest Technology Collection url: https://search.proquest.com/technologycollection1 sourceTypes: Aggregation Database |
DeliveryMethod | fulltext_linktorsrc |
Discipline | Chemistry |
EISSN | 1471-406X |
ExternalDocumentID | 3672840311 |
GroupedDBID | 123 29P 31X 3V. 54M 7SR 7U5 8BQ 8FD 8FE 8FG AARIX AATBZ ABCQX ABDBF ABJCF ABQXT ABRHV ABUWG ACDXX ACIWK ACROE ACSIQ ACUIR ADOGD AEDFJ AENEX AEWDL AEWHI AFCOW AFKRA AFKRG AFRWT AFUIA AGNHF AIOMO AJUZI ALMA_UNASSIGNED_HOLDINGS ARTOV AZQEC BDDNI BENPR BGLVJ BPHCQ CCPQU CS3 D1I DV7 DWQXO E3Z EBS EHMNL EJD ESX GROUPED_SAGE_PREMIER_JOURNAL_COLLECTION H13 HCIFZ HH5 HHL I-F IAO J8X JCYGO JG9 KB. L7B L7M M4V OK1 P2P PDBOC PIMPY PQEST PQQKQ PQUKI PRINS PROAC ROL SCNPE SFC SFK SFT SGV SPP TUS ZPPRI ZRKOI |
ID | FETCH-proquest_journals_16777695163 |
IEDL.DBID | BENPR |
ISSN | 1468-6783 |
IngestDate | Thu Oct 10 15:56:27 EDT 2024 |
IsDoiOpenAccess | true |
IsOpenAccess | true |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 2 |
Language | English |
LinkModel | DirectLink |
MergedId | FETCHMERGED-proquest_journals_16777695163 |
OpenAccessLink | https://www.proquest.com/docview/1677769516?pq-origsite=%requestingapplication% |
PQID | 1677769516 |
PQPubID | 1586338 |
ParticipantIDs | proquest_journals_1677769516 |
PublicationCentury | 2000 |
PublicationDate | 20150401 |
PublicationDateYYYYMMDD | 2015-04-01 |
PublicationDate_xml | – month: 04 year: 2015 text: 20150401 day: 01 |
PublicationDecade | 2010 |
PublicationPlace | London |
PublicationPlace_xml | – name: London |
PublicationTitle | Progress in reaction kinetics and mechanism |
PublicationYear | 2015 |
Publisher | Sage Publications Ltd |
Publisher_xml | – name: Sage Publications Ltd |
SSID | ssj0026274 |
Score | 4.033573 |
Snippet | The mechanism, reactivity and regioselectivity of Diels-Alder cycloaddition reactions of 2-methyl-1,3-butadiene with four dienophiles,... |
SourceID | proquest |
SourceType | Aggregation Database |
Title | Diels-Alder reactions of [alpha]-cyano [alpha],[beta]-unsaturated ketones with 2-methyl-1,3-butadiene: DFT study of mechanism, reactivity and regioselectivity |
URI | https://www.proquest.com/docview/1677769516 |
Volume | 40 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV1LS8NAEB5se9CL-MRHLQt67NI8N6kXqW1jESxSKhaKlLwWSm2iJj30z_hbndkmehB6zAQ2j11mvp2dbz6AmwCdoikcnUdmGzcojia5L8yYBxhu9MjFGBISwflpKAYv1uPEnhQJt6woqyx9onLUURpSjrylC8dxBOIBcffxyUk1ik5XCwmNCtQM3aJj2tp9f_g8-t1ykbJMyS9Ct2xuanlwHVstsqFJtyc6dWUXlAUgNP7PKatI4x3AfgERWWczp4ewEydHsNstldmO4bs3x4jGOySwzRD0KWpCxlLJpoo6-8bDtZ-k5VVzGsQ5GldJRl08EVxGbBFTE-6MURqWGZx0pNfvXG-aPFjlqgosvmU9b8xU-1kaehkTR3ieLZvFI0l0gvlJxEjbIc2Uno4ynsC11x93B7z8wFmxYLPZ3-81T6Ga4CucAdN8abm20ZaaMCyJYEBSK5vIJepWaGvyHOrbRrrYfvsS9hB92JsymDpU869VfIURPg8aUHG9hwbUOt7oddwoJvUHuDutxQ |
link.rule.ids | 315,786,790,12792,21416,27955,27956,33406,33777,43633,43838 |
linkProvider | ProQuest |
linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV1LT8JAEN4oHvBifMYH6iZ6ZEPLttvixRCwogInTEiIIX3sJgRp1S0H_oy_1Zml1YMJx06T7WM3M9_OzjcfIbcROEUuPJslvAUbFM9SLBRcsgjCjZ34EENiJDgPhqL36jyP3XGRcNNFWWXpE42jTrIYc-QNW3ieJwAPiPuPT4aqUXi6WkhobJMdhwuO69wPHn83XKgrU7KLwCnzdSUPrGKngTYw2e7Yxp7sAnMAiMX_uWQTZ4J9slcARNpez-gB2ZLpIal2Sl22I_LdnUE8Y22U16YA-QwxQdNM0Ykhzr6xeBWmWXlVn0QyB-My1djDE6BlQucSW3BriklY2mSoIr16Z3ads2iZmxoweUe7wYia5rM49EIiQ3imF_XikSg5QcM0oajskGmjpmOMx-QmeBh1eqz8wGmxXPX07-fyE1JJ4RVOCbVC5fhus6Us0XQUQAGFjWwSH4lbsWupM1LbNNL55tvXpNobDfrT_tPw5YLsAg5x1wUxNVLJv5byEmJ9Hl2ZCf0BkMusvw |
openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Diels-Alder+reactions+of+%5Balpha%5D-cyano+%5Balpha%5D%2C%5Bbeta%5D-unsaturated+ketones+with+2-methyl-1%2C3-butadiene%3A+DFT+study+of+mechanism%2C+reactivity+and+regioselectivity&rft.jtitle=Progress+in+reaction+kinetics+and+mechanism&rft.au=Nouri%2C+Azita&rft.au=Zahedi%2C+Ehsan&rft.au=Jafari%2C+Fateme+Joneydi&rft.au=Nouri%2C+Arezu&rft.date=2015-04-01&rft.pub=Sage+Publications+Ltd&rft.issn=1468-6783&rft.eissn=1471-406X&rft.volume=40&rft.issue=2&rft_id=info:doi/10.3184%2F146867815X14262620270642&rft.externalDocID=3672840311 |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1468-6783&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1468-6783&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1468-6783&client=summon |