Synthesis of (3,6-dihydro-2H-pyran-2-yl)phosphonate derivatives and investigation of catalyst effect on frontier molecular orbitals using DFT method

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dc.authoridNadeem, Said/0000-0001-5025-9326
dc.authoridOzpinar, Gul/0000-0002-6913-183X
dc.contributor.authorHossain, Md Shakhawoat
dc.contributor.authorCakir, Sidika Polat
dc.contributor.authorOzpinar, Gul Altinbas
dc.contributor.authorNadeem, Said
dc.contributor.authorDemir, Ayhan S.
dc.date.accessioned2025-01-27T20:24:51Z
dc.date.available2025-01-27T20:24:51Z
dc.date.issued2016
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractHetero Diels-Alder (HDA) reactions between 2,3-dimethyl-1,3-butadiene and diethyl ester of aroyl phosphonates catalyzed by AlCl3 to afford (3,6-dihydro-2H-pyran-2-yl) phosphonate derivatives were investigated. Aroyl phosphonates with electron-withdrawing groups generally resulted in better isolated chemical yields. A stoichiometric amount of AlCl3 rather than a catalytic amount was necessary to activate the cycloaddition reaction. The amount of AlCl3 catalyst and its effect on LUMO of ethyl ester benzoyl phosphonate were also investigated by performing density functional theory (DFT) (B97D/6-31+G(d,p)) computations in dichloromethane. An increased loading of AlCl3 induced a considerable decrease in the LUMO energy of ethyl ester of benzoyl phosphonate. The computed Gibbs free activation energy is 17.03kcal/mol in DCM at 0 degrees C using the same computational level.
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK); Middle East Technical University (METU)
dc.description.sponsorshipFinancial support from the Scientific and Technological Research Council of Turkey (TUBITAK) and the Middle East Technical University (METU) are all appreciatively acknowledged.
dc.identifier.doi10.1080/10426507.2016.1166502
dc.identifier.endpage1267
dc.identifier.issn1042-6507
dc.identifier.issn1563-5325
dc.identifier.issue9
dc.identifier.scopus2-s2.0-84978516872
dc.identifier.scopusqualityQ3
dc.identifier.startpage1262
dc.identifier.urihttps://doi.org/10.1080/10426507.2016.1166502
dc.identifier.urihttps://hdl.handle.net/20.500.12428/22366
dc.identifier.volume191
dc.identifier.wosWOS:000382941000014
dc.identifier.wosqualityQ4
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherTaylor & Francis Ltd
dc.relation.ispartofPhosphorus Sulfur and Silicon and The Related Elements
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectAroyl phosphonate
dc.subjectcycloaddition reaction
dc.subject2
dc.subject3-dimethyl 1
dc.subject3-butadiene
dc.subjectB97D
dc.subjectfrontier molecular orbital
dc.titleSynthesis of (3,6-dihydro-2H-pyran-2-yl)phosphonate derivatives and investigation of catalyst effect on frontier molecular orbitals using DFT method
dc.typeArticle

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