Synthesis of E-Isomer of α-Hydrazone Phosphonates via Nucleophilic Addition of Trialkyl Phosphite to Nitrile Imines (NIs) and DFT Calculations

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dc.authoridÇakır, Sıdıka Polat / 0000-0003-3639-2539
dc.authoridAltınışık, Sinem / 0000-0003-0238-0169
dc.contributor.authorÇakır, Sıdıka Polat
dc.contributor.authorAltınışık, Sinem
dc.date.accessioned2025-01-27T19:28:45Z
dc.date.available2025-01-27T19:28:45Z
dc.date.issued2024
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractNitrile imines (NIs) belong to the nitrilium betaine family of 1,3-dipoles. Due to their high reactivity, NI compounds cannot be isolated and must be generated in situ before undergoing the desired transformation. NI derivatives were prepared by the utilization of N-phenyl hydrazine chloride precursors in the presence of a base. The title compounds α-hydrazone phosphonates have the potential to be biologically active and may serve as a precursor compound for other biologically active substances like amino phosphonic acids. Shortly, they are highly significant compounds in medicinal and synthetic chemistry. The derivatives of α-hydrazone phosphonate are synthesized by the nucleophilic addition of trialkyl phosphite to in situ generated NI derivatives and obtained in 44-95% isolated chemical yields. It is worth noting that only the E-isomer of the α-hydrazone phosphonates was obtained. Structural analyses of the α-hydrazone phosphonates were conducted by using proton and carbon NMR analysis along with FTIR. The researchers also performed DFT calculations including structural parameters (bond length, bond angle, and dihedral angle), HOMO and LUMO energy levels, and the zero-point vibrational energy (ZPE) for both E and Z geometric isomers of unsubstituted phenyl α-hydrazone phosphonate.
dc.identifier.doi10.28979/jarnas.1418948
dc.identifier.endpage425
dc.identifier.issn2757-5195
dc.identifier.issue2
dc.identifier.startpage415
dc.identifier.trdizinid1247308
dc.identifier.urihttps://doi.org/10.28979/jarnas.1418948
dc.identifier.urihttps://search.trdizin.gov.tr/tr/yayin/detay/1247308
dc.identifier.urihttps://hdl.handle.net/20.500.12428/15878
dc.identifier.volume10
dc.indekslendigikaynakTR-Dizin
dc.language.isoen
dc.publisherÇanakkale Onsekiz Mart University
dc.relation.ispartofJournal of advanced research in natural and applied sciences (Online)
dc.relation.publicationcategoryMakale - Ulusal Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_TRD_20250125
dc.subjectNitrile imines
dc.subjectnucleophilic addition
dc.subjecttrialkyl phosphite
dc.subjectα-hydrazone phosphonates
dc.subject1,3-dipole
dc.titleSynthesis of E-Isomer of α-Hydrazone Phosphonates via Nucleophilic Addition of Trialkyl Phosphite to Nitrile Imines (NIs) and DFT Calculations
dc.typeArticle

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