Synthesis of E-Isomer of α-Hydrazone Phosphonates via Nucleophilic Addition of Trialkyl Phosphite to Nitrile Imines (NIs) and DFT Calculations
Nitrile 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 precurs...
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Çanakkale Onsekiz Mart University
2024-06-01
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| Series: | Journal of Advanced Research in Natural and Applied Sciences |
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| Online Access: | https://dergipark.org.tr/en/download/article-file/3656773 |
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| author | Sinem Altınışık Sıdıka Polat Çakır |
| author_facet | Sinem Altınışık Sıdıka Polat Çakır |
| author_sort | Sinem Altınışık |
| collection | DOAJ |
| description | Nitrile 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. |
| format | Article |
| id | doaj-art-3648a58e6b504734a0353221cc2195f1 |
| institution | Kabale University |
| issn | 2757-5195 |
| language | English |
| publishDate | 2024-06-01 |
| publisher | Çanakkale Onsekiz Mart University |
| record_format | Article |
| series | Journal of Advanced Research in Natural and Applied Sciences |
| spelling | doaj-art-3648a58e6b504734a0353221cc2195f12025-02-05T18:13:02ZengÇanakkale Onsekiz Mart UniversityJournal of Advanced Research in Natural and Applied Sciences2757-51952024-06-0110241542510.28979/jarnas.1418948453Synthesis of E-Isomer of α-Hydrazone Phosphonates via Nucleophilic Addition of Trialkyl Phosphite to Nitrile Imines (NIs) and DFT CalculationsSinem Altınışık0https://orcid.org/0000-0003-0238-0169Sıdıka Polat Çakır1https://orcid.org/0000-0003-3639-2539ÇANAKKALE ONSEKİZ MART ÜNİVERSİTESİÇANAKKALE ONSEKİZ MART ÜNİVERSİTESİNitrile 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.https://dergipark.org.tr/en/download/article-file/3656773nitrile iminesnucleophilic additiontrialkyl phosphite13-dipoleα-hydrazone phosphonates |
| spellingShingle | Sinem Altınışık Sıdıka Polat Çakır Synthesis of E-Isomer of α-Hydrazone Phosphonates via Nucleophilic Addition of Trialkyl Phosphite to Nitrile Imines (NIs) and DFT Calculations Journal of Advanced Research in Natural and Applied Sciences nitrile imines nucleophilic addition trialkyl phosphite 1 3-dipole α-hydrazone phosphonates |
| title | Synthesis of E-Isomer of α-Hydrazone Phosphonates via Nucleophilic Addition of Trialkyl Phosphite to Nitrile Imines (NIs) and DFT Calculations |
| title_full | Synthesis of E-Isomer of α-Hydrazone Phosphonates via Nucleophilic Addition of Trialkyl Phosphite to Nitrile Imines (NIs) and DFT Calculations |
| title_fullStr | Synthesis of E-Isomer of α-Hydrazone Phosphonates via Nucleophilic Addition of Trialkyl Phosphite to Nitrile Imines (NIs) and DFT Calculations |
| title_full_unstemmed | Synthesis of E-Isomer of α-Hydrazone Phosphonates via Nucleophilic Addition of Trialkyl Phosphite to Nitrile Imines (NIs) and DFT Calculations |
| title_short | Synthesis of E-Isomer of α-Hydrazone Phosphonates via Nucleophilic Addition of Trialkyl Phosphite to Nitrile Imines (NIs) and DFT Calculations |
| title_sort | synthesis of e isomer of α hydrazone phosphonates via nucleophilic addition of trialkyl phosphite to nitrile imines nis and dft calculations |
| topic | nitrile imines nucleophilic addition trialkyl phosphite 1 3-dipole α-hydrazone phosphonates |
| url | https://dergipark.org.tr/en/download/article-file/3656773 |
| work_keys_str_mv | AT sinemaltınısık synthesisofeisomerofahydrazonephosphonatesvianucleophilicadditionoftrialkylphosphitetonitrileiminesnisanddftcalculations AT sıdıkapolatcakır synthesisofeisomerofahydrazonephosphonatesvianucleophilicadditionoftrialkylphosphitetonitrileiminesnisanddftcalculations |