Highly functionalized N-1-(2-pyridinylmethyl)-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones: Synthesis, characterization, crystal structure and DFT studies

Al-thamili, Dhaifallah; Almansour, Abdulrahman; Arumugam, Natarajan; KANSIZ, SEVGİ; Dege, Necmi; Soliman, Saied; Azam, Mohammad; Kumar, Raju

doi:10.1016/j.molstruc.2020.128940

Highly functionalized N-1-(2-pyridinylmethyl)-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones: Synthesis, characterization, crystal structure and DFT studies

Al-thamili D. M., Almansour A. I., Arumugam N., KANSIZ S., Dege N., Soliman S. M., ...Daha Fazla

Journal of Molecular Structure, cilt.1222, 2020 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 1222
Basım Tarihi: 2020
Doi Numarası: 10.1016/j.molstruc.2020.128940
Dergi Adı: Journal of Molecular Structure
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, Compendex, INSPEC
Anahtar Kelimeler: DFT studies, Functionalized αβ-unsaturated ketones, Hirshfeld, X-ray analysis
Samsun Üniversitesi Adresli: Evet

Özet

Highly functionalized N-1-(2-pyridinylmethyl)-3,5-bis[(E)-methoxy/fluorophenylmethylidene]-tetrahydro-4(1H)-pyridinones (5a and 5b) have been synthesized in good yields. The molecular structure of the synthesized compounds was elucidated by NMR spectroscopy and further confirmed by single crystal X-ray crystallographic studies. The Hirshfeld analysis reveals that the molecular packing of 5a is mainly controlled by N…H (4.9%), C…H (30.6%) and H…H (52.4%) contacts whereas the molecules are packed by strong F…H (16.8−16.9 %), N…H (5.4%) and O…H (5.2−5.4%) as well as weak C…C (3.9−4.5%), H…H (39.7−39.9%) and C…H (24.8−25.8%) contacts in 5b. DFT calculations are used in order to predict the electronic properties of studied compounds. The NMR data obtained experimentally correlated well with the calculated findings.