X-ray structures and spectroscopic properties of chiral thiosemicarbazides as studied by computational calculations

Demir Kanmazalp S., Başaran E., Karaküçük-Iyidoğan A., Oruç-Emre E. E., DEGE N.

Phosphorus, Sulfur and Silicon and the Related Elements, cilt.192, sa.7, ss.856-865, 2017 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 192 Sayı: 7
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1080/10426507.2017.1289380
  • Dergi Adı: Phosphorus, Sulfur and Silicon and the Related Elements
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.856-865
  • Anahtar Kelimeler: FTIR, Fukui function analysis, NBO, NMR, Thiosemicarbazide
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

In the present work, (+)-(R)-1-[2-(benzenesulfonamido)-3-phenylpropanoyl]-4-[(4-methoxy)phenyl]thiose micarbazide (1a) and (−)-(S)-1-[2-(benzenesulfonamido)-3-phenylpropanoyl]-4-[(4-methoxy)phenyl] thiosemicarbazide (1b) were synthesized starting with D-phenylalanine methyl ester and L-phenylalanine ethyl ester as a source of chirality. The single crystal structures were characterized by XRD, FTIR and 1H and 13C NMR spectroscopy. Density functional theory (DFT) calculations (B3LYP/6-311G(d,p) were carried out to obtain the ground state optimized geometry, the IR and the NMR spectra of the molecule. Electronic properties (HOMO&LUMO) were calculated using the Time Dependant-DFT/B3LYP/6-311G(d,p) method. Furthermore, NBO, MEP, and Fukui function analyses have been used for the quantitative determination of the chemical activities at various sites of the molecule.