The synthesis and spectroscopic characterization of (+)-demethoxyaspidospermine: Density functional theory calculations of the structural, electronic, and non-linear optic and spectroscopic properties

Serdaroglu G., Uludag N.

JOURNAL OF CHEMICAL RESEARCH, cilt.43, ss.531-541, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 43
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1177/1747519819875859
  • Dergi Adı: JOURNAL OF CHEMICAL RESEARCH
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.531-541
  • Anahtar Kelimeler: (+)-demethoxyaspidospermine, donor-acceptor systems, frontier molecular orbital analysis, Fourier-transform infrared, non-linear optic, nuclear magnetic resonance, CONCISE TOTAL-SYNTHESIS, FT-IR, HOMO-LUMO, ASPIDOSPERMA ALKALOIDS, MOLECULAR-STRUCTURE, KINETIC STABILITY, INDOLE ALKALOIDS, NMR, NBO, NLO
  • Sivas Cumhuriyet Üniversitesi Adresli: Evet

Özet

(+)-Demethoxyaspidospermine was synthesized via the acylation of aspidospermidine with acetic anhydride, and the structure was determined by elemental analysis and Fourier-transform infrared and nuclear magnetic resonance spectroscopic tools and was supported by the simulated spectroscopic studies. Next, the stable geometries obtained by the conformational analysis performed at the B3LYP/6-31G(d, p) level were used for further investigations carried out in B3LYP and M06-2X functionals, and Hartree-Fock (HF) method, employed by the 6-311++G(d, p) basis set. Also, the natural bond orbital analysis revealed that the most contribution to the lowering of the stabilization energy came from n -> pi* and pi -> pi* interactions. Moreover, the non-linear optic analysis has shown that the title compound can be a useful agent in the optoelectronic devices because of the optical properties. Also, the chemical reactivity tendency for nucleophilic or electrophilic attack reactions on the compound was evaluated by frontier molecular orbital analysis, and the reactive sites of the compound was shown by highest molecular orbital and lowest unoccupied orbital amplitudes and molecular electrostatic potential diagrams.