THEORETICAL AND EXPERIMENTAL CHEMICAL SHIFT STUDY OF ALKALOIDS FROM AMARYLLIDACEAE FAMILY: HAEMANTHAMINE AND ALBOMACULINE

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Detalhes
  • Tipo de apresentação: Resumo Comunicação Oral (VERSÃO PÔSTER)
  • Eixo temático: Profissional
  • Palavras chaves: Alkaloids; GIAO; NMR;
  • 1 Universidade Federal do Espírito Santo
  • 2 Instituto Federal de Ciência e Tecnologia do Espírito Santo

THEORETICAL AND EXPERIMENTAL CHEMICAL SHIFT STUDY OF ALKALOIDS FROM AMARYLLIDACEAE FAMILY: HAEMANTHAMINE AND ALBOMACULINE

Rogério Krohling Siqueira

Universidade Federal do Espírito Santo

Resumo

The alkaloids of the Amaryllidaceae family are secondary metabolites known for their biological activities such as antitumor and antimalarial.1 The chemical structure elucidation of these molecules is essential for the analysis of future potential drugs. Thus, the use of spectroscopic techniques, such as Nuclear Magnetic Resonance, whose chemical shift is one of the properties obtained are fundamental to chemistry studies. However, in some cases, this assignment of chemical shift values can be complicated, due to the structural complexity of some molecules, requiring the use of molecular modeling to extract structural and electronic properties.2 Thus in this work theoretical calculations (DFT-GIAO/B3LYP/cc-pVDZ // PBE0/TZ2P) and experimental ¹H NMR chemical shifts for haemantamine (A) and albomaculine (B) alkaloids were carried out, with the effect of the implicit solvent (chloroform and methanol) and on vacuum, figure 1. The greatest deshielding was possible for position 10, due to the anisotropic effect of the aromatic ring (6-7 ppm) for A and B compounds. For A and B compounds, the best values of R (R = 0.9842 and R = 0.9596) were found for the functional B3LYP with the effect of the implicit solvent, table 1. Therefore, the best correspondences of chemical shifts with the experimental data were found for the functional B3LYP.

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