关键词:
chalcone
2 '-hydroxy-3,4,5-trimethoxy-chalcone
GIAO-NMR
scaling factor
NMR spectroscopy
摘要:
In this paper we investigated the ability of the GIAO-mPW1PW91/6-31G(d)//mPW1PW91/6-31G(d) level of theory to predict the C-13 nuclear magnetic resonance (NMR) chemical shifts of the 2'-hydroxy3,4,5-trimethoxy-chalcone molecule. Two different approaches were used. First: the absolute shieldings sigma for all carbon atoms in each geometrically optimized conformers of the 2'-hydroxy3,4,5-trimethoxy-chalcone molecule were calculated at the GIAO-mPW1PW91/6-31G(d)//mPW1PW91/6-31G(d) level of theory. This approach is further used to generate weighted average values for each atom considering the previously obtained conformational distribution. Second: only the s for the lowest energetic conformer will be taken to account. The robustness of the method was evaluated for two other chalcones: (E)-1-(4-hydroxy-3-methoxyphenyl)-3-(3,5-di-tert-butyl-4-hydroxyphenyl) prop-2-en-1-one and (E)-1-(4-aminophenyl)-3-(3,4-dimethoxyphenyl) prop-2-en1-one, corroborating the ability of the method in chemical shift prevision. Although, both approaches were able to reproduce the chemical shifts of the 2'-hydroxy-3,4,5-trimethoxy-chalcone, significant differences in the calculated values for C-4 and methoxy carbons were observed. The best results were obtained using the second approach (II).