Journal of the Brazilian Chemical Society | |
Experimental and NMR theoretical methodology applied to geometric analysis of the bioactive clerodane trans-dehydrocrotonin | |
Breno Almeida Soares2  Caio Lima Firme2  Maria Aparecida Medeiros Maciel2  Carlos R. Kaiser1  Eduardo Schilling1  Adailton J. Bortoluzzi1  | |
[1] ,Universidade Federal do Rio Grande do Norte Instituto de Química Natal RN ,Brazil | |
关键词: Croton cajucara; trans-dehydrocrotonin; NMR; DFT calculations; QTAIM; X-ray crystallography; | |
DOI : 10.5935/0103-5053.20140010 | |
来源: SciELO | |
【 摘 要 】
trans-Dehydrocrotonin (t-DCTN) a bioactive 19-nor-diterpenoid clerodane type isolated from Croton cajucara Benth, is one of the most investigated clerodane in the current literature. In this work, a new approach joining X-ray diffraction data, nuclear magnetic resonance (NMR) data and theoretical calculations was applied to the thorough characterization of t-DCTN. For that, the geometry of t-DCTN was reevaluated by X-ray diffraction as well as ¹H and 13C NMR data, whose geometrical parameters where compared to those obtained from B3LYP/6-311G++(d,p) level of theory. From the evaluation of both calculated and experimental values of ¹H and 13C NMR chemical shifts and spin-spin coupling constants, it was found very good correlations between theoretical and experimental magnetic properties of t-DCTN. Additionally, the delocalization indexes between hydrogen atoms correlated accurately with theoretical and experimental spin-spin coupling constants. An additional topological analysis from quantum theory of atoms in molecules (QTAIM) showed intramolecular interactions for t-DCTN.
【 授权许可】
CC BY
All the contents of this journal, except where otherwise noted, is licensed under a Creative Commons Attribution License
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