TY - JOUR
T1 - Molecular Disorder in (-)-Encecanescin
AU - Reyes-Trejo, Benito
AU - Guerra-Ramírez, Diana
AU - Zuleta-Prada, Holber
AU - Santillán, Rosa
AU - Sánchez-Mendoza, María Elena
AU - Arrieta, Jesús
AU - Reyes, Lino
PY - 2014/4
Y1 - 2014/4
N2 - (-)-Encecanescin (1) has been isolated from the leaves of Eupatorium aschembornianum. Two conformers are present in the crystal structure as a result of molecular disorder. The structure of 1 was established by 1H- and 13C-NMR spectroscopy in CDCl3 solution using 2D NMR techniques (gHSQC, gHMBC and NOESY). A Monte Carlo random search using molecular mechanics followed by the geometry optimization of each minimum energy structure using density functional theory (DFT) calculations at the B3LYP/6-31Glevel and a Boltzmann analysis of the total energies generated accurate molecular models describing the conformational behavior of 1. The three most stable conformers 2-4 of compound 1 were reoptimized at the B3LYP/6-311++G(d,p) level of theory using CHCl3 as a solvent. Correlations between the experimental 1H- and 13C-NMR chemical shifts (dexp) have been found, and the GIAO/B3LYP/6-311++G(d,p) calculated magnetic isotropic shielding tensors (scalc) for conformers 2 and 3, dexp = a + b scalc, are reported. A good linear relationship between the experimental and calculated NMR data has been obtained for protons and carbon atoms.
AB - (-)-Encecanescin (1) has been isolated from the leaves of Eupatorium aschembornianum. Two conformers are present in the crystal structure as a result of molecular disorder. The structure of 1 was established by 1H- and 13C-NMR spectroscopy in CDCl3 solution using 2D NMR techniques (gHSQC, gHMBC and NOESY). A Monte Carlo random search using molecular mechanics followed by the geometry optimization of each minimum energy structure using density functional theory (DFT) calculations at the B3LYP/6-31Glevel and a Boltzmann analysis of the total energies generated accurate molecular models describing the conformational behavior of 1. The three most stable conformers 2-4 of compound 1 were reoptimized at the B3LYP/6-311++G(d,p) level of theory using CHCl3 as a solvent. Correlations between the experimental 1H- and 13C-NMR chemical shifts (dexp) have been found, and the GIAO/B3LYP/6-311++G(d,p) calculated magnetic isotropic shielding tensors (scalc) for conformers 2 and 3, dexp = a + b scalc, are reported. A good linear relationship between the experimental and calculated NMR data has been obtained for protons and carbon atoms.
KW - DFT calculations
KW - Encecanescin
KW - FTIR and NMR spectra
KW - X-ray diffraction
UR - http://www.scopus.com/inward/record.url?scp=84899530287&partnerID=8YFLogxK
U2 - 10.3390/molecules19044695
DO - 10.3390/molecules19044695
M3 - Artículo
SN - 1420-3049
VL - 19
SP - 4695
EP - 4707
JO - Molecules
JF - Molecules
IS - 4
ER -