DFT 1H-1H coupling constants in the conformational analysis and stereoisomeric differentiation of 6-heptenyl-2H-pyran-2-ones: configurational reassignment of synargentolide A

• Published in: Magnetic resonance in chemistry Vol. 53; no. 3; pp. 203 - 212
• Main Authors: Juárez-González, Francisco, Suárez-Ortiz, Gloria Alejandra, Fragoso-Serrano, Mabel, Cerda-García-Rojas, Carlos M., Pereda-Miranda, Rogelio
• Format: Journal Article
• Language: English
• Published: England Blackwell Publishing Ltd 01.03.2015; Wiley Subscription Services, Inc
• Subjects: 1H-1H coupling constants; configuration; conformational analysis; density functional calculations; Molecular Conformation; NMR spectroscopy; Proton Magnetic Resonance Spectroscopy; Pyrans - chemistry; Pyrones - chemistry; spectral simulation; Spectrometry, Mass, Electrospray Ionization; Stereoisomerism; synargentolide A; density functional calculations; 1H-1H coupling constants; configuration; conformational analysis; spectral simulation; NMR spectroscopy; synargentolide A

Density functional theory (DFT) 1H–1H NMR coupling constant calculations, including solvation parameters with the polarizable continuum model B3LYP/DGDZVP basis set together with the experimental values measured by spectral simulation, were used to predict the configuration of hydroxylated 6‐hepteny...