Dynamic NMR Analysis of Conformational Isomerism in a Diterpenoid Carboxamide
Autor: | Paul D. Woodgate, Richard C. Cambie, Ralph J. Stevenson, Peter S. Rutledge, Michael J. Taylor |
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Rok vydání: | 1996 |
Předmět: | |
Zdroj: | Magnetic Resonance in Chemistry. 34:360-364 |
ISSN: | 1097-458X 0749-1581 |
DOI: | 10.1002/(sici)1097-458x(199605)34:5<360::aid-omr887>3.0.co;2-4 |
Popis: | Conformational changes in N,N-diethyl-14-hydroxy-12,19-dimethoxypodocarpa-8,11,13-triene-13-carboxamide were studied by variable-temperature 1H and 13C NMR over the range 228–328 K using three hydrogen and six carbon indicator sites. The parameters ΔH≠ = 48.7±2.0 kJ mol−1, ΔS≠ = −23±7 J K mol−1 and ΔG298≠ = 55.6±4.3 kJ mol−1 were obtained, which were attributed to restricted rotation of the C-CONEt2 bond. Restricted C—N rotation was also detected for which the free energy of activation at 250 K was ca. 53 kJ mol−1. Hydrogen bonding of the carboxamide to the adjacent hydroxy group can account for the low value of the C—N activation energy. |
Databáze: | OpenAIRE |
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