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Conformational analysis of 14‐hydroxymodhephene by NMR, x‐ray diffraction and molecular modeling studies
Author(s) -
ReyesTrejo Benito,
MoralesRíos Martha S.,
AlvarezCisneros E. Celina,
JosephNathan Pedro
Publication year - 2003
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1294
Subject(s) - chemistry , conformational isomerism , cyclopentane , propellane , nuclear magnetic resonance spectroscopy , crystallography , molecule , molecular model , x ray crystallography , stereochemistry , diffraction , bicyclic molecule , organic chemistry , physics , optics
The conformational state of the [3.3.3]propellane framework for 14‐hydroxymodhephene was determined by extensive application of one‐ and two‐dimensional 1 H and 13 C NMR spectroscopy combined with x‐ray diffraction studies of a synthesized derivative, spectral simulation and molecular modeling. The conformational rigidity of the molecule in solution, established at room temperature, revealed the existence of envelope conformers for both cyclopentane fragments, with C‐7 puckered endo and C‐10 exo with respect to the mean plane containing the B and C rings. Copyright © 2003 John Wiley & Sons, Ltd.