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Conformational analysis: 3 J HCOC and 3 J HCCC Karplus relationships for methylene 1 H nuclei
Author(s) -
Grimmer Craig D.,
Slabber Cathryn A.
Publication year - 2015
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.4264
Subject(s) - chemistry , methylene , coupling constant , proton , molecule , density functional theory , coupling (piping) , computational chemistry , crystallography , stereochemistry , medicinal chemistry , physics , nuclear physics , organic chemistry , quantum mechanics , mechanical engineering , engineering
NAMFIS ( N MR A nalysis of M olecular F lexibility I n S olution) was applied to 1‐[2‐(benzyloxy)phenyl]ethanone using quantitative 1 H‐ 1 H NOE distances and 3 J proton‐carbon coupling constant (CC) restraints for averaged methylene proton 3 J HCOC and 3 J HCCC pathways H 2 ‐ 3 J ‐X imposed by density functional theory‐generated Karplus relationships. Comparison of the NOE‐only versus the NOE + CC conformational selections illustrates that the experimentally measured average 3 J coupling constants of methylene protons can be used for solution conformational analysis, potentially valuable in the study of small‐molecule drugs and natural products which lack the typically studied H 1 ‐ 3 J ‐X Karplus relationships. Copyright © 2015 John Wiley & Sons, Ltd.