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The Origin of One‐Bond C–H Coupling Constants in OCH Fragments: Not Primarily n O → ${{\rm \sigma} {{\ast \hfill \atop {\rm CH}\hfill}}}$ Delocalization
Author(s) -
Cuevas Gabriel,
MartínezMayorga Karina,
FernándezAlonso María del Carmen,
JiménezBarbero Jesús,
Perrin Charles L.,
Juaristi Eusebio,
LópezMora Néstor
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200461583
Subject(s) - dihedral angle , chemistry , crystallography , delocalized electron , coupling constant , tetrahydropyran , physics , ring (chemistry) , quantum mechanics , molecule , hydrogen bond , organic chemistry
Conforming couples : Coupling constants 1 J CH and CH bond lengths were calculated for various conformations of tetrahydropyran, ethyl methyl ether, and dimethyl ether. The dependence of 1 J CH on the H‐C‐O‐C dihedral angle does not parallel the n O → ${{{\rm \sigma} {{\ast \hfill \atop {\rm {\rm CH}}\hfill}}}}$ delocalization (see picture). Dipolar interactions that affect electron densities are proposed to be responsible.