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Unusual two‐bond 13 C, 13 C coupling constants in sulphones
Author(s) -
Rücker Christoph,
Fritz Hans
Publication year - 1988
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.1260261213
Subject(s) - chemistry , coupling (piping) , coupling constant , branching (polymer chemistry) , carbon 13 , crystallography , stereochemistry , computational chemistry , physics , nuclear physics , organic chemistry , mechanical engineering , particle physics , engineering
A measurable coupling between carbon atoms through the SO 2 group is observed in a series of structurally diverse sulphones. In open‐chain (single coupling path) sulphones this 2 J coupling ranges from 5.5 to 27.2 Hz, while in cyclic (multiple coupling path) sulphones values ranging from 4.3 to 21.6 Hz are observed. Sulphides and sulphoxides do not exhibit a corresponding coupling of comparable magnitude. A positive sign for this coupling is derived from the data of cyclic sulphones. Whereas substituents and branching at the coupling termini exert minor influences on the coupling, the most important factor determining the magnitude of the 2 J (CSC) coupling is the hybridization of the coupling carbon atoms. A linear relationship between the 2 J value and the s character product of the CS bond forming C orbitals is estalished.