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Spatial substituent effects of various fluorinated groups on the 13 C chemical shifts in cyclohexanes
Author(s) -
Carcenac Yvan,
Diter Patrick,
Wakselman Claude,
Tordeux Marc
Publication year - 2007
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.1950
Subject(s) - cyclohexanes , chemistry , chemical shift , substituent , heteroatom , cyclohexane , ring (chemistry) , stereochemistry , carbon 13 nmr , fluorine , alicyclic compound , group (periodic table) , medicinal chemistry , organic chemistry
The effect of introduction of fluorinated groups (CH 2 F, CHF 2 , CF 3 , C 2 F 5 , OCF 3 , SCF 3 ) on the 13 C NMR chemical shifts in cyclohexanes is examined. The two main effects are caused by location at the α and γ carbon positions. Comparison of the various data allowed the calculation of increments corresponding to the introduction of fluorinated groups at axial or equatorial positions on the cyclohexane ring. The introduction of fluorine atoms in methoxy and thiomethoxy groups has only a slight effect through the heteroatom on the 13 C chemical shifts. Copyright © 2007 John Wiley & Sons, Ltd.