Jr. Nanney et Cal. Mahaffy, THE USE OF THE F-19 NMR-SPECTRA OF FLUOROPYRIDINES AND RELATED-COMPOUNDS TO VERIFY THE STATISTICAL SUBSTITUENT CHEMICAL-SHIFT VALUES OF FLUOROARENES, Journal of fluorine chemistry, 68(2), 1994, pp. 181-200
F-19 NMR data for fluorosubstituted-pyridines, -pyridazines, -pyrimidi
nes, -pyrazines and -1,3,5-triazines has been used to verify previousl
y published statistical substituent chemical shift (SSCS) values for f
luoroarenes. The data also allowed generation of a set of structure fa
ctors for aromatic nitrogen heterocycles which allows the signals for
these compounds to be predicted from the same set of SSCS values as fl
uoroarenes. When these values are used to predict the F-19 NMR signal
positions of the nitrogen heterocycles, they give a correlation coeffi
cient of predicted versus observed values of 0.987 with a standard dev
iation of 4.5 compared with 0.995 and 2.46, respectively, for the fluo
roarenes.