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. Author manuscript; available in PMC: 2014 Oct 31.
Published in final edited form as: Recent Res Dev Org Chem. 2013;13:1–38.

Table 4.

Correlation of the specific rates of solvolysis of alkyl fluoroformates using the extended (Eqn. 4) form of the Grunwald-Winstein equationa,.

Substrate nb lc mc cc l/m Rd
1-AdOCOF 10e 2.78 ± 0.21 1.01 ± 0.06 0.09 ± 0.16 2.78 0.987
16f ~ 0 0.70 ± 0.01 −0.02 ± 0.05 ~ 0 0.999
t-BuOCOF 17 0.41 ± 0.05 0.65 ± 0.03 0.02 ± 0.04 0.63 0.989
2-AdOCOF 17 1.92 ± 0.15 0.84 ± 0.06 −0.02 ± 0.06 2.28 0.968
i-PrOCOF 20 1.59 ± 0.16 0.80 ± 0.06 −0.12 ± 0.05 1.99 0.957
n-OctOCOF 19 1.67 ± 0.07 0.76 ± 0.03 −0.08 ± 0.18 2.20 0.988
n-PrOCOF 16 1.72 ± 0.12 0.91 ± 0.08 −0.05 ± 0.08 1.89 0.970
EtOCOF 17 1.34 ± 0.14 0.77 ± 0.07 −0.06 ± 0.10 1.74 0.942
MeOCOF 14 1.33 ± 0.09 0.73 ± 0.06 −0.08 ± 0.08 1.82 0.972
C6H5CH2OCOF 13 1.43 ± 0.13 0.70 ± 0.05 −0.09 ± 0.17 2.04 0.974
C6H5COFg 41 1.58 ± 0.09 0.82 ± 0.05 −0.09 ± 0.10 1.93 0.953
a

See text for references to the source of the specific rate values and the derived correlation values.

b

Number of solvents.

c

With associated standard error.

d

Multiple correlation coefficient.

e

By addition-elimination pathway.

f

By ionization pathway.

g

Correlation data for benzoyl fluoride from ref. 117.