Table 3.

Correlation of the specific rates of reaction of several chloro- and chlorothioformate esters and tert-butyl- and 1-adamantyl fluoroformate using the simple and extended forms^a of the Grunwald-Winstein equation (Equation 1 and Equation 2).

Substrate	nb	lc,d	mc	cc	l/m	Re	Ff	Mechanismg
t-BuSCOCl (1)	19	-	0.73 ± 0.03	−0.10 ± 0.05	-	0.988	686	I
	19	0.13 ± 0.09(0.17)	0.80 ± 0.06	−0.03 ± 0.07	0.16	0.989	365	I
	15	-	0.72 ± 0.03	−0.04 ± 0.06	-	0.990	647	I
	15	0.12 ± 0.09(0.22)	0.78 ± 0.06	0.02 ± 0.07	0.15	0.991	341	I
1-AdOCOClh	15	-	0.47 ± 0.03	0.03 ± 0.05	-	0.985	-	I
	11i	0.08 ± 0.20(0.71)	0.59 ± 0.05	0.06 ± 0.08	0.14	0.985	179	I
2-AdOCOClj	19	-	0.47 ± 0.03	−0.11 ± 0.19	-	0.970	-	I
	19	0.03 ± 0.07(0.70)	0.48 ± 0.04	−0.10 ± 0.19	0.06	0.971	130	I
i-PrOCOClk	9	1.35 ± 0.22	0.40 ± 0.05	0.18 ± 0.07	3.38	0.960	35	A–E
	16	0.28 ± 0.04	0.59 ± 0.04	−0.32 ± 0.06	0.47	0.982	176	I
MeOCOCll	19	1.59 ± 0.09	0.58 ± 0.05	0.16 ± 0.07	2.74	0.977	171	A–E
PhOCOClm	49	1.66 ± 0.05	0.56 ± 0.03	0.15 ± 0.07	2.96	0.980	568	A–E
MeSCOCln	12	1.48 ± 0.18	0.44 ±0.06	0.08 ± 0.08	3.36	0.949	40	A–E
	8	0.79 ± 0.06	0.85 ± 0.07	−0.27 ± 0.08	0.92	0.987	95	I
EtSCOClo	19	0.66 ± 0.08	0.93 ± 0.07	−0.16 ± 0.11	0.71	0.961	96	I
i-PrSCOClp	19	0.38 ± 0.11	0.72 ± 0.09	−0.28 ± 0.10	0.53	0.961	97	I
i-BuSCOClq	15	0.42 ± 0.13	0.73 ± 0.09	−0.37 ± 0.13	0.58	0.961	73	I
t-BuOCOFr	17	0.41 ± 0.05	0.65 ± 0.03	0.02 ± 0.04	0.63	0.989	301	I
1-AdOCOFs	16	-	0.70 +0.01	−0.02 ± 0.05	-	0.999	-	I
Cl3CC(CH3)2OCOClt	33	1.42 ± 0.09	0.39 +0.05	0.16 ± 0.08	3.64	0.945	-	A–E

^aWhich form used is clear from the presence or absence of an l value.

^bn is the number of solvents.

^cWith associated standard error.

^dAccompanied by the probabilities that the lN_T term is not statistically significant when value is greater than 0.001.

^eSimple or multiple correlation coefficient.

^fF-test value.

^gIonization (I) or Addition-Elimination (A–E).

^hValues taken from ref. 22, 23, 30, 31.

ⁱSee ref. 23 for the 11 solvents involved.

^jWith omission of the four data points for 100 and 90% EtOH and MeOH.

^kFrom ref. 23.

^lFrom ref. 18.

^mFrom ref. 49.

ⁿFrom ref. 7.

^oFrom ref. 6.

^pFrom ref. 8.

^qFrom ref. 9.

^rFrom ref. 46.

^sFrom ref. 36.

^tFrom ref. 44.