Conformational
energies. The solvent in parentheses in cases where large solvent dependence is
observed.
|
Group |
A-value
(kcal/mol) |
t (¼C) |
|
D |
0.006 |
25 |
|
T |
0.011 |
-88 |
|
F |
0.25-0.42 |
-86 to
-93, -25 |
|
Cl |
0.53-0.64 |
-80 to
-93, 25-27 |
|
Br |
0.48-0.67 |
-81, 25-27 |
|
I |
0.47-0.61 |
-78, -93,
25 |
|
OH(C6H12) |
0.60 |
25 |
|
OH(CS2) |
1.04 |
-83 |
|
OH(CH3CHOHCH3) |
0.95 |
25 |
|
OCD3,
OCH3 |
0.55,
0.58, 0.63, 0.75 |
-82, -93 |
|
OC(CH3)3 |
0.75 |
36 |
|
OC6H5 |
0.65 |
-93 |
|
OC6H4NO2-p |
0.62 |
-93 |
|
OC6H4Cl-p |
0.65 |
-93 |
|
OC6H4OCH3-p |
0.70 |
-93 |
|
OCHO |
0.27,
0.60 |
25, -80 to
-93 |
|
OCOCH3 |
0.68,
0.71, 0.79, 0.87 |
25, -90 ±
3 |
|
OCOCF3 |
0.68,
0.56 |
25, -88
to -93 |
|
OCOC6H5 |
0.5 |
-92 ± 1 |
|
OCONHC6H5 |
0.77 |
-91 |
|
OSO2C6H5CH3-p |
0.50 |
-80 to
-83 |
|
OSO2CH3 |
0.56 |
-88 |
|
ONO2 |
0.59,
0.62 |
25, -101 |
|
OSi(CH3)3 |
0.74 |
-103 |
|
SH |
1.21 |
-80 |
|
SCD3,
SCH3 |
1.04 |
-79 to
-100 |
|
SC6H5 |
1.10-1.24 |
-80 |
|
SOCH3 |
1.20 |
-90 to
-100 |
|
SO2CH3 |
2.50 |
-90 to
-100 |
|
SCN |
1.23 |
-79 |
|
SeC6H5 |
1.0-1.2 |
-50 |
|
SeOC6H5 |
1.25 |
-60 |
|
TeC6H5 |
0.9 |
-30 |
|
NH2
(tol-d8;
CFCl3) |
1.23,
1.47 |
-80 to
-100 |
|
NH2
(CH3OCH2CH2OH/H2O) |
1.7 |
20 |
|
NH3+ |
1.7-2.0 |
20-25 |
|
NHCH3
(CFCl3-CDCl3) |
1.29 |
-80 |
|
N(CH3)2
(CFCl3-CDCl3) |
1.53 |
-90 |
|
N(CH3)2
(CH3OCH2CH2OH/H2O) |
2.1 |
20 |
|
NH(CH3)2+ |
2.4 |
20 |
|
NHCOC6H5 |
1.6 |
-90 |
|
NC |
0.20 |
-80 to
-93 |
|
NCO |
0.44,
0.51 |
-70 to
-80 |
|
N3 |
0.45-0.62 |
-183, -93 |
|
NCS |
0.25 |
-79 to
-93 |
|
N=CHCH(CH3)2 |
0.75 |
32 |
|
N=C=NC6H11 |
0.96 |
-80 |
|
NO2 |
1.1 |
-80 to
-90, 25 |
|
PH2 |
1.6 |
-90, 27 |
|
P(CH3)2 |
1.5, 1.6 |
-90, 27 |
|
P(C6H5)2 |
1.8 |
37 |
|
PCl2 |
1.9, 2.0 |
-90, 27 |
|
P(OCH3)2 |
1.9; 1.5 |
-90, 27 |
|
O=P(C6H5)2 |
2.46 |
-80 |
|
S=P(C6H5)2 |
3.13 |
-102 |
|
CHO |
0.56-0.73,
0.8 |
25 |
|
COCH3 |
1.02,
1.21, 1.52 |
-100, 25 |
|
CO2H |
1.4 |
25 |
|
CO2- |
2.0 |
25 |
|
CO2CH3 |
1.2-1.3 |
25, -78 |
|
CO2Et |
1.1-1.2 |
25 |
|
COF |
1.4-1.7 |
25 |
|
COCl |
1.3 |
25 |
|
CN |
0.2 |
-79 to
-95 |
|
CCH |
0.41-0.52 |
-91 |
|
CH=CH2 |
1.49,
1.68 |
-100 |
|
CH=C=CH2 |
1.53 |
-80 |
|
CH3 |
1.74 |
27 |
|
CD3* |
0.0115 |
25-27 |
|
CH2CH3 |
1.79 |
27 |
|
CH(CH3)2 |
2.21 |
27 |
|
C(CH3)3 |
4.7; 4.9 |
-120 |
|
CH2Br |
1.79 |
27 |
|
CH2OH |
1.76 |
27 |
|
CH2COH |
1.72 |
27 |
|
CH2CN |
1.77 |
27 |
|
CH2Si(CH3)3 |
1.65 |
27 |
|
CH2Sn(CH3)3 |
1.79 |
27 |
|
CH2Pb(CH3)3 |
1.81 |
27 |
|
CH2HgOAc |
2.05 |
27 |
|
CF3 |
2.4-2.5 |
27 |
|
C6H5 |
2.8 |
-100, 700 |
|
CH2C6H5 |
1.68 |
-71 |
|
C6H11 |
2.2 |
36 |
|
SiH3 |
1.45;
1.52 |
-85, 75 |
|
Si(CH3)3 |
2.5 |
33 |
|
SiCl3 |
0.61 |
-80 |
|
Ge(CH3)3 |
2.1 |
-70 |
|
Ge(C6H5)3 |
2.90 |
Not given |
|
Sn(CH3)3 |
1.0 |
-69 to
-90 |
|
Sn(i-Pr)3 |
1.10 |
Not given |
|
Sn(CH3)2C6H5 |
1.08 |
Not given |
|
SnCH3(C6H5)2 |
1.20 |
Not given |
|
Sn(C6H5)3 |
1.44 |
Not given |
|
Pb(CH3)3 |
0.67 |
-69 |
|
HgOAc |
0, -0.3 |
-79, -90 |
|
HgCl |
-0.25 |
-90 |
|
HgBr |
0 |
-79 |
|
MgBr(Et2O) |
0.78 |
-75 |
|
MgC6H11(Et2O) |
0.53 |
-82 |
*Difference
between CH3 and CD3; CD3 has lesser equatorial
preference than CH3.
Eliel, E.
L., Wilen, S. H. & Mander, L. N. Stereochemistry of Organic Compounds,
New York: Wiley & Sonds, 1994, p. 696-697.