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Table 3 Barriers determined by kinetic isomerization experiments in BAEs including thermal decay of photochromism and electrochemical switching
X,Y
Method a
T Min ( C)
T Max ( C)
Substitution
Process
Barrier (kcal/mol)
Solvent
References
b
2,2 0 -di-H 2 N-
E , Z
25
20
80
C 6 H 6
[ 186 ]
c
CHOH
s ! a
12.5
[ 125 ]
d
C ¼ O
t ! a
15
4
37
DMF
[ 174 ]
c
NCH 3
s
!
a
15
[ 125 ]
d
NCH 3
t
!
a
16.4
20
23
DMF
[ 174 ]
c
S
s
!
a
18
0.5
5
80
MCH/2MP
[ 137 ]
S
2-Me-
Racem.
27.3
45
75
p -Xylene
Polarimetry
[ 187 , 188 ]
2,2 0 -di-Me-
S
E , Z
27.4
HPLC
[ 188 ]
2,2 0 -di-Me-
S
Z -Enantiom.
27.4
HPLC
[ 188 ]
CH
¼
CH
s
!
a
36.4
174
DMSO-d 6
NMR
[ 189 ]
CH
¼
CH, CH 2 -CH 2
s
!
a
23.6
40
CDCl 3
NMR
[ 76 ]
CH
¼
CH, C 6 H 4
s
!
a
36.4
186
DMSO-d 6
NMR
[ 76 ]
a Method for concentration and/or rate determination
b Separation by flash chromatography and photometry
c Thermal reversion of the photochromic E form
d Electrochemical experiments
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