Chemistry Reference
In-Depth Information
Fig. 11.11
The graphical plot for the bondonic features of molecules in Table
11.17
for their
delocalization energies of Table
11.16
Table 11.18
Electronic densities (
ρ
r
) calculated by HMO method for atoms of some coupling
components of sulfanilic acid and sulfanilamide diazonium salts
No.
ρ
1
ρ
2
ρ
3
ρ
4
ρ
5
ρ
6
ρ
7
ρ
8
ρ
9
ρ
10
ρ
11
XIII,
XIV
0.9547 1.0400 0.9980
1
.
0292
0.9980 1.0400 1.9400 -
-
-
-
XV
1.9306 0.9035 1.0572 0.9523
1
.
0288
0.9574
1
.
0417
0.6394 1.8953 1.5939 -
XVI
0.9538
1
.
0484
0.9977
1
.
0367
0.9977
1
.
0484
1.9172 -
-
-
-
XVII
0.9521
1
.
0989
0.9521
1
.
0835
0.9953
1
.
0835
1.9173 1.9173 -
-
-
VI
0.9442
1
.
0561
0.9958
1
.
0407
1.0071 0.9983 1.0095 0.9934 1.0210 0.9993 1.9346
XVIII
1
.
0566
0.9530 1.0259 0.9957 0.9983 1.0097 1.0000 1.0096 0.9984 1.0138 1.9399
XIX
0.9418
1
.
0685
0.9952
1
.
0514
1.0092 0.9980 1.0127 0.9923 1.0248 0.9993 1.9076
XX
1
.
0695
0.9516 1.0305 0.9951 0.9980 1.0124 1.0000 1.0122 0.9982 1.0177 1.9154
(
XIX
)
>
(
VI
)
(11.67c)
(
XVIII
)
>
(
VI
)
(11.67d)
(
XX
)
>
(
XIX
)
(11.67e)
(
XX
)
>
(
XVIII
)
(11.67f)
according to their experimental behavior.
The diazonium cations (XI), (XII) perform electrophilic attacks to the following
atoms: C(4) of (XIII), (XIV), (XVI), (XVII), (VI), (XIX), C(5) of (XV) and C(1)
of (XVIII), (XX) coupling components. It should be mentioned that the (
−
SO
3
H)
