3.

9 Å

3.9 Å 5.0 Å
 1.6
1.4 C6H6 - X-C6H6
1.2 C6F6 - X-C6H6

relative interaction energy (kcal/mol)

1.0
0.8
0.6
0.4
0.2
0.0
-0.2
-0.4
-0.6
1.4 -0.8
1.2 -1.0
1.0 -1.2
-1.4
0.8
-1.6
0.6
interaction energy (kcal/mol)

-1.8
0.4
0.2 -0.4 -0.2 0.0 0.2 0.4 0.6 0.8
0.0 meta
-0.2
-0.4 X=H
X=CH2OH y = -1.69 m - 0.82
-0.6
-0.8
-1.0
-1.2
-1.4
-1.6
-1.8
-2.0
-0.4 -0.2 0.0 0.2 0.4 0.6 0.8
meta
 1.6
interaction energy (C6H6 or C6F6) - X-H (kcal/mol)

complexes with C6H6 y = 0.68x + 0.01 (r = 0.94)

1.2
complexes with C6F6
0.8

0.4

0.0

-0.4

-0.8

-1.2

-1.6
y = 1.00x - 0.04 (r = 0.92)
-2.0
-2.0 -1.6 -1.2 -0.8 -0.4 0.0 0.4 0.8 1.2 1.6
interaction energy (C6H6 or C6F6) - X-C6H6 (kcal/mol)
 0.0 increasing
-0.5
interaction
strength
interaction energy (kJ/mol)

-1.0

-1.5
dipoles opposed
-2.0

-2.5

-3.0
increasing
-3.5
electron
-4.0 donation
-0.2 0.0 0.2 0.4 0.6 0.8
meta
Li+