s-trans:

S = 0.22

estimated energy/
interaction: 14.9 kcal/mol

s-cis:
8

bisected S = 0.20
7

6 estimated energy/
relative energy (kcal/mol)

interaction: 12.8 kcal/mol

5

3 slightly
twisted
2
s-cis
1

0 s-trans
0 20 40 60 80 100 120 140 160 180
C=C-C=C dihedral angle (degrees)
-0.41 -0.22
-0.25 -0.23

+0.21 +0.23
 -0.24

-0.20
-0.10

-0.40
small

large
 -0.77 +0.16

+0.22 -0.41

HOMO (nitrile oxide, top) + LUMO (nitrile ox., top) +

LUMO (propyne, bottom) HOMO (propyne, bottom)
Br

Mg
2.17 A