Natural Bond Orbital plots for methyl thiirane
NHO on sulfur
+ NHO on carbon
overlap:
to give a
s
bonding NBO :
NOTE THE BENT BOND!
The antibonding,
s
*
NBO of the other C-S bond
overlaps with the
s
bonding orbital to give this:
causing
s - s
*
delocalisation to stabilise the molecule by 46.8 kJ mol
-1
.