## 2-dehydro-propene cation, CH2=C(+)CH3+ (see note)

 H7 H3 \ / C6 - C1 - C2 / | \ H8 H5 H4
The ion charge is 1.

## Atomic Charges and Dipole Moment

C1 charge= 0.530
C2 charge=-0.468
H3 charge= 0.277
H4 charge= 0.258
H5 charge= 0.257
C6 charge=-0.669
H7 charge= 0.401
H8 charge= 0.412
with a dipole moment of 2.49997 Debye

## Bond Lengths:

between C1 and C2: distance=1.402 ang___ between C1 and H4: distance=2.105 ang___
between C1 and H5: distance=2.107 ang___ between C1 and C6: distance=1.275 ang___
between C2 and H3: distance=1.128 ang___ between C2 and H4: distance=1.108 ang___
between C2 and H5: distance=1.108 ang___ between C2 and C6: distance=2.677 ang___
between C6 and H7: distance=1.107 ang___ between C6 and H8: distance=1.108 ang___

## Bond Angles:

for H3-C2-C1: angle=103.3 deg___ for H4-C2-C1: angle=113.4 deg___
for H5-C2-C1: angle=113.6 deg___ for C6-C1-C2: angle=178.7 deg___
for H7-C6-C1: angle=122.8 deg___ for H8-C1-C2: angle=154.0 deg___

## Bond Orders (Mulliken):

between C1 and C2: order=0.624___ between C1 and H4: order=-0.061___
between C1 and H5: order=-0.061___ between C1 and C6: order=1.868___
between C2 and H3: order=0.903___ between C2 and H4: order=0.974___
between C2 and H5: order=0.974___ between C2 and C6: order=0.122___
between C6 and H7: order=0.961___ between C6 and H8: order=0.971___

## Best Lewis Structure

The Lewis structure that is closest to your structure is determined. The hybridization of the atoms in this idealized Lewis structure is given in the table below. Please note that your structure can't be well described by a single Lewis structure, because of extensive delocalization.

### Hybridization in the Best Lewis Structure

1. A bonding orbital for C1-C2 with 1.9938 electrons
__has 50.65% C 1 character in a sp1.03 hybrid
__has 49.35% C 2 character in a sp2.44 hybrid

2. A bonding orbital for C1-C6 with 1.9942 electrons
__has 50.01% C 1 character in a sp0.97 hybrid
__has 49.99% C 6 character in a sp1.58 hybrid

3. A bonding orbital for C1-C6 with 1.9765 electrons
__has 54.84% C 1 character in a p-pi orbital ( 99.86% p 0.14% d)
__has 45.16% C 6 character in a p-pi orbital ( 99.63% p 0.37% d)

4. A bonding orbital for C2-H3 with 1.8927 electrons
__has 65.11% C 2 character in a s0.76 p3 hybrid
__has 34.89% H 3 character in a s orbital

5. A bonding orbital for C2-H4 with 1.9616 electrons
__has 64.55% C 2 character in a sp2.93 hybrid
__has 35.45% H 4 character in a s orbital

6. A bonding orbital for C2-H5 with 1.9625 electrons
__has 64.54% C 2 character in a sp2.91 hybrid
__has 35.46% H 5 character in a s orbital

7. A bonding orbital for C6-H7 with 1.9362 electrons
__has 65.56% C 6 character in a sp2.22 hybrid
__has 34.44% H 7 character in a s orbital

8. A bonding orbital for C6-H8 with 1.9311 electrons
__has 65.54% C 6 character in a sp2.28 hybrid
__has 34.46% H 8 character in a s orbital

12. A lone pair orbital for C1 with 0.2516 electrons

-With core pairs on: C 1 C 2 C 6 -

#### Donor Acceptor Interactions in the Best Lewis Structure

The localized orbitals in your best Lewis structure can interact strongly. A filled bonding or lone pair orbital can act as a donor and an empty or filled bonding, antibonding, or lone pair orbital can act as an acceptor. These interactions can strengthen and weaken bonds. For example, a lone pair donor->antibonding acceptor orbital interaction will weaken the bond associated with the antibonding orbital. Conversly, an interaction with a bonding pair as the acceptor will strengthen the bond. Strong electron delocalization in your best Lewis structure will also show up as donor-acceptor interactions.
Interactions greater than 20 kJ/mol for bonding and lone pair orbitals are listed below.

The interaction of the second bonding donor orbital, 3, for C1-C6 with the antibonding acceptor orbital, 99, for C2-H4 is 24.1 kJ/mol.

The interaction of the second bonding donor orbital, 3, for C1-C6 with the antibonding acceptor orbital, 100, for C2-H5 is 24.4 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-H3 with the lone pair acceptor orbital, 12, for C1 is 169. kJ/mol.

The interaction of bonding donor orbital, 5, for C2-H4 with the lone pair acceptor orbital, 12, for C1 is 20.4 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-H4 with the second antibonding acceptor orbital, 97, for C1-C6 is 29.0 kJ/mol.

The interaction of bonding donor orbital, 6, for C2-H5 with the second antibonding acceptor orbital, 97, for C1-C6 is 29.2 kJ/mol.

The interaction of bonding donor orbital, 7, for C6-H7 with the lone pair acceptor orbital, 12, for C1 is 91.0 kJ/mol.

The interaction of bonding donor orbital, 7, for C6-H7 with the antibonding acceptor orbital, 95, for C1-C2 is 24.6 kJ/mol.

The interaction of bonding donor orbital, 8, for C6-H8 with the lone pair acceptor orbital, 12, for C1 is 107. kJ/mol.

The interaction of bonding donor orbital, 8, for C6-H8 with the antibonding acceptor orbital, 95, for C1-C2 is 22.7 kJ/mol.

The interaction of lone pair donor orbital, 12, for C1 with the antibonding acceptor orbital, 101, for C6-H7 is 21.0 kJ/mol.

The interaction of lone pair donor orbital, 12, for C1 with the antibonding acceptor orbital, 102, for C6-H8 is 21.0 kJ/mol.

## Molecular Orbital Energies

The orbital energies are given in eV, where 1 eV=96.49 kJ/mol. Orbitals with very low energy are core 1s orbitals. More antibonding orbitals than you might expect are sometimes listed, because d orbitals are always included for heavy atoms and p orbitals are included for H atoms. Up spins are shown with a ^ and down spins are shown as v.

15 ----- -3.174

14 ----- -3.955

13 ----- -7.485

12 ----- -10.59

11 -^-v- -13.80

10 -^-v- -16.63

9 -^-v- -17.43

8 -^-v- -18.03

7 -^-v- -18.16

6 -^-v- -19.74

5 -^-v- -24.87

4 -^-v- -27.07

3 -^-v- -273.5 2 -^-v- -273.5

1 -^-v- -275.7

## Total Electronic Energy

The total electronic energy is a very large number, so by convention the units are given in atomic units, that is Hartrees (H). One Hartree is 2625.5 kJ/mol. The energy reference is for totally dissociated atoms. In other words, the reference state is a gas consisting of nuclei and electrons all at infinite distance from each other. The electronic energy includes all electric interactions and the kinetic energy of the electrons. This energy does not include translation, rotation, or vibration of the the molecule.

Total electronic energy = -116.9855210894 Hartrees