## H2C=CH=CH2-, allyl anion

 H8 H3 \ / C1 = C2 // \ H7 - C5 H4 | H6
The ion charge is -1.

## Atomic Charges and Dipole Moment

C1 charge= 0.524
C2 charge=-1.280
H3 charge= 0.207
H4 charge= 0.305
C5 charge=-1.288
H6 charge= 0.305
H7 charge= 0.212
H8 charge= 0.015
with a dipole moment of 2.42839 Debye

## Bond Lengths:

between C1 and C2: distance=1.406 ang___ between C1 and H4: distance=2.199 ang___
between C1 and C5: distance=1.406 ang___ between C1 and H6: distance=2.198 ang___
between C1 and H8: distance=1.109 ang___ between C2 and H3: distance=1.096 ang___
between C2 and H4: distance=1.098 ang___ between C2 and C5: distance=2.575 ang___
between C5 and H6: distance=1.098 ang___ between C5 and H7: distance=1.096 ang___

## Bond Angles:

for H3-C2-C1: angle=120.7 deg___ for H4-C2-C1: angle=122.3 deg___
for C5-C1-C2: angle=132.5 deg___ for H6-C5-C1: angle=122.2 deg___
for H7-C5-C1: angle=120.7 deg___ for H8-C1-C2: angle=113.7 deg___

## Bond Orders (Mulliken):

between C1 and C2: order=1.322___ between C1 and H4: order=-0.070___
between C1 and C5: order=1.322___ between C1 and H6: order=-0.070___
between C1 and H8: order=0.933___ between C2 and H3: order=1.012___
between C2 and H4: order=1.013___ between C2 and C5: order=0.171___
between C5 and H6: order=1.014___ between C5 and H7: order=1.012___

## 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 1.9914 electrons
__has 51.84% C 1 character in a sp1.58 hybrid
__has 48.16% C 2 character in a sp1.55 hybrid

2. A bonding orbital for C1-C5 with 1.9914 electrons
__has 51.84% C 1 character in a sp1.58 hybrid
__has 48.16% C 5 character in a sp1.55 hybrid

3. A bonding orbital for C1-C5 with 1.9856 electrons
__has 29.28% C 1 character in a p-pi orbital ( 99.85% p 0.15% d)
__has 70.72% C 5 character in a p-pi orbital ( 99.97% p)

4. A bonding orbital for C1-H8 with 1.9718 electrons
__has 56.66% C 1 character in a s0.88 p3 hybrid
__has 43.34% H 8 character in a s orbital

5. A bonding orbital for C2-H3 with 1.9878 electrons
__has 57.62% C 2 character in a sp2.28 hybrid
__has 42.38% H 3 character in a s orbital

6. A bonding orbital for C2-H4 with 1.9877 electrons
__has 57.64% C 2 character in a sp2.27 hybrid
__has 42.36% H 4 character in a s orbital

7. A bonding orbital for C5-H6 with 1.9877 electrons
__has 57.64% C 5 character in a sp2.27 hybrid
__has 42.36% H 6 character in a s orbital

8. A bonding orbital for C5-H7 with 1.9878 electrons
__has 57.62% C 5 character in a sp2.28 hybrid
__has 42.38% H 7 character in a s orbital

12. A lone pair orbital for C2 with 1.5359 electrons
__made from a p-pi orbital ( 99.97% p)

97. A antibonding orbital for C1-C5 with 0.4450 electrons
__has 70.72% C 1 character in a p-pi orbital ( 99.85% p 0.15% d)
__has 29.28% C 5 character in a p-pi orbital ( 99.97% p)

-With core pairs on: C 1 C 2 C 5 -

#### 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 bonding donor orbital, 4, for C1-H8 with the antibonding acceptor orbital, 100, for C2-H4 is 27.7 kJ/mol.

The interaction of bonding donor orbital, 4, for C1-H8 with the antibonding acceptor orbital, 101, for C5-H6 is 27.7 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-H3 with the antibonding acceptor orbital, 96, for C1-C5 is 32.7 kJ/mol.

The interaction of bonding donor orbital, 6, for C2-H4 with the antibonding acceptor orbital, 98, for C1-H8 is 21.0 kJ/mol.

The interaction of bonding donor orbital, 7, for C5-H6 with the antibonding acceptor orbital, 98, for C1-H8 is 21.0 kJ/mol.

The interaction of bonding donor orbital, 8, for C5-H7 with the antibonding acceptor orbital, 95, for C1-C2 is 32.7 kJ/mol.

The interaction of lone pair donor orbital, 12, for C2 with the second antibonding acceptor orbital, 97, for C1-C5 is 792. 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.

16 ----- 7.695
15 ----- 7.106
14 ----- 6.881

13 ----- 5.867

12 -^-v- 2.386

11 -^-v- -1.017

10 -^-v- -2.123

9 -^-v- -2.969

8 -^-v- -4.134

7 -^-v- -5.138

6 -^-v- -7.080

5 -^-v- -9.805

4 -^-v- -12.57

3 -^-v- -259.3 2 -^-v- -259.3

1 -^-v- -260.3

## 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 = -117.3087772349 Hartrees