## H2C=CH-O-, Vinyl alcohol anion

 H3 O6 \ / C1 = C2 / \ H4 H5
The ion charge is -1.

## Atomic Charges and Dipole Moment

C1 charge=-1.174
C2 charge= 0.556
H3 charge= 0.269
H4 charge= 0.206
H5 charge=-0.096
O6 charge=-0.760
with a dipole moment of 1.44257 Debye

## Bond Lengths:

between C1 and C2: distance=1.396 ang___ between C1 and H3: distance=1.098 ang___
between C1 and H4: distance=1.098 ang___ between C1 and H5: distance=2.117 ang___
between C1 and O6: distance=2.430 ang___ between C2 and H5: distance=1.138 ang___
between C2 and O6: distance=1.286 ang___

## Bond Angles:

for H3-C1-C2: angle=121.3 deg___ for H4-C1-C2: angle=120.0 deg___
for H5-C2-C1: angle=113.0 deg___ for O6-C2-C1: angle=129.9 deg___

## Bond Orders (Mulliken):

between C1 and C2: order=1.507___ between C1 and H3: order=0.980___
between C1 and H4: order=0.980___ between C1 and H5: order=-0.145___
between C1 and O6: order=-0.084___ between C2 and H5: order=1.112___
between C2 and O6: order=1.370___

## 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 1.9959 electrons
__has 49.87% C 1 character in a sp1.61 hybrid
__has 50.13% C 2 character in a sp1.40 hybrid

2. A bonding orbital for C1-C2 with 1.9937 electrons
__has 70.91% C 1 character in a p-pi orbital ( 99.95% p)
__has 29.09% C 2 character in a p-pi orbital ( 99.80% p 0.20% d)

3. A bonding orbital for C1-H3 with 1.9880 electrons
__has 58.06% C 1 character in a sp2.19 hybrid
__has 41.94% H 3 character in a s orbital

4. A bonding orbital for C1-H4 with 1.9888 electrons
__has 57.40% C 1 character in a sp2.27 hybrid
__has 42.60% H 4 character in a s orbital

5. A bonding orbital for C2-H5 with 1.9826 electrons
__has 53.35% C 2 character in a sp2.93 hybrid
__has 46.65% H 5 character in a s orbital

6. A bonding orbital for C2-O6 with 1.9972 electrons
__has 36.40% C 2 character in a sp1.97 hybrid
__has 63.60% O 6 character in a sp1.72 hybrid

10. A lone pair orbital for O6 with 1.9803 electrons

11. A lone pair orbital for O6 with 1.9132 electrons

12. A lone pair orbital for O6 with 1.7163 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)

86. A antibonding orbital for C1-C2 with 0.2743 electrons
__has 29.09% C 1 character in a p-pi orbital ( 99.95% p)
__has 70.91% C 2 character in a p-pi orbital ( 99.80% p 0.20% d)

-With core pairs on: C 1 C 2 O 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 bonding donor orbital, 4, for C1-H4 with the antibonding acceptor orbital, 90, for C2-O6 is 28.2 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-H5 with the antibonding acceptor orbital, 87, for C1-H3 is 26.9 kJ/mol.

The interaction of lone pair donor orbital, 10, for O6 with the antibonding acceptor orbital, 85, for C1-C2 is 20.5 kJ/mol.

The interaction of the second lone pair donor orbital, 11, for O6 with the antibonding acceptor orbital, 85, for C1-C2 is 65.3 kJ/mol.

The interaction of the second lone pair donor orbital, 11, for O6 with the antibonding acceptor orbital, 89, for C2-H5 is 127. kJ/mol.

The interaction of the third lone pair donor orbital, 12, for O6 with the second antibonding acceptor orbital, 86, for C1-C2 is 555. 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 ----- 8.811

15 ----- 7.856

14 ----- 6.983

13 ----- 5.877

12 -^-v- 1.373

11 -^-v- 1.017

10 -^-v- -2.375

9 -^-v- -2.737

8 -^-v- -3.765

7 -^-v- -4.975

6 -^-v- -7.092

5 -^-v- -11.31

4 -^-v- -17.74

3 -^-v- -259.5

2 -^-v- -261.4

1 -^-v- -498.6

## 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 = -153.2935480807 Hartrees