O3 // O1 - C2 / \\ H5 O4
The multiplicity is 2.

## Atomic Charges and Dipole Moment

O1 charge=-0.497
C2 charge= 0.718
O3 charge=-0.290
O4 charge=-0.369
H5 charge= 0.438
with a dipole moment of 2.93787 Debye

## Bond Lengths:

between O1 and C2: distance=1.344 ang___ between O1 and O3: distance=2.262 ang___
between O1 and O4: distance=2.298 ang___ between O1 and H5: distance=0.983 ang___
between C2 and O3: distance=1.268 ang___ between C2 and O4: distance=1.268 ang___
between C2 and H5: distance=1.903 ang___ between O3 and O4: distance=2.161 ang___

## Bond Angles:

for O3-C2-O1: angle=120.0 deg___ for O4-C2-O1: angle=123.1 deg___
for H5-O1-C2: angle=108.7 deg___

## Bond Orders (Mulliken):

between O1 and C2: order=1.207___ between O1 and O3: order=-0.191___
between O1 and O4: order=-0.205___ between O1 and H5: order=0.816___
between C2 and O3: order=1.717___ between C2 and O4: order=1.509___
between C2 and H5: order=0.065___ between O3 and O4: order=0.172___

## 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.

The Lewis structure is built for the up and down electrons, separately. Note that the up and down structures can be very different.

### Hybridization in the Best Lewis Structure

#### Down Electrons

1. A bonding orbital for O1-C2 with 0.9985 electrons
__has 65.98% O 1 character in a sp2.40 hybrid
__has 34.02% C 2 character in a sp2.13 hybrid

2. A bonding orbital for O1-H5 with 0.9926 electrons
__has 75.40% O 1 character in a s0.88 p3 hybrid
__has 24.60% H 5 character in a s orbital

3. A bonding orbital for C2-O3 with 0.9983 electrons
__has 35.52% C 2 character in a sp1.88 hybrid
__has 64.48% O 3 character in a sp2.23 hybrid

4. A bonding orbital for C2-O4 with 0.9989 electrons
__has 34.60% C 2 character in a sp1.98 hybrid
__has 65.40% O 4 character in a sp2.22 hybrid

9. A lone pair orbital for O1 with 0.9882 electrons

10. A lone pair orbital for O1 with 0.9329 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)

11. A lone pair orbital for C2 with 0.2838 electrons
__made from a p-pi orbital ( 99.97% p)

12. A lone pair orbital for O3 with 0.9916 electrons

13. A lone pair orbital for O3 with 0.9673 electrons

14. A lone pair orbital for O3 with 0.8787 electrons
__made from a p-pi orbital ( 99.88% p 0.12% d)

15. A lone pair orbital for O4 with 0.9915 electrons

16. A lone pair orbital for O4 with 0.9702 electrons

17. A lone pair orbital for O4 with 0.8980 electrons
__made from a p-pi orbital ( 99.88% p 0.12% d)

-With core pairs on: O 1 C 2 O 3 O 4 -

#### Up Electrons

1. A bonding orbital for O1-C2 with 0.9974 electrons
__has 66.17% O 1 character in a sp2.45 hybrid
__has 33.83% C 2 character in a sp2.55 hybrid

2. A bonding orbital for O1-H5 with 0.9913 electrons
__has 75.26% O 1 character in a s0.85 p3 hybrid
__has 24.74% H 5 character in a s orbital

3. A bonding orbital for C2-O3 with 0.9766 electrons
__has 40.14% C 2 character in a sp1.75 hybrid
__has 59.86% O 3 character in a sp2.26 hybrid

4. A bonding orbital for C2-O4 with 0.9664 electrons
__has 39.99% C 2 character in a sp1.81 hybrid
__has 60.01% O 4 character in a sp2.25 hybrid

5. A bonding orbital for O3-O4 with 0.8976 electrons
__has 57.18% O 3 character in a p3 hybrid
__has 42.82% O 4 character in a s0.06 p3 hybrid

10. A lone pair orbital for O1 with 0.9858 electrons

11. A lone pair orbital for O1 with 0.9387 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)

12. A lone pair orbital for C2 with 0.3247 electrons
__made from a p-pi orbital ( 99.94% p 0.06% d)

13. A lone pair orbital for O3 with 0.9903 electrons

14. A lone pair orbital for O3 with 0.8531 electrons
__made from a p-pi orbital ( 99.87% p 0.13% d)

15. A lone pair orbital for O4 with 0.9902 electrons

16. A lone pair orbital for O4 with 0.8761 electrons
__made from a p-pi orbital ( 99.88% p 0.12% d)

-With core pairs on: O 1 C 2 O 3 O 4 -

#### 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, 3, for C2-O3 with the antibonding acceptor orbital, 102, for O3-O4 is 52.7 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-O4 with the antibonding acceptor orbital, 102, for O3-O4 is 100. kJ/mol.

The interaction of bonding donor orbital, 5, for O3-O4 with the antibonding acceptor orbital, 98, for O1-C2 is 154. kJ/mol.

The interaction of bonding donor orbital, 5, for O3-O4 with the antibonding acceptor orbital, 100, for C2-O3 is 37.8 kJ/mol.

The interaction of bonding donor orbital, 5, for O3-O4 with the antibonding acceptor orbital, 101, for C2-O4 is 33.8 kJ/mol.

The interaction of lone pair donor orbital, 10, for O1 with the antibonding acceptor orbital, 101, for C2-O4 is 23.2 kJ/mol.

The interaction of the second lone pair donor orbital, 11, for O1 with the lone pair acceptor orbital, 12, for C2 is 156. kJ/mol.

The interaction of the second lone pair donor orbital, 14, for O3 with the lone pair acceptor orbital, 12, for C2 is 442. kJ/mol.

The interaction of the second lone pair donor orbital, 16, for O4 with the lone pair acceptor orbital, 12, for C2 is 359. 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. Only the spin up electron orbital energies are given.

20 ----- 3.826

19 ----- 2.554

18 ----- -0.184

17 ----- -1.406

16 -^--- -8.550
15 -^-v- -8.645

14 -^-v- -9.378

13 -^-v- -9.740

12 -^-v- -11.25

11 -^-v- -12.92

10 -^-v- -13.05

9 -^-v- -13.74

8 -^-v- -16.84

7 -^-v- -26.15

6 -^-v- -27.22

5 -^-v- -29.65

4 -^-v- -271.9

3 -^-v- -508.6
2 -^-v- -508.6

1 -^-v- -509.1

## 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 = -264.4501534182 Hartrees