H11 | H13 - C5 - H12 | H10 - C4 - H9 \ H6 O3 \ / C1 = C2 / \ H7 H8
The ion charge is 1. The multiplicity is 2.

## Atomic Charges and Dipole Moment

C1 charge=-0.217
C2 charge= 0.312
O3 charge=-0.181
C4 charge= 0.158
C5 charge=-0.437
H6 charge= 0.234
H7 charge= 0.219
H8 charge= 0.153
H9 charge= 0.148
H10 charge= 0.073
H11 charge= 0.181
H12 charge= 0.188
H13 charge= 0.166
with a dipole moment of 6.29479 Debye

## Bond Lengths:

between C1 and C2: distance=1.405 ang___ between C1 and H6: distance=1.095 ang___
between C1 and H7: distance=1.096 ang___ between C2 and O3: distance=1.307 ang___
between C2 and C4: distance=2.478 ang___ between C2 and H8: distance=1.100 ang___
between O3 and C4: distance=1.490 ang___ between O3 and C5: distance=2.450 ang___
between C4 and C5: distance=1.524 ang___ between C4 and H9: distance=1.106 ang___
between C4 and H10: distance=1.102 ang___ between C4 and H12: distance=2.188 ang___
between C5 and H9: distance=2.186 ang___ between C5 and H11: distance=1.104 ang___
between C5 and H12: distance=1.102 ang___ between C5 and H13: distance=1.103 ang___

## Bond Angles:

for O3-C2-C1: angle=126.9 deg___ for C4-O3-C2: angle=124.5 deg___
for C5-C4-O3: angle=108.7 deg___ for H6-C1-C2: angle=123.6 deg___
for H7-C1-C2: angle=118.2 deg___ for H8-C2-C1: angle=121.1 deg___
for H9-C4-O3: angle=101.9 deg___ for H10-C4-O3: angle=109.6 deg___
for H11-C5-C4: angle=107.4 deg___ for H12-C5-C4: angle=111.7 deg___
for H13-C5-C4: angle=111.5 deg___

## Bond Orders (Mulliken):

between C1 and C2: order=1.226___ between C1 and H6: order=0.953___
between C1 and H7: order=0.936___ between C2 and O3: order=1.387___
between C2 and C4: order=0.133___ between C2 and H8: order=0.928___
between O3 and C4: order=0.632___ between O3 and C5: order=-0.087___
between C4 and C5: order=0.860___ between C4 and H9: order=0.994___
between C4 and H10: order=0.946___ between C4 and H12: order=-0.051___
between C5 and H9: order=-0.057___ between C5 and H11: order=0.995___
between C5 and H12: order=0.980___ between C5 and H13: order=0.911___

## 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. 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 C1-C2 with 0.9987 electrons
__has 73.13% C 1 character in a p3 hybrid
__has 26.87% C 2 character in a p-pi orbital ( 99.58% p 0.42% d)

2. A bonding orbital for C1-C2 with 0.9983 electrons
__has 49.60% C 1 character in a sp1.84 hybrid
__has 50.40% C 2 character in a sp1.57 hybrid

3. A bonding orbital for C1-H6 with 0.9946 electrons
__has 62.70% C 1 character in a sp2.02 hybrid
__has 37.30% H 6 character in a s orbital

4. A bonding orbital for C1-H7 with 0.9929 electrons
__has 63.32% C 1 character in a sp2.12 hybrid
__has 36.68% H 7 character in a s orbital

5. A bonding orbital for C2-O3 with 0.9981 electrons
__has 31.67% C 2 character in a sp2.42 hybrid
__has 68.33% O 3 character in a sp1.89 hybrid

6. A bonding orbital for C2-H8 with 0.9918 electrons
__has 61.40% C 2 character in a sp2.10 hybrid
__has 38.60% H 8 character in a s orbital

7. A bonding orbital for O3-C4 with 0.9945 electrons
__has 74.60% O 3 character in a sp2.26 hybrid
__has 25.40% C 4 character in a s0.64 p3 hybrid

8. A bonding orbital for C4-C5 with 0.9966 electrons
__has 52.64% C 4 character in a sp2.12 hybrid
__has 47.36% C 5 character in a sp2.75 hybrid

9. A bonding orbital for C4-H9 with 0.9930 electrons
__has 60.78% C 4 character in a s0.98 p3 hybrid
__has 39.22% H 9 character in a s orbital

10. A bonding orbital for C4-H10 with 0.9945 electrons
__has 59.11% C 4 character in a sp2.86 hybrid
__has 40.89% H10 character in a s orbital

11. A bonding orbital for C5-H11 with 0.9901 electrons
__has 61.24% C 5 character in a s0.93 p3 hybrid
__has 38.76% H11 character in a s orbital

12. A bonding orbital for C5-H12 with 0.9950 electrons
__has 61.27% C 5 character in a sp2.97 hybrid
__has 38.73% H12 character in a s orbital

13. A bonding orbital for C5-H13 with 0.9954 electrons
__has 60.08% C 5 character in a s0.97 p3 hybrid
__has 39.92% H13 character in a s orbital

19. A lone pair orbital for O3 with 0.9846 electrons

20. A lone pair orbital for O3 with 0.9290 electrons

-With core pairs on: C 1 C 2 O 3 C 4 C 5 -

#### Up Electrons

1. A bonding orbital for C1-C2 with 0.9983 electrons
__has 46.62% C 1 character in a sp1.87 hybrid
__has 53.38% C 2 character in a sp1.54 hybrid

2. A bonding orbital for C1-H6 with 0.9952 electrons
__has 58.75% C 1 character in a sp2.01 hybrid
__has 41.25% H 6 character in a s orbital

3. A bonding orbital for C1-H7 with 0.9938 electrons
__has 59.34% C 1 character in a sp2.11 hybrid
__has 40.66% H 7 character in a s orbital

4. A bonding orbital for C2-O3 with 0.9981 electrons
__has 33.58% C 2 character in a sp2.41 hybrid
__has 66.42% O 3 character in a sp1.85 hybrid

5. A bonding orbital for C2-O3 with 0.9763 electrons
__has 32.37% C 2 character in a p3 hybrid
__has 67.63% O 3 character in a p-pi orbital ( 99.88% p 0.12% d)

6. A bonding orbital for C2-H8 with 0.9914 electrons
__has 61.67% C 2 character in a sp2.16 hybrid
__has 38.33% H 8 character in a s orbital

7. A bonding orbital for O3-C4 with 0.9946 electrons
__has 72.66% O 3 character in a sp2.22 hybrid
__has 27.34% C 4 character in a s0.65 p3 hybrid

8. A bonding orbital for C4-C5 with 0.9922 electrons
__has 53.15% C 4 character in a sp2.14 hybrid
__has 46.85% C 5 character in a sp2.76 hybrid

9. A bonding orbital for C4-H9 with 0.9886 electrons
__has 61.20% C 4 character in a s0.98 p3 hybrid
__has 38.80% H 9 character in a s orbital

10. A bonding orbital for C4-H10 with 0.9945 electrons
__has 59.22% C 4 character in a sp2.87 hybrid
__has 40.78% H10 character in a s orbital

11. A bonding orbital for C5-H11 with 0.9898 electrons
__has 61.23% C 5 character in a s0.93 p3 hybrid
__has 38.77% H11 character in a s orbital

12. A bonding orbital for C5-H12 with 0.9950 electrons
__has 61.22% C 5 character in a sp2.97 hybrid
__has 38.78% H12 character in a s orbital

13. A bonding orbital for C5-H13 with 0.9952 electrons
__has 60.02% C 5 character in a s0.98 p3 hybrid
__has 39.98% H13 character in a s orbital

20. A lone pair orbital for O3 with 0.9839 electrons

-With core pairs on: C 1 C 2 O 3 C 4 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 the second bonding donor orbital, 5, for C2-O3 with the lone pair acceptor orbital, 19, for C1 is 34.3 kJ/mol.

The interaction of lone pair donor orbital, 20, for O3 with the antibonding acceptor orbital, 156, for C1-C2 is 20.2 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.

24 ----- -3.195

23 ----- -3.751

22 ----- -4.661

21 ----- -7.758

20 -^--- -12.74

19 -^-v- -13.55

18 -^-v- -14.08

17 -^-v- -14.62

16 -^-v- -14.81

15 -^-v- -16.03

14 -^-v- -16.39

13 -^-v- -17.44

12 -^-v- -18.44

11 -^-v- -19.21

10 -^-v- -19.70

9 -^-v- -21.86

8 -^-v- -24.46

7 -^-v- -25.70

6 -^-v- -33.82

5 -^-v- -271.0

4 -^-v- -273.6

3 -^-v- -273.8

2 -^-v- -275.2

1 -^-v- -515.1

## 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 = -232.1934419441 Hartrees