H11 H15 | / H12 - C4 - C5 - H14 | \ H7 O3 H13 \ | H8 - C1 - C2 - H10 / \ H6 H9
The ion charge is 1. The multiplicity is 2.

## Atomic Charges and Dipole Moment

C1 charge=-0.431
C2 charge= 0.180
O3 charge=-0.186
C4 charge= 0.203
C5 charge=-0.462
H6 charge= 0.174
H7 charge= 0.184
H8 charge= 0.182
H9 charge= 0.163
H10 charge= 0.167
H11 charge= 0.163
H12 charge= 0.066
H13 charge= 0.198
H14 charge= 0.198
H15 charge= 0.195
with a dipole moment of 8.45909 Debye

## Bond Lengths:

between C1 and C2: distance=1.504 ang___ between C1 and H6: distance=1.103 ang___
between C1 and H7: distance=1.107 ang___ between C1 and H8: distance=1.107 ang___
between C2 and O3: distance=1.424 ang___ between C2 and C4: distance=2.499 ang___
between C2 and H9: distance=1.125 ang___ between C2 and H10: distance=1.126 ang___
between O3 and C4: distance=1.423 ang___ between C4 and C5: distance=1.564 ang___
between C4 and H11: distance=1.115 ang___ between C4 and H12: distance=1.100 ang___
between C5 and H13: distance=1.102 ang___ between C5 and H14: distance=1.100 ang___
between C5 and H15: distance=1.104 ang___

## Bond Angles:

for O3-C2-C1: angle=120.5 deg___ for C4-O3-C2: angle=122.7 deg___
for C5-C4-O3: angle=108.5 deg___ for H6-C1-C2: angle=107.8 deg___
for H7-C1-C2: angle=112.8 deg___ for H8-C1-C2: angle=112.6 deg___
for H9-C2-C1: angle=114.1 deg___ for H10-C2-C1: angle=113.8 deg___
for H11-C4-O3: angle=104.0 deg___ for H12-C4-O3: angle=112.2 deg___
for H13-C5-C4: angle=109.3 deg___ for H14-C5-C4: angle=111.5 deg___
for H15-C5-C4: angle=106.1 deg___

## Bond Orders (Mulliken):

between C1 and C2: order=0.766___ between C1 and H6: order=0.954___
between C1 and H7: order=0.963___ between C1 and H8: order=0.965___
between C2 and O3: order=0.664___ between C2 and C4: order=0.091___
between C2 and H9: order=0.925___ between C2 and H10: order=0.913___
between O3 and C4: order=0.716___ between C4 and C5: order=0.780___
between C4 and H11: order=0.946___ between C4 and H12: order=0.953___
between C5 and H13: order=0.931___ between C5 and H14: order=0.967___
between C5 and H15: order=0.976___

## 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 0.9984 electrons
__has 47.09% C 1 character in a sp2.68 hybrid
__has 52.91% C 2 character in a sp1.84 hybrid

2. A bonding orbital for C1-H6 with 0.9879 electrons
__has 62.39% C 1 character in a s0.96 p3 hybrid
__has 37.61% H 6 character in a s orbital

3. A bonding orbital for C1-H7 with 0.9945 electrons
__has 60.89% C 1 character in a s0.96 p3 hybrid
__has 39.11% H 7 character in a s orbital

4. A bonding orbital for C1-H8 with 0.9944 electrons
__has 60.78% C 1 character in a s0.96 p3 hybrid
__has 39.22% H 8 character in a s orbital

5. A bonding orbital for C2-O3 with 0.9966 electrons
__has 26.42% C 2 character in a s0.73 p3 hybrid
__has 73.58% O 3 character in a sp2.10 hybrid

6. A bonding orbital for C2-H9 with 0.9937 electrons
__has 60.18% C 2 character in a s0.89 p3 hybrid
__has 39.82% H 9 character in a s orbital

7. A bonding orbital for C2-H10 with 0.9937 electrons
__has 60.21% C 2 character in a s0.88 p3 hybrid
__has 39.79% H10 character in a s orbital

8. A bonding orbital for O3-C4 with 0.9968 electrons
__has 73.93% O 3 character in a sp2.10 hybrid
__has 26.07% C 4 character in a s0.71 p3 hybrid

9. A bonding orbital for C4-C5 with 0.9971 electrons
__has 52.49% C 4 character in a sp2.40 hybrid
__has 47.51% C 5 character in a s0.99 p3 hybrid

10. A bonding orbital for C4-H11 with 0.9942 electrons
__has 60.24% C 4 character in a s0.95 p3 hybrid
__has 39.76% H11 character in a s orbital

11. A bonding orbital for C4-H12 with 0.9955 electrons
__has 60.82% C 4 character in a sp2.61 hybrid
__has 39.18% H12 character in a s orbital

12. A bonding orbital for C5-H13 with 0.9960 electrons
__has 60.61% C 5 character in a s0.99 p3 hybrid
__has 39.39% H13 character in a s orbital

13. A bonding orbital for C5-H14 with 0.9960 electrons
__has 61.50% C 5 character in a sp2.86 hybrid
__has 38.50% H14 character in a s orbital

14. A bonding orbital for C5-H15 with 0.9921 electrons
__has 61.56% C 5 character in a s0.97 p3 hybrid
__has 38.44% H15 character in a s orbital

20. A lone pair orbital for O3 with 0.9894 electrons

21. A lone pair orbital for O3 with 0.9871 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 47.01% C 1 character in a sp2.68 hybrid
__has 52.99% C 2 character in a sp1.87 hybrid

2. A bonding orbital for C1-H6 with 0.9891 electrons
__has 62.24% C 1 character in a s0.96 p3 hybrid
__has 37.76% H 6 character in a s orbital

3. A bonding orbital for C1-H7 with 0.9945 electrons
__has 60.96% C 1 character in a s0.96 p3 hybrid
__has 39.04% H 7 character in a s orbital

4. A bonding orbital for C1-H8 with 0.9945 electrons
__has 60.84% C 1 character in a s0.96 p3 hybrid
__has 39.16% H 8 character in a s orbital

5. A bonding orbital for C2-O3 with 0.9968 electrons
__has 31.10% C 2 character in a s0.76 p3 hybrid
__has 68.90% O 3 character in a sp2.03 hybrid

6. A bonding orbital for C2-H9 with 0.9597 electrons
__has 64.01% C 2 character in a s0.88 p3 hybrid
__has 35.99% H 9 character in a s orbital

7. A bonding orbital for C2-H10 with 0.9588 electrons
__has 64.17% C 2 character in a s0.87 p3 hybrid
__has 35.83% H10 character in a s orbital

8. A bonding orbital for O3-C4 with 0.9970 electrons
__has 69.32% O 3 character in a sp2.03 hybrid
__has 30.68% C 4 character in a s0.74 p3 hybrid

9. A bonding orbital for C4-C5 with 0.9638 electrons
__has 56.55% C 4 character in a sp2.35 hybrid
__has 43.45% C 5 character in a s0.95 p3 hybrid

10. A bonding orbital for C4-H11 with 0.9688 electrons
__has 63.14% C 4 character in a s0.91 p3 hybrid
__has 36.86% H11 character in a s orbital

11. A bonding orbital for C4-H12 with 0.9946 electrons
__has 61.07% C 4 character in a sp2.65 hybrid
__has 38.93% H12 character in a s orbital

12. A bonding orbital for C5-H13 with 0.9957 electrons
__has 60.29% C 5 character in a sp2.96 hybrid
__has 39.71% H13 character in a s orbital

13. A bonding orbital for C5-H14 with 0.9962 electrons
__has 61.09% C 5 character in a sp2.86 hybrid
__has 38.91% H14 character in a s orbital

14. A bonding orbital for C5-H15 with 0.9884 electrons
__has 61.73% C 5 character in a s0.99 p3 hybrid
__has 38.27% H15 character in a s orbital

20. A lone pair orbital for O3 with 0.9874 electrons

21. A lone pair orbital for O3 with 0.1336 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 bonding donor orbital, 6, for C2-H9 with the second lone pair acceptor orbital, 21, for O3 is 46.4 kJ/mol.

The interaction of bonding donor orbital, 7, for C2-H10 with the second lone pair acceptor orbital, 21, for O3 is 48.6 kJ/mol.

The interaction of bonding donor orbital, 9, for C4-C5 with the second lone pair acceptor orbital, 21, for O3 is 39.3 kJ/mol.

The interaction of bonding donor orbital, 10, for C4-H11 with the second lone pair acceptor orbital, 21, for O3 is 34.1 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.

25 ----- -3.010

24 ----- -3.233

23 ----- -3.560

22 ----- -4.502

21 -^--- -12.84

20 -^-v- -13.73

19 -^-v- -14.25

18 -^-v- -14.45

17 -^-v- -14.57

16 -^-v- -14.84

15 -^-v- -15.64

14 -^-v- -16.15

13 -^-v- -17.49

12 -^-v- -18.33

11 -^-v- -18.81

10 -^-v- -19.90

9 -^-v- -21.93

8 -^-v- -23.76

7 -^-v- -25.42

6 -^-v- -33.32

5 -^-v- -271.5
4 -^-v- -271.5

3 -^-v- -273.8

2 -^-v- -274.1

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 = -233.4001888391 Hartrees