H10 H11 | / H9 - C8 H6 \ / H14 C3 - C4 - H5 | / \ O1 - C2 H7 | \ H13 H12
The multiplicity is 2.

## Atomic Charges and Dipole Moment

O1 charge=-0.624
C2 charge= 0.129
C3 charge= 0.162
C4 charge=-0.540
H5 charge= 0.156
H6 charge= 0.157
H7 charge= 0.119
C8 charge=-0.447
H9 charge= 0.119
H10 charge= 0.120
H11 charge= 0.135
H12 charge= 0.022
H13 charge= 0.084
H14 charge= 0.406
with a dipole moment of 1.92544 Debye

## Bond Lengths:

between O1 and C2: distance=1.441 ang___ between O1 and H14: distance=0.975 ang___
between C2 and C3: distance=1.507 ang___ between C2 and C8: distance=2.626 ang___
between C2 and H12: distance=1.120 ang___ between C2 and H13: distance=1.112 ang___
between C3 and C4: distance=1.500 ang___ between C3 and H6: distance=2.168 ang___
between C3 and H7: distance=2.171 ang___ between C3 and C8: distance=1.496 ang___
between C3 and H9: distance=2.160 ang___ between C3 and H11: distance=2.159 ang___
between C3 and H12: distance=2.162 ang___ between C4 and H5: distance=1.115 ang___
between C4 and H6: distance=1.108 ang___ between C4 and H7: distance=1.106 ang___
between C4 and C8: distance=2.599 ang___ between C8 and H9: distance=1.105 ang___
between C8 and H10: distance=1.117 ang___ between C8 and H11: distance=1.107 ang___

## Bond Angles:

for C3-C2-O1: angle=115.8 deg___ for C4-C3-C2: angle=116.8 deg___
for H5-C4-C3: angle=112.4 deg___ for H6-C4-C3: angle=111.6 deg___
for H7-C4-C3: angle=111.9 deg___ for C8-C3-C2: angle=121.8 deg___
for H9-C8-C3: angle=111.3 deg___ for H10-C8-C3: angle=112.8 deg___
for H11-C8-C3: angle=111.1 deg___ for H12-C2-O1: angle=110.1 deg___
for H13-C2-O1: angle=105.0 deg___ for H14-O1-C2: angle=107.8 deg___

## Bond Orders (Mulliken):

between O1 and C2: order=0.855___ between O1 and H14: order=0.867___
between C2 and C3: order=0.818___ between C2 and C8: order=0.128___
between C2 and H12: order=0.987___ between C2 and H13: order=0.987___
between C3 and C4: order=0.697___ between C3 and H6: order=-0.056___
between C3 and H7: order=-0.085___ between C3 and C8: order=0.714___
between C3 and H9: order=-0.076___ between C3 and H11: order=-0.057___
between C3 and H12: order=-0.054___ between C4 and H5: order=0.957___
between C4 and H6: order=1.006___ between C4 and H7: order=1.011___
between C4 and C8: order=-0.073___ between C8 and H9: order=1.009___
between C8 and H10: order=0.954___ between C8 and H11: order=1.007___

## 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 O1-C2 with 0.9978 electrons
__has 66.45% O 1 character in a sp2.44 hybrid
__has 33.55% C 2 character in a s0.90 p3 hybrid

2. A bonding orbital for O1-H14 with 0.9951 electrons
__has 72.94% O 1 character in a s0.77 p3 hybrid
__has 27.06% H14 character in a s orbital

3. A bonding orbital for C2-C3 with 0.9945 electrons
__has 48.70% C 2 character in a sp2.31 hybrid
__has 51.30% C 3 character in a sp2.15 hybrid

4. A bonding orbital for C2-H12 with 0.9964 electrons
__has 55.64% C 2 character in a s0.91 p3 hybrid
__has 44.36% H12 character in a s orbital

5. A bonding orbital for C2-H13 with 0.9944 electrons
__has 56.99% C 2 character in a s0.93 p3 hybrid
__has 43.01% H13 character in a s orbital

6. A bonding orbital for C3-C4 with 0.9947 electrons
__has 51.26% C 3 character in a sp2.01 hybrid
__has 48.74% C 4 character in a sp2.40 hybrid

7. A bonding orbital for C3-C8 with 0.9954 electrons
__has 51.61% C 3 character in a sp1.92 hybrid
__has 48.39% C 8 character in a sp2.43 hybrid

8. A bonding orbital for C4-H5 with 0.9981 electrons
__has 57.27% C 4 character in a s0.89 p3 hybrid
__has 42.73% H 5 character in a s orbital

9. A bonding orbital for C4-H6 with 0.9965 electrons
__has 58.73% C 4 character in a s0.94 p3 hybrid
__has 41.27% H 6 character in a s orbital

10. A bonding orbital for C4-H7 with 0.9954 electrons
__has 59.03% C 4 character in a s0.94 p3 hybrid
__has 40.97% H 7 character in a s orbital

11. A bonding orbital for C8-H9 with 0.9957 electrons
__has 59.88% C 8 character in a s0.96 p3 hybrid
__has 40.12% H 9 character in a s orbital

12. A bonding orbital for C8-H10 with 0.9982 electrons
__has 56.71% C 8 character in a s0.88 p3 hybrid
__has 43.29% H10 character in a s orbital

13. A bonding orbital for C8-H11 with 0.9959 electrons
__has 58.74% C 8 character in a s0.94 p3 hybrid
__has 41.26% H11 character in a s orbital

19. A lone pair orbital for O1 with 0.9929 electrons

20. A lone pair orbital for O1 with 0.9834 electrons

21. A lone pair orbital for C3 with 0.9272 electrons

-With core pairs on: O 1 C 2 C 3 C 4 C 8 -

#### Up Electrons

1. A bonding orbital for O1-C2 with 0.9978 electrons
__has 66.13% O 1 character in a sp2.47 hybrid
__has 33.87% C 2 character in a s0.88 p3 hybrid

2. A bonding orbital for O1-H14 with 0.9954 electrons
__has 72.94% O 1 character in a s0.77 p3 hybrid
__has 27.06% H14 character in a s orbital

3. A bonding orbital for C2-C3 with 0.9953 electrons
__has 53.86% C 2 character in a sp2.18 hybrid
__has 46.14% C 3 character in a sp2.11 hybrid

4. A bonding orbital for C2-H12 with 0.9856 electrons
__has 59.24% C 2 character in a s0.91 p3 hybrid
__has 40.76% H12 character in a s orbital

5. A bonding orbital for C2-H13 with 0.9845 electrons
__has 60.23% C 2 character in a s0.89 p3 hybrid
__has 39.77% H13 character in a s orbital

6. A bonding orbital for C3-C4 with 0.9951 electrons
__has 46.24% C 3 character in a sp1.99 hybrid
__has 53.76% C 4 character in a sp2.28 hybrid

7. A bonding orbital for C3-C8 with 0.9959 electrons
__has 46.46% C 3 character in a sp1.91 hybrid
__has 53.54% C 8 character in a sp2.30 hybrid

8. A bonding orbital for C4-H5 with 0.9854 electrons
__has 61.55% C 4 character in a s0.90 p3 hybrid
__has 38.45% H 5 character in a s orbital

9. A bonding orbital for C4-H6 with 0.9917 electrons
__has 60.65% C 4 character in a s0.90 p3 hybrid
__has 39.35% H 6 character in a s orbital

10. A bonding orbital for C4-H7 with 0.9944 electrons
__has 59.89% C 4 character in a s0.91 p3 hybrid
__has 40.11% H 7 character in a s orbital

11. A bonding orbital for C8-H9 with 0.9937 electrons
__has 60.95% C 8 character in a s0.92 p3 hybrid
__has 39.05% H 9 character in a s orbital

12. A bonding orbital for C8-H10 with 0.9844 electrons
__has 61.51% C 8 character in a s0.89 p3 hybrid
__has 38.49% H10 character in a s orbital

13. A bonding orbital for C8-H11 with 0.9918 electrons
__has 60.60% C 8 character in a s0.91 p3 hybrid
__has 39.40% H11 character in a s orbital

19. A lone pair orbital for O1 with 0.9934 electrons

20. A lone pair orbital for O1 with 0.9852 electrons

-With core pairs on: O 1 C 2 C 3 C 4 C 8 -

#### 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, 8, for C4-H5 with the lone pair acceptor orbital, 21, for C3 is 26.5 kJ/mol.

The interaction of bonding donor orbital, 12, for C8-H10 with the lone pair acceptor orbital, 21, for C3 is 27.7 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 ----- 2.209
24 ----- 2.008

23 ----- 1.453

22 ----- 0.461

21 -^--- -3.609

20 -^-v- -6.492

19 -^-v- -7.927

18 -^-v- -8.650

17 -^-v- -8.957

16 -^-v- -9.373

15 -^-v- -9.656

14 -^-v- -10.21

13 -^-v- -11.07
12 -^-v- -11.16

11 -^-v- -12.26

10 -^-v- -13.56

9 -^-v- -16.69

8 -^-v- -17.06

7 -^-v- -19.63

6 -^-v- -25.21

5 -^-v- -266.1
4 -^-v- -266.1

3 -^-v- -266.6

2 -^-v- -267.5

1 -^-v- -506.4

## 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 = -233.0832868037 Hartrees