H9 H8 H6 \ / / C3 - C4 / / \ O1 = C2 H5 H7 \ H10
The ion charge is 1. The multiplicity is 2.

## Atomic Charges and Dipole Moment

O1 charge=-0.021
C2 charge= 0.314
C3 charge=-0.068
C4 charge=-0.373
H5 charge= 0.193
H6 charge= 0.229
H7 charge= 0.160
H8 charge= 0.166
H9 charge= 0.168
H10 charge= 0.231
with a dipole moment of 10.28129 Debye

## Bond Lengths:

between O1 and C2: distance=1.199 ang___ between C2 and C3: distance=1.586 ang___
between C2 and H9: distance=2.186 ang___ between C2 and H10: distance=1.122 ang___
between C3 and C4: distance=1.516 ang___ between C3 and H8: distance=1.115 ang___
between C3 and H9: distance=1.102 ang___ between C4 and H5: distance=1.106 ang___
between C4 and H6: distance=1.120 ang___ between C4 and H7: distance=1.101 ang___

## Bond Angles:

for C3-C2-O1: angle=120.9 deg___ for C4-C3-C2: angle=109.9 deg___
for H5-C4-C3: angle=113.8 deg___ for H6-C4-C3: angle=105.1 deg___
for H7-C4-C3: angle=114.1 deg___ for H8-C3-C2: angle=99.36 deg___
for H9-C3-C2: angle=107.4 deg___ for H10-C2-O1: angle=122.4 deg___

## Bond Orders (Mulliken):

between O1 and C2: order=1.676___ between C2 and C3: order=0.814___
between C2 and H9: order=-0.053___ between C2 and H10: order=0.849___
between C3 and C4: order=0.834___ between C3 and H8: order=0.908___
between C3 and H9: order=0.972___ between C4 and H5: order=0.929___
between C4 and H6: order=0.953___ between C4 and H7: order=0.978___

## 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 0.9913 electrons
__has 78.79% O 1 character in a s0.54 p3 hybrid
__has 21.21% C 2 character in a s0.42 p3 hybrid

2. A bonding orbital for O1-C2 with 0.9903 electrons
__has 75.18% O 1 character in a s0.94 p3 hybrid
__has 24.82% C 2 character in a s0.71 p3 hybrid

3. A bonding orbital for C2-C3 with 0.9957 electrons
__has 52.06% C 2 character in a sp1.74 hybrid
__has 47.94% C 3 character in a s0.73 p3 hybrid

4. A bonding orbital for C2-H10 with 0.9962 electrons
__has 59.09% C 2 character in a sp2.08 hybrid
__has 40.91% H10 character in a s orbital

5. A bonding orbital for C3-C4 with 0.9911 electrons
__has 54.42% C 3 character in a sp2.13 hybrid
__has 45.58% C 4 character in a sp2.63 hybrid

6. A bonding orbital for C3-H8 with 0.9805 electrons
__has 62.55% C 3 character in a s0.88 p3 hybrid
__has 37.45% H 8 character in a s orbital

7. A bonding orbital for C3-H9 with 0.9932 electrons
__has 62.94% C 3 character in a sp2.84 hybrid
__has 37.06% H 9 character in a s orbital

8. A bonding orbital for C4-H5 with 0.9954 electrons
__has 61.19% C 4 character in a s0.98 p3 hybrid
__has 38.81% H 5 character in a s orbital

9. A bonding orbital for C4-H6 with 0.9907 electrons
__has 61.90% C 4 character in a s0.85 p3 hybrid
__has 38.10% H 6 character in a s orbital

10. A bonding orbital for C4-H7 with 0.9956 electrons
__has 60.95% C 4 character in a sp2.89 hybrid
__has 39.05% H 7 character in a s orbital

15. A lone pair orbital for O1 with 0.9936 electrons

16. A lone pair orbital for O1 with 0.9735 electrons

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

#### Up Electrons

1. A bonding orbital for O1-C2 with 0.9989 electrons
__has 65.04% O 1 character in a sp1.40 hybrid
__has 34.96% C 2 character in a sp2.25 hybrid

2. A bonding orbital for O1-C2 with 0.9986 electrons
__has 74.44% O 1 character in a p3 hybrid
__has 25.56% C 2 character in a p3 hybrid

3. A bonding orbital for C2-C3 with 0.9328 electrons
__has 61.60% C 2 character in a sp1.68 hybrid
__has 38.40% C 3 character in a s0.65 p3 hybrid

4. A bonding orbital for C2-H10 with 0.9549 electrons
__has 67.45% C 2 character in a sp2.09 hybrid
__has 32.55% H10 character in a s orbital

5. A bonding orbital for C3-C4 with 0.9881 electrons
__has 54.04% C 3 character in a sp2.05 hybrid
__has 45.96% C 4 character in a sp2.61 hybrid

6. A bonding orbital for C3-H8 with 0.9762 electrons
__has 61.97% C 3 character in a s0.90 p3 hybrid
__has 38.03% H 8 character in a s orbital

7. A bonding orbital for C3-H9 with 0.9941 electrons
__has 62.22% C 3 character in a sp2.78 hybrid
__has 37.78% H 9 character in a s orbital

8. A bonding orbital for C4-H5 with 0.9947 electrons
__has 61.33% C 4 character in a s0.97 p3 hybrid
__has 38.67% H 5 character in a s orbital

9. A bonding orbital for C4-H6 with 0.9843 electrons
__has 62.36% C 4 character in a s0.86 p3 hybrid
__has 37.64% H 6 character in a s orbital

10. A bonding orbital for C4-H7 with 0.9955 electrons
__has 60.95% C 4 character in a sp2.90 hybrid
__has 39.05% H 7 character in a s orbital

15. A lone pair orbital for O1 with 0.9930 electrons

16. A lone pair orbital for O1 with 0.1180 electrons

-With core pairs on: O 1 C 2 C 3 C 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-C3 with the second lone pair acceptor orbital, 16, for O1 is 96.6 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-H10 with the second lone pair acceptor orbital, 16, for O1 is 72.2 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.

20 ----- -3.607
19 ----- -3.691

18 ----- -4.264

17 ----- -9.677

16 -^--- -14.07

15 -^-v- -14.76

14 -^-v- -15.51

13 -^-v- -16.08

12 -^-v- -17.13

11 -^-v- -18.21

10 -^-v- -18.62

9 -^-v- -19.44

8 -^-v- -21.40

7 -^-v- -22.72

6 -^-v- -26.17

5 -^-v- -35.15

4 -^-v- -272.3

3 -^-v- -274.0

2 -^-v- -276.8

1 -^-v- -516.1

## 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 = -192.8535723394 Hartrees