H12 H4 / | H10 - C9 H6 - C3 - H5 / \ / H11 O1 - C2 | \ H7 H8
The ion charge is 1. The multiplicity is 2.

## Atomic Charges and Dipole Moment

O1 charge=-0.144
C2 charge= 0.304
C3 charge=-0.442
H4 charge= 0.188
H5 charge= 0.172
H6 charge= 0.189
H7 charge= 0.139
H8 charge= 0.139
C9 charge=-0.081
H10 charge= 0.207
H11 charge= 0.207
H12 charge= 0.119
with a dipole moment of 5.01148 Debye

## Bond Lengths:

between O1 and C2: distance=1.417 ang___ between O1 and C9: distance=1.418 ang___
between C2 and C3: distance=1.500 ang___ between C2 and H7: distance=1.129 ang___
between C2 and H8: distance=1.129 ang___ between C3 and H4: distance=1.107 ang___
between C3 and H5: distance=1.103 ang___ between C3 and H6: distance=1.108 ang___
between C9 and H10: distance=1.116 ang___ between C9 and H11: distance=1.115 ang___
between C9 and H12: distance=1.098 ang___

## Bond Angles:

for C3-C2-O1: angle=121.0 deg___ for H4-C3-C2: angle=112.8 deg___
for H5-C3-C2: angle=108.1 deg___ for H6-C3-C2: angle=112.8 deg___
for H7-C2-O1: angle=102.8 deg___ for H8-C2-O1: angle=102.9 deg___
for C9-O1-C2: angle=122.7 deg___ for H10-C9-O1: angle=106.1 deg___
for H11-C9-O1: angle=106.1 deg___ for H12-C9-O1: angle=114.4 deg___

## Bond Orders (Mulliken):

between O1 and C2: order=0.683___ between O1 and C9: order=0.720___
between C2 and C3: order=0.794___ between C2 and H7: order=0.917___
between C2 and H8: order=0.917___ between C3 and H4: order=0.962___
between C3 and H5: order=0.949___ between C3 and H6: order=0.963___
between C9 and H10: order=0.913___ between C9 and H11: order=0.915___
between C9 and H12: order=0.952___

## 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 0.9968 electrons
__has 73.64% O 1 character in a sp2.03 hybrid
__has 26.36% C 2 character in a s0.74 p3 hybrid

2. A bonding orbital for O1-C9 with 0.9973 electrons
__has 73.49% O 1 character in a sp2.18 hybrid
__has 26.51% C 9 character in a s0.77 p3 hybrid

3. A bonding orbital for C2-C3 with 0.9985 electrons
__has 53.07% C 2 character in a sp1.81 hybrid
__has 46.93% C 3 character in a sp2.67 hybrid

4. A bonding orbital for C2-H7 with 0.9935 electrons
__has 60.29% C 2 character in a s0.87 p3 hybrid
__has 39.71% H 7 character in a s orbital

5. A bonding orbital for C2-H8 with 0.9935 electrons
__has 60.30% C 2 character in a s0.87 p3 hybrid
__has 39.70% H 8 character in a s orbital

6. A bonding orbital for C3-H4 with 0.9943 electrons
__has 60.94% C 3 character in a s0.96 p3 hybrid
__has 39.06% H 4 character in a s orbital

7. A bonding orbital for C3-H5 with 0.9876 electrons
__has 62.56% C 3 character in a s0.97 p3 hybrid
__has 37.44% H 5 character in a s orbital

8. A bonding orbital for C3-H6 with 0.9943 electrons
__has 60.92% C 3 character in a s0.96 p3 hybrid
__has 39.08% H 6 character in a s orbital

9. A bonding orbital for C9-H10 with 0.9974 electrons
__has 60.57% C 9 character in a sp2.97 hybrid
__has 39.43% H10 character in a s orbital

10. A bonding orbital for C9-H11 with 0.9973 electrons
__has 60.66% C 9 character in a sp2.94 hybrid
__has 39.34% H11 character in a s orbital

11. A bonding orbital for C9-H12 with 0.9977 electrons
__has 61.28% C 9 character in a sp2.41 hybrid
__has 38.72% H12 character in a s orbital

16. A lone pair orbital for O1 with 0.9892 electrons

17. A lone pair orbital for O1 with 0.9869 electrons
__made from a p-pi orbital ( 99.97% p)

-With core pairs on: O 1 C 2 C 3 C 9 -

#### Up Electrons

1. A bonding orbital for O1-C2 with 0.9970 electrons
__has 69.01% O 1 character in a sp1.96 hybrid
__has 30.99% C 2 character in a s0.76 p3 hybrid

2. A bonding orbital for O1-C9 with 0.9976 electrons
__has 68.82% O 1 character in a sp2.10 hybrid
__has 31.18% C 9 character in a s0.80 p3 hybrid

3. A bonding orbital for C2-C3 with 0.9984 electrons
__has 53.14% C 2 character in a sp1.83 hybrid
__has 46.86% C 3 character in a sp2.67 hybrid

4. A bonding orbital for C2-H7 with 0.9545 electrons
__has 64.51% C 2 character in a s0.86 p3 hybrid
__has 35.49% H 7 character in a s orbital

5. A bonding orbital for C2-H8 with 0.9546 electrons
__has 64.51% C 2 character in a s0.86 p3 hybrid
__has 35.49% H 8 character in a s orbital

6. A bonding orbital for C3-H4 with 0.9943 electrons
__has 61.02% C 3 character in a s0.96 p3 hybrid
__has 38.98% H 4 character in a s orbital

7. A bonding orbital for C3-H5 with 0.9888 electrons
__has 62.41% C 3 character in a s0.96 p3 hybrid
__has 37.59% H 5 character in a s orbital

8. A bonding orbital for C3-H6 with 0.9943 electrons
__has 61.00% C 3 character in a s0.96 p3 hybrid
__has 39.00% H 6 character in a s orbital

9. A bonding orbital for C9-H10 with 0.9669 electrons
__has 64.23% C 9 character in a sp2.99 hybrid
__has 35.77% H10 character in a s orbital

10. A bonding orbital for C9-H11 with 0.9685 electrons
__has 64.12% C 9 character in a sp2.97 hybrid
__has 35.88% H11 character in a s orbital

11. A bonding orbital for C9-H12 with 0.9977 electrons
__has 61.41% C 9 character in a sp2.44 hybrid
__has 38.59% H12 character in a s orbital

16. A lone pair orbital for O1 with 0.9872 electrons

17. A lone pair orbital for O1 with 0.1378 electrons
__made from a p-pi orbital ( 99.93% p 0.07% d)

-With core pairs on: O 1 C 2 C 3 C 9 -

#### 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, 4, for C2-H7 with the second lone pair acceptor orbital, 17, for O1 is 52.5 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-H8 with the second lone pair acceptor orbital, 17, for O1 is 52.3 kJ/mol.

The interaction of bonding donor orbital, 7, for C3-H5 with the antibonding acceptor orbital, 134, for O1-C2 is 20.2 kJ/mol.

The interaction of bonding donor orbital, 9, for C9-H10 with the second lone pair acceptor orbital, 17, for O1 is 42.5 kJ/mol.

The interaction of bonding donor orbital, 10, for C9-H11 with the second lone pair acceptor orbital, 17, for O1 is 39.8 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.

21 ----- -2.928

20 ----- -3.339

19 ----- -3.576

18 ----- -5.024

17 -^--- -13.24

16 -^-v- -14.55

15 -^-v- -14.83

14 -^-v- -14.93

13 -^-v- -15.90

12 -^-v- -16.58

11 -^-v- -18.03

10 -^-v- -18.86

9 -^-v- -19.10

8 -^-v- -20.86

7 -^-v- -23.60

6 -^-v- -25.59

5 -^-v- -33.79

4 -^-v- -271.8

3 -^-v- -273.9

2 -^-v- -274.5

1 -^-v- -515.6

## 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 = -194.0645897745 Hartrees