H11 H10 \ | H6 H7 H9 C3 - H12 \ | | / C1 - C2 - C4 - H13 / / \ H8 H15 - O5 H14
The ion charge is 1. The multiplicity is 2.

## Atomic Charges and Dipole Moment

C1 charge=-0.566
C2 charge= 0.200
C3 charge=-0.686
C4 charge= 0.039
O5 charge=-0.355
H6 charge= 0.251
H7 charge= 0.210
H8 charge= 0.179
H9 charge= 0.158
H10 charge= 0.283
H11 charge= 0.239
H12 charge= 0.216
H13 charge= 0.200
H14 charge= 0.156
H15 charge= 0.471
with a dipole moment of 7.53183 Debye

## Bond Lengths:

between C1 and C2: distance=1.497 ang___ between C1 and C3: distance=2.577 ang___
between C1 and C4: distance=2.729 ang___ between C1 and H6: distance=1.115 ang___
between C1 and H7: distance=1.105 ang___ between C1 and H8: distance=1.102 ang___
between C2 and C3: distance=1.498 ang___ between C2 and C4: distance=1.899 ang___
between C2 and H9: distance=1.105 ang___ between C3 and C4: distance=2.678 ang___
between C3 and H10: distance=1.116 ang___ between C3 and H11: distance=1.104 ang___
between C3 and H12: distance=1.103 ang___ between C4 and O5: distance=1.345 ang___
between C4 and H13: distance=1.100 ang___ between C4 and H14: distance=1.103 ang___
between O5 and H15: distance=0.985 ang___

## Bond Angles:

for C3-C2-C1: angle=118.7 deg___ for C4-C2-C1: angle=106.3 deg___
for O5-C4-C2: angle=109.9 deg___ for H6-C1-C2: angle=106.8 deg___
for H7-C1-C2: angle=113.6 deg___ for H8-C1-C2: angle=113.7 deg___
for H9-C2-C1: angle=114.5 deg___ for H10-C3-C2: angle=106.4 deg___
for H11-C3-C2: angle=113.7 deg___ for H12-C3-C2: angle=113.9 deg___
for H13-C4-C2: angle=98.05 deg___ for H14-C4-C2: angle=99.20 deg___
for H15-O5-C4: angle=112.8 deg___

## Bond Orders (Mulliken):

between C1 and C2: order=0.913___ between C1 and C3: order=-0.118___
between C1 and C4: order=-0.092___ between C1 and H6: order=0.933___
between C1 and H7: order=0.910___ between C1 and H8: order=0.985___
between C2 and C3: order=0.986___ between C2 and C4: order=0.463___
between C2 and H9: order=0.904___ between C3 and C4: order=-0.067___
between C3 and H10: order=0.941___ between C3 and H11: order=0.929___
between C3 and H12: order=0.944___ between C4 and O5: order=1.188___
between C4 and H13: order=0.930___ between C4 and H14: order=0.923___
between O5 and H15: order=0.810___

## 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 0.9962 electrons
__has 48.41% C 1 character in a sp2.33 hybrid
__has 51.59% C 2 character in a sp2.13 hybrid

2. A bonding orbital for C1-H6 with 0.9894 electrons
__has 61.11% C 1 character in a s0.82 p3 hybrid
__has 38.89% H 6 character in a s orbital

3. A bonding orbital for C1-H7 with 0.9948 electrons
__has 60.88% C 1 character in a s0.96 p3 hybrid
__has 39.12% H 7 character in a s orbital

4. A bonding orbital for C1-H8 with 0.9941 electrons
__has 61.10% C 1 character in a s0.96 p3 hybrid
__has 38.90% H 8 character in a s orbital

5. A bonding orbital for C2-C3 with 0.9959 electrons
__has 51.67% C 2 character in a sp2.15 hybrid
__has 48.33% C 3 character in a sp2.34 hybrid

6. A bonding orbital for C2-C4 with 0.9852 electrons
__has 48.56% C 2 character in a s0.41 p3 hybrid
__has 51.44% C 4 character in a s0.63 p3 hybrid

7. A bonding orbital for C2-H9 with 0.9892 electrons
__has 61.68% C 2 character in a s0.97 p3 hybrid
__has 38.32% H 9 character in a s orbital

8. A bonding orbital for C3-H10 with 0.9896 electrons
__has 61.00% C 3 character in a s0.81 p3 hybrid
__has 39.00% H10 character in a s orbital

9. A bonding orbital for C3-H11 with 0.9948 electrons
__has 61.09% C 3 character in a s0.97 p3 hybrid
__has 38.91% H11 character in a s orbital

10. A bonding orbital for C3-H12 with 0.9940 electrons
__has 61.23% C 3 character in a s0.97 p3 hybrid
__has 38.77% H12 character in a s orbital

11. A bonding orbital for C4-O5 with 0.9984 electrons
__has 32.47% C 4 character in a sp2.74 hybrid
__has 67.53% O 5 character in a sp1.96 hybrid

12. A bonding orbital for C4-H13 with 0.9946 electrons
__has 60.88% C 4 character in a sp2.55 hybrid
__has 39.12% H13 character in a s orbital

13. A bonding orbital for C4-H14 with 0.9966 electrons
__has 60.04% C 4 character in a sp2.53 hybrid
__has 39.96% H14 character in a s orbital

14. A bonding orbital for O5-H15 with 0.9943 electrons
__has 76.67% O 5 character in a s0.82 p3 hybrid
__has 23.33% H15 character in a s orbital

20. A lone pair orbital for O5 with 0.9913 electrons

21. A lone pair orbital for O5 with 0.9716 electrons

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

#### Up Electrons

1. A bonding orbital for C1-C2 with 0.9934 electrons
__has 49.26% C 1 character in a sp2.34 hybrid
__has 50.74% C 2 character in a sp1.85 hybrid

2. A bonding orbital for C1-H6 with 0.9619 electrons
__has 63.72% C 1 character in a s0.86 p3 hybrid
__has 36.28% H 6 character in a s orbital

3. A bonding orbital for C1-H7 with 0.9924 electrons
__has 61.35% C 1 character in a s0.93 p3 hybrid
__has 38.65% H 7 character in a s orbital

4. A bonding orbital for C1-H8 with 0.9932 electrons
__has 61.39% C 1 character in a s0.94 p3 hybrid
__has 38.61% H 8 character in a s orbital

5. A bonding orbital for C2-C3 with 0.9923 electrons
__has 51.05% C 2 character in a sp1.84 hybrid
__has 48.95% C 3 character in a sp2.36 hybrid

6. A bonding orbital for C2-H9 with 0.9835 electrons
__has 61.30% C 2 character in a sp2.40 hybrid
__has 38.70% H 9 character in a s orbital

7. A bonding orbital for C3-H10 with 0.9603 electrons
__has 63.67% C 3 character in a s0.86 p3 hybrid
__has 36.33% H10 character in a s orbital

8. A bonding orbital for C3-H11 with 0.9935 electrons
__has 61.38% C 3 character in a s0.94 p3 hybrid
__has 38.62% H11 character in a s orbital

9. A bonding orbital for C3-H12 with 0.9923 electrons
__has 61.54% C 3 character in a s0.94 p3 hybrid
__has 38.46% H12 character in a s orbital

10. A bonding orbital for C4-O5 with 0.9950 electrons
__has 31.46% C 4 character in a s0.98 p3 hybrid
__has 68.54% O 5 character in a sp1.88 hybrid

11. A bonding orbital for C4-O5 with 0.9721 electrons
__has 19.66% C 4 character in a s0.15 p3 hybrid
__has 80.34% O 5 character in a p3 hybrid

12. A bonding orbital for C4-H13 with 0.9820 electrons
__has 61.53% C 4 character in a sp1.82 hybrid
__has 38.47% H13 character in a s orbital

13. A bonding orbital for C4-H14 with 0.9844 electrons
__has 60.93% C 4 character in a sp1.83 hybrid
__has 39.07% H14 character in a s orbital

14. A bonding orbital for O5-H15 with 0.9943 electrons
__has 75.62% O 5 character in a s0.84 p3 hybrid
__has 24.38% H15 character in a s orbital

20. A lone pair orbital for C2 with 0.1255 electrons

21. A lone pair orbital for O5 with 0.9907 electrons

-With core pairs on: C 1 C 2 C 3 C 4 O 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, 2, for C1-H6 with the lone pair acceptor orbital, 20, for C2 is 62.5 kJ/mol.

The interaction of bonding donor orbital, 7, for C3-H10 with the lone pair acceptor orbital, 20, for C2 is 64.2 kJ/mol.

The interaction of bonding donor orbital, 1, for C1-C2 with the second antibonding acceptor orbital, 177, for C4-O5 is 15.3 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-C3 with the antibonding acceptor orbital, 176, for C4-O5 is 2.34 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-C3 with the second antibonding acceptor orbital, 177, for C4-O5 is 12.7 kJ/mol.

The interaction of bonding donor orbital, 6, for C2-H9 with the second antibonding acceptor orbital, 177, for C4-O5 is 26.4 kJ/mol.

The interaction of lone pair donor orbital, 20, for C2 with the second antibonding acceptor orbital, 177, for C4-O5 is 159. kJ/mol.

The interaction of bonding donor orbital, 10, for C4-O5 with the lone pair acceptor orbital, 20, for C2 is 3.51 kJ/mol.

The interaction of the second bonding donor orbital, 11, for C4-O5 with the lone pair acceptor orbital, 20, for C2 is 51.7 kJ/mol.

The interaction of bonding donor orbital, 12, for C4-H13 with the lone pair acceptor orbital, 20, for C2 is 48.8 kJ/mol.

The interaction of bonding donor orbital, 12, for C4-H13 with the antibonding acceptor orbital, 172, for C2-H9 is 2.05 kJ/mol.

The interaction of bonding donor orbital, 13, for C4-H14 with the lone pair acceptor orbital, 20, for C2 is 47.9 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 ----- -2.973

24 ----- -3.599

23 ----- -5.027

22 ----- -5.528

21 -^--- -12.03

20 -^-v- -13.81

19 -^-v- -14.03

18 -^-v- -14.43
17 -^-v- -14.50

16 -^-v- -15.00

15 -^-v- -15.43

14 -^-v- -16.61

13 -^-v- -16.89

12 -^-v- -17.59

11 -^-v- -19.44

10 -^-v- -19.78

9 -^-v- -22.30

8 -^-v- -22.98

7 -^-v- -25.45

6 -^-v- -33.03

5 -^-v- -271.3
4 -^-v- -271.4

3 -^-v- -273.4

2 -^-v- -274.6

1 -^-v- -514.1

## 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 = -233.4058906672 Hartrees