H10 H12 \ | H7 C3 - H11 \ / H9 - C1 - C2 H13 / | \ | H8 C6 - O5 C4 - H15 / | \ \ H17 H18 H16 H14
The ion charge is 1. The multiplicity is 2.

## Atomic Charges and Dipole Moment

C1 charge=-0.633
C2 charge= 0.505
C3 charge=-0.520
C4 charge=-0.564
O5 charge=-0.104
C6 charge=-0.215
H7 charge= 0.213
H8 charge= 0.214
H9 charge= 0.227
H10 charge= 0.219
H11 charge= 0.211
H12 charge= 0.219
H13 charge= 0.212
H14 charge= 0.223
H15 charge= 0.200
H16 charge= 0.160
H17 charge= 0.219
H18 charge= 0.211
with a dipole moment of 7.16147 Debye

## Bond Lengths:

between C1 and C2: distance=1.518 ang___ between C1 and H7: distance=1.106 ang___
between C1 and H8: distance=1.107 ang___ between C1 and H9: distance=1.103 ang___
between C2 and C3: distance=1.615 ang___ between C2 and C4: distance=1.558 ang___
between C2 and O5: distance=1.431 ang___ between C3 and H10: distance=1.101 ang___
between C3 and H11: distance=1.100 ang___ between C3 and H12: distance=1.104 ang___
between C4 and H13: distance=1.102 ang___ between C4 and H14: distance=1.104 ang___
between C4 and H15: distance=1.102 ang___ between O5 and C6: distance=1.424 ang___
between C6 and H16: distance=1.104 ang___ between C6 and H17: distance=1.119 ang___
between C6 and H18: distance=1.102 ang___

## Bond Angles:

for C3-C2-C1: angle=111.8 deg___ for C4-C2-C1: angle=114.6 deg___
for O5-C2-C1: angle=116.0 deg___ for C6-O5-C2: angle=122.7 deg___
for H7-C1-C2: angle=113.6 deg___ for H8-C1-C2: angle=111.0 deg___
for H9-C1-C2: angle=108.6 deg___ for H10-C3-C2: angle=108.8 deg___
for H11-C3-C2: angle=110.6 deg___ for H12-C3-C2: angle=104.6 deg___
for H13-C4-C2: angle=108.4 deg___ for H14-C4-C2: angle=108.3 deg___
for H15-C4-C2: angle=111.7 deg___ for H16-C6-O5: angle=112.8 deg___
for H17-C6-O5: angle=107.3 deg___ for H18-C6-O5: angle=106.7 deg___

## Bond Orders (Mulliken):

between C1 and C2: order=0.956___ between C1 and H7: order=0.965___
between C1 and H8: order=0.964___ between C1 and H9: order=0.964___
between C2 and C3: order=0.908___ between C2 and C4: order=0.939___
between C2 and O5: order=0.748___ between C3 and H10: order=0.964___
between C3 and H11: order=0.959___ between C3 and H12: order=0.955___
between C4 and H13: order=0.961___ between C4 and H14: order=0.970___
between C4 and H15: order=0.963___ between O5 and C6: order=0.817___
between C6 and H16: order=0.942___ between C6 and H17: order=0.912___
between C6 and H18: order=0.950___

## 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. *

### Hybridization in the Best Lewis Structure

1. A bonding orbital for O1-C2 with 0.9955 electrons
__has 75.97% O 1 character in a sp1.72 hybrid
__has 24.03% C 2 character in a s0.61 p3 hybrid

2. A bonding orbital for O1-C15 with 0.9964 electrons
__has 73.44% O 1 character in a sp2.43 hybrid
__has 26.56% C15 character in a s0.81 p3 hybrid

3. A bonding orbital for C2-C3 with 0.9946 electrons
__has 51.27% C 2 character in a sp2.16 hybrid
__has 48.73% C 3 character in a sp2.27 hybrid

4. A bonding orbital for C2-C7 with 0.9897 electrons
__has 50.65% C 2 character in a s0.93 p3 hybrid
__has 49.35% C 7 character in a sp2.69 hybrid

5. A bonding orbital for C2-C11 with 0.9902 electrons
__has 51.70% C 2 character in a sp2.62 hybrid
__has 48.30% C11 character in a sp2.44 hybrid

6. A bonding orbital for C3-H4 with 0.9937 electrons
__has 60.08% C 3 character in a s0.92 p3 hybrid
__has 39.92% H 4 character in a s orbital

7. A bonding orbital for C3-H5 with 0.9924 electrons
__has 60.10% C 3 character in a s0.88 p3 hybrid
__has 39.90% H 5 character in a s orbital

8. A bonding orbital for C3-H6 with 0.9877 electrons
__has 61.57% C 3 character in a s0.91 p3 hybrid
__has 38.43% H 6 character in a s orbital

9. A bonding orbital for C7-H8 with 0.9953 electrons
__has 59.89% C 7 character in a s0.96 p3 hybrid
__has 40.11% H 8 character in a s orbital

10. A bonding orbital for C7-H9 with 0.9954 electrons
__has 60.68% C 7 character in a sp2.96 hybrid
__has 39.32% H 9 character in a s orbital

11. A bonding orbital for C7-H10 with 0.9928 electrons
__has 60.44% C 7 character in a s0.92 p3 hybrid
__has 39.56% H10 character in a s orbital

12. A bonding orbital for C11-H12 with 0.9911 electrons
__has 60.65% C11 character in a s0.93 p3 hybrid
__has 39.35% H12 character in a s orbital

13. A bonding orbital for C11-H13 with 0.9941 electrons
__has 59.91% C11 character in a s0.89 p3 hybrid
__has 40.09% H13 character in a s orbital

14. A bonding orbital for C11-H14 with 0.9941 electrons
__has 60.56% C11 character in a s0.96 p3 hybrid
__has 39.44% H14 character in a s orbital

15. A bonding orbital for C15-H16 with 0.9976 electrons
__has 60.04% C15 character in a sp2.59 hybrid
__has 39.96% H16 character in a s orbital

16. A bonding orbital for C15-H17 with 0.9977 electrons
__has 59.13% C15 character in a s0.97 p3 hybrid
__has 40.87% H17 character in a s orbital

17. A bonding orbital for C15-H18 with 0.9960 electrons
__has 60.63% C15 character in a sp2.75 hybrid
__has 39.37% H18 character in a s orbital

24. A lone pair orbital for O1 with 0.9893 electrons

25. A lone pair orbital for O1 with 0.9859 electrons

-With core pairs on: O 1 C 2 C 3 C 7 C11 C15 -

#### 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, 1, for O1-C2 with the antibonding acceptor orbital, 339, for C3-H6 is 1.38 kJ/mol.

The interaction of bonding donor orbital, 1, for O1-C2 with the antibonding acceptor orbital, 342, for C7-H10 is 1.79 kJ/mol.

The interaction of bonding donor orbital, 1, for O1-C2 with the antibonding acceptor orbital, 343, for C11-H12 is 1.84 kJ/mol.

The interaction of bonding donor orbital, 1, for O1-C2 with the antibonding acceptor orbital, 346, for C15-H16 is 1.08 kJ/mol.

The interaction of bonding donor orbital, 2, for O1-C15 with the antibonding acceptor orbital, 335, for C2-C7 is 1.04 kJ/mol.

The interaction of bonding donor orbital, 2, for O1-C15 with the antibonding acceptor orbital, 336, for C2-C11 is 3.30 kJ/mol.

The interaction of bonding donor orbital, 3, for C2-C3 with the antibonding acceptor orbital, 336, for C2-C11 is 1.21 kJ/mol.

The interaction of bonding donor orbital, 3, for C2-C3 with the antibonding acceptor orbital, 341, for C7-H9 is 2.42 kJ/mol.

The interaction of bonding donor orbital, 3, for C2-C3 with the antibonding acceptor orbital, 345, for C11-H14 is 2.88 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-C7 with the antibonding acceptor orbital, 332, for O1-C2 is 1.88 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-C7 with the antibonding acceptor orbital, 333, for O1-C15 is 3.43 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-C7 with the antibonding acceptor orbital, 338, for C3-H5 is 5.56 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-C7 with the antibonding acceptor orbital, 344, for C11-H13 is 4.93 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-C11 with the antibonding acceptor orbital, 333, for O1-C15 is 6.52 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-C11 with the antibonding acceptor orbital, 334, for C2-C3 is 1.21 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-C11 with the antibonding acceptor orbital, 337, for C3-H4 is 4.93 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-C11 with the antibonding acceptor orbital, 340, for C7-H8 is 3.47 kJ/mol.

The interaction of bonding donor orbital, 6, for C3-H4 with the antibonding acceptor orbital, 336, for C2-C11 is 11.9 kJ/mol.

The interaction of bonding donor orbital, 7, for C3-H5 with the antibonding acceptor orbital, 332, for O1-C2 is 1.58 kJ/mol.

The interaction of bonding donor orbital, 7, for C3-H5 with the antibonding acceptor orbital, 335, for C2-C7 is 12.9 kJ/mol.

The interaction of bonding donor orbital, 8, for C3-H6 with the antibonding acceptor orbital, 332, for O1-C2 is 25.8 kJ/mol.

The interaction of bonding donor orbital, 9, for C7-H8 with the antibonding acceptor orbital, 332, for O1-C2 is 1.42 kJ/mol.

The interaction of bonding donor orbital, 9, for C7-H8 with the antibonding acceptor orbital, 336, for C2-C11 is 7.69 kJ/mol.

The interaction of bonding donor orbital, 10, for C7-H9 with the antibonding acceptor orbital, 332, for O1-C2 is 1.67 kJ/mol.

The interaction of bonding donor orbital, 10, for C7-H9 with the antibonding acceptor orbital, 334, for C2-C3 is 8.36 kJ/mol.

The interaction of bonding donor orbital, 11, for C7-H10 with the antibonding acceptor orbital, 332, for O1-C2 is 12.4 kJ/mol.

The interaction of bonding donor orbital, 12, for C11-H12 with the antibonding acceptor orbital, 332, for O1-C2 is 15.8 kJ/mol.

The interaction of bonding donor orbital, 13, for C11-H13 with the antibonding acceptor orbital, 335, for C2-C7 is 10.7 kJ/mol.

The interaction of bonding donor orbital, 14, for C11-H14 with the antibonding acceptor orbital, 332, for O1-C2 is 2.59 kJ/mol.

The interaction of bonding donor orbital, 14, for C11-H14 with the antibonding acceptor orbital, 334, for C2-C3 is 10.8 kJ/mol.

The interaction of bonding donor orbital, 15, for C15-H16 with the antibonding acceptor orbital, 332, for O1-C2 is 1.17 kJ/mol.

The interaction of bonding donor orbital, 15, for C15-H16 with the antibonding acceptor orbital, 333, for O1-C15 is 4.60 kJ/mol.

The interaction of bonding donor orbital, 15, for C15-H16 with the antibonding acceptor orbital, 339, for C3-H6 is 1.25 kJ/mol.

The interaction of bonding donor orbital, 16, for C15-H17 with the antibonding acceptor orbital, 332, for O1-C2 is 3.30 kJ/mol.

The interaction of bonding donor orbital, 16, for C15-H17 with the antibonding acceptor orbital, 333, for O1-C15 is 3.97 kJ/mol.

The interaction of bonding donor orbital, 17, for C15-H18 with the antibonding acceptor orbital, 332, for O1-C2 is 8.91 kJ/mol.

The interaction of bonding donor orbital, 17, for C15-H18 with the antibonding acceptor orbital, 333, for O1-C15 is 2.80 kJ/mol.

The interaction of lone pair donor orbital, 24, for O1 with the antibonding acceptor orbital, 334, for C2-C3 is 13.0 kJ/mol.

The interaction of lone pair donor orbital, 24, for O1 with the antibonding acceptor orbital, 336, for C2-C11 is 1.21 kJ/mol.

The interaction of lone pair donor orbital, 24, for O1 with the antibonding acceptor orbital, 346, for C15-H16 is 6.31 kJ/mol.

The interaction of lone pair donor orbital, 24, for O1 with the antibonding acceptor orbital, 348, for C15-H18 is 5.18 kJ/mol.

The interaction of the second lone pair donor orbital, 25, for O1 with the antibonding acceptor orbital, 335, for C2-C7 is 11.4 kJ/mol.

The interaction of the second lone pair donor orbital, 25, for O1 with the antibonding acceptor orbital, 336, for C2-C11 is 5.31 kJ/mol.

The interaction of the second lone pair donor orbital, 25, for O1 with the antibonding acceptor orbital, 346, for C15-H16 is 2.84 kJ/mol.

The interaction of the second lone pair donor orbital, 25, for O1 with the antibonding acceptor orbital, 347, for C15-H17 is 12.5 kJ/mol.

The interaction of the second lone pair donor orbital, 25, for O1 with the antibonding acceptor orbital, 348, for C15-H18 is 2.67 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.

29 ----- -2.670

28 ----- -2.925

27 ----- -3.552

26 ----- -4.441

25 -^--- -12.47

24 -^-v- -13.54

23 -^-v- -13.83

22 -^-v- -13.96

21 -^-v- -14.11

20 -^-v- -14.45

19 -^-v- -14.72

18 -^-v- -15.00

17 -^-v- -15.67

16 -^-v- -15.83

15 -^-v- -17.39

14 -^-v- -17.59

13 -^-v- -17.69

12 -^-v- -19.56

11 -^-v- -22.01

10 -^-v- -22.20

9 -^-v- -23.07

8 -^-v- -25.61

7 -^-v- -32.96

6 -^-v- -271.2
5 -^-v- -271.2

4 -^-v- -271.7

3 -^-v- -273.2

2 -^-v- -274.3

1 -^-v- -514.7

## 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 = -272.7314864144 Hartrees

*The Lewis Strucutre calculations (NBO analysis) was done without diffuse functions to decrease the size of the calculation.