H4 \ H16 H14 H15 H6 - C3 - H5 \ | / / H10 C13 - C1 - C2 \ / | \ C9 - H11 H8 H7 | H12
The multiplicity is 2.

## Atomic Charges and Dipole Moment

C1 charge= 0.222
C2 charge= 0.009
C3 charge=-0.337
H4 charge= 0.090
H5 charge= 0.093
H6 charge= 0.077
H7 charge= 0.025
H8 charge= 0.038
C9 charge=-0.605
H10 charge= 0.172
H11 charge= 0.157
H12 charge= 0.154
C13 charge=-0.536
H14 charge= 0.153
H15 charge= 0.141
H16 charge= 0.143
with a dipole moment of 0.30867 Debye

## Bond Lengths:

between C1 and C2: distance=1.509 ang___ between C1 and C9: distance=1.501 ang___
between C1 and C13: distance=1.503 ang___ between C2 and C3: distance=1.554 ang___
between C2 and H7: distance=1.114 ang___ between C2 and H8: distance=1.107 ang___
between C3 and H4: distance=1.104 ang___ between C3 and H5: distance=1.105 ang___
between C3 and H6: distance=1.104 ang___ between C9 and H10: distance=1.106 ang___
between C9 and H11: distance=1.106 ang___ between C9 and H12: distance=1.117 ang___
between C13 and H14: distance=1.116 ang___ between C13 and H15: distance=1.106 ang___
between C13 and H16: distance=1.107 ang___

## Bond Angles:

for C3-C2-C1: angle=114.4 deg___ for H4-C3-C2: angle=111.1 deg___
for H5-C3-C2: angle=110.9 deg___ for H6-C3-C2: angle=110.8 deg___
for H7-C2-C1: angle=109.7 deg___ for H8-C2-C1: angle=109.5 deg___
for C9-C1-C2: angle=119.9 deg___ for H10-C9-C1: angle=111.8 deg___
for H11-C9-C1: angle=112.0 deg___ for H12-C9-C1: angle=112.0 deg___
for C13-C1-C2: angle=119.3 deg___ for H14-C13-C1: angle=111.6 deg___
for H15-C13-C1: angle=112.4 deg___ for H16-C13-C1: angle=111.9 deg___

## Bond Orders (Mulliken):

between C1 and C2: order=0.905___ between C1 and C9: order=0.897___
between C1 and C13: order=0.903___ between C2 and C3: order=0.936___
between C2 and H7: order=0.987___ between C2 and H8: order=0.996___
between C3 and H4: order=0.982___ between C3 and H5: order=0.984___
between C3 and H6: order=0.983___ between C9 and H10: order=0.991___
between C9 and H11: order=0.992___ between C9 and H12: order=0.975___
between C13 and H14: order=0.975___ between C13 and H15: order=0.992___
between C13 and H16: order=0.989___

## 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 C1-C2 with 0.9919 electrons
__has 50.18% C 1 character in a sp2.04 hybrid
__has 49.82% C 2 character in a sp2.34 hybrid

2. A bonding orbital for C1-C9 with 0.9935 electrons
__has 50.05% C 1 character in a sp2.08 hybrid
__has 49.95% C 9 character in a sp2.12 hybrid

3. A bonding orbital for C1-C13 with 0.9935 electrons
__has 49.83% C 1 character in a sp2.13 hybrid
__has 50.17% C13 character in a sp2.13 hybrid

4. A bonding orbital for C2-C3 with 0.9955 electrons
__has 49.13% C 2 character in a sp2.55 hybrid
__has 50.87% C 3 character in a sp2.30 hybrid

5. A bonding orbital for C2-H7 with 0.9929 electrons
__has 56.68% C 2 character in a s0.78 p3 hybrid
__has 43.32% H 7 character in a s orbital

6. A bonding orbital for C2-H8 with 0.9911 electrons
__has 58.08% C 2 character in a s0.82 p3 hybrid
__has 41.92% H 8 character in a s orbital

7. A bonding orbital for C3-H4 with 0.9956 electrons
__has 58.56% C 3 character in a s0.91 p3 hybrid
__has 41.44% H 4 character in a s orbital

8. A bonding orbital for C3-H5 with 0.9953 electrons
__has 58.55% C 3 character in a s0.90 p3 hybrid
__has 41.45% H 5 character in a s orbital

9. A bonding orbital for C3-H6 with 0.9957 electrons
__has 58.64% C 3 character in a s0.91 p3 hybrid
__has 41.36% H 6 character in a s orbital

10. A bonding orbital for C9-H10 with 0.9951 electrons
__has 58.20% C 9 character in a s0.90 p3 hybrid
__has 41.80% H10 character in a s orbital

11. A bonding orbital for C9-H11 with 0.9953 electrons
__has 58.23% C 9 character in a s0.91 p3 hybrid
__has 41.77% H11 character in a s orbital

12. A bonding orbital for C9-H12 with 0.9980 electrons
__has 56.21% C 9 character in a s0.83 p3 hybrid
__has 43.79% H12 character in a s orbital

13. A bonding orbital for C13-H14 with 0.9979 electrons
__has 56.34% C13 character in a s0.83 p3 hybrid
__has 43.66% H14 character in a s orbital

14. A bonding orbital for C13-H15 with 0.9950 electrons
__has 58.38% C13 character in a s0.91 p3 hybrid
__has 41.62% H15 character in a s orbital

15. A bonding orbital for C13-H16 with 0.9954 electrons
__has 58.11% C13 character in a s0.90 p3 hybrid
__has 41.89% H16 character in a s orbital

21. A lone pair orbital for C1 with 0.9206 electrons
__made from a s0.09 p3 hybrid

-With core pairs on: C 1 C 2 C 3 C 9 C13 -

#### 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 C1-C2 with the antibonding acceptor orbital, 297, for C3-H5 is 3.13 kJ/mol.

The interaction of bonding donor orbital, 1, for C1-C2 with the antibonding acceptor orbital, 299, for C9-H10 is 3.84 kJ/mol.

The interaction of bonding donor orbital, 1, for C1-C2 with the antibonding acceptor orbital, 304, for C13-H16 is 3.80 kJ/mol.

The interaction of bonding donor orbital, 2, for C1-C9 with the antibonding acceptor orbital, 293, for C2-C3 is 3.22 kJ/mol.

The interaction of bonding donor orbital, 2, for C1-C9 with the antibonding acceptor orbital, 294, for C2-H7 is 1.17 kJ/mol.

The interaction of bonding donor orbital, 2, for C1-C9 with the antibonding acceptor orbital, 295, for C2-H8 is 1.54 kJ/mol.

The interaction of bonding donor orbital, 2, for C1-C9 with the antibonding acceptor orbital, 303, for C13-H15 is 4.39 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C13 with the antibonding acceptor orbital, 295, for C2-H8 is 3.80 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C13 with the antibonding acceptor orbital, 300, for C9-H11 is 4.26 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-C3 with the antibonding acceptor orbital, 290, for C1-C2 is 1.29 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-C3 with the antibonding acceptor orbital, 291, for C1-C9 is 4.76 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-H7 with the antibonding acceptor orbital, 291, for C1-C9 is 4.56 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-H7 with the antibonding acceptor orbital, 298, for C3-H6 is 7.53 kJ/mol.

The interaction of bonding donor orbital, 6, for C2-H8 with the antibonding acceptor orbital, 292, for C1-C13 is 11.8 kJ/mol.

The interaction of bonding donor orbital, 6, for C2-H8 with the antibonding acceptor orbital, 296, for C3-H4 is 7.28 kJ/mol.

The interaction of bonding donor orbital, 7, for C3-H4 with the antibonding acceptor orbital, 295, for C2-H8 is 6.86 kJ/mol.

The interaction of bonding donor orbital, 8, for C3-H5 with the antibonding acceptor orbital, 290, for C1-C2 is 9.03 kJ/mol.

The interaction of bonding donor orbital, 9, for C3-H6 with the antibonding acceptor orbital, 294, for C2-H7 is 6.90 kJ/mol.

The interaction of bonding donor orbital, 10, for C9-H10 with the antibonding acceptor orbital, 290, for C1-C2 is 11.6 kJ/mol.

The interaction of bonding donor orbital, 11, for C9-H11 with the antibonding acceptor orbital, 292, for C1-C13 is 11.4 kJ/mol.

The interaction of bonding donor orbital, 13, for C13-H14 with the antibonding acceptor orbital, 290, for C1-C2 is 1.12 kJ/mol.

The interaction of bonding donor orbital, 14, for C13-H15 with the antibonding acceptor orbital, 291, for C1-C9 is 11.7 kJ/mol.

The interaction of bonding donor orbital, 15, for C13-H16 with the antibonding acceptor orbital, 290, for C1-C2 is 10.8 kJ/mol.

The interaction of lone pair donor orbital, 21, for C1 with the antibonding acceptor orbital, 293, for C2-C3 is 19.1 kJ/mol.

The interaction of lone pair donor orbital, 21, for C1 with the antibonding acceptor orbital, 294, for C2-H7 is 24.3 kJ/mol.

The interaction of lone pair donor orbital, 21, for C1 with the antibonding acceptor orbital, 297, for C3-H5 is 2.21 kJ/mol.

The interaction of lone pair donor orbital, 21, for C1 with the antibonding acceptor orbital, 299, for C9-H10 is 7.07 kJ/mol.

The interaction of lone pair donor orbital, 21, for C1 with the antibonding acceptor orbital, 300, for C9-H11 is 6.40 kJ/mol.

The interaction of lone pair donor orbital, 21, for C1 with the antibonding acceptor orbital, 301, for C9-H12 is 37.4 kJ/mol.

The interaction of lone pair donor orbital, 21, for C1 with the antibonding acceptor orbital, 302, for C13-H14 is 36.1 kJ/mol.

The interaction of lone pair donor orbital, 21, for C1 with the antibonding acceptor orbital, 303, for C13-H15 is 3.80 kJ/mol.

The interaction of lone pair donor orbital, 21, for C1 with the antibonding acceptor orbital, 304, for C13-H16 is 9.74 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 ----- 2.135
24 ----- 2.026

23 ----- 1.647

22 ----- 1.355

21 -^--- -3.547

20 -^-v- -7.772

19 -^-v- -7.912

18 -^-v- -8.507

17 -^-v- -8.716

16 -^-v- -9.200

15 -^-v- -9.307

14 -^-v- -9.681

13 -^-v- -10.46

12 -^-v- -10.93

11 -^-v- -11.06

10 -^-v- -12.78

9 -^-v- -15.22

8 -^-v- -16.79

7 -^-v- -17.90

6 -^-v- -19.76

5 -^-v- -265.9
4 -^-v- -265.9 3 -^-v- -265.9

2 -^-v- -266.1

1 -^-v- -266.5

## 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 = -197.1607968756 Hartrees

*Please note that the NBO analysis was run without diffuse functions to decrease the size of the calculation.