H6 H5 \ / H7 - C4 \ N3 / O1 = C2 H10 \ / C8 - H9 / H11
The multiplicity is 2.

## Atomic Charges and Dipole Moment

O1 charge=-0.499
C2 charge= 0.882
N3 charge=-0.484
C4 charge= 0.034
H5 charge= 0.095
H6 charge= 0.085
H7 charge= 0.041
C8 charge=-0.867
H9 charge= 0.224
H10 charge= 0.246
H11 charge= 0.241
with a dipole moment of 2.04251 Debye

## Bond Lengths:

between O1 and C2: distance=1.258 ang___ between O1 and N3: distance=2.247 ang___
between C2 and N3: distance=1.359 ang___ between C2 and C8: distance=1.508 ang___
between N3 and C4: distance=1.440 ang___ between N3 and C8: distance=2.466 ang___
between C4 and H5: distance=1.108 ang___ between C4 and H6: distance=1.110 ang___
between C4 and H7: distance=1.107 ang___ between C8 and H9: distance=1.105 ang___
between C8 and H10: distance=1.103 ang___ between C8 and H11: distance=1.102 ang___

## Bond Angles:

for N3-C2-O1: angle=118.2 deg___ for C4-N3-C2: angle=121.8 deg___
for H5-C4-N3: angle=107.8 deg___ for H6-C4-N3: angle=110.0 deg___
for H7-C4-N3: angle=113.7 deg___ for C8-C2-O1: angle=122.8 deg___
for H9-C8-C2: angle=109.6 deg___ for H10-C8-C2: angle=111.0 deg___
for H11-C8-C2: angle=109.2 deg___

## Bond Orders (Mulliken):

between O1 and C2: order=1.684___ between O1 and N3: order=-0.124___
between C2 and N3: order=1.216___ between C2 and C8: order=0.770___
between N3 and C4: order=0.790___ between N3 and C8: order=-0.069___
between C4 and H5: order=0.982___ between C4 and H6: order=0.954___
between C4 and H7: order=0.981___ between C8 and H9: order=0.970___
between C8 and H10: order=0.996___ between C8 and H11: order=0.995___

## 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 0.9458 electrons
__has 76.84% O 1 character in a s0.87 p3 hybrid
__has 23.16% C 2 character in a s0.88 p3 d0.95 hybrid

2. A bonding orbital for O1-C2 with 0.9321 electrons
__has 85.89% O 1 character in a s0.50 p3 hybrid
__has 14.11% C 2 character in a s0.84 p3 d2.07 hybrid

3. A bonding orbital for C2-N3 with 0.9898 electrons
__has 38.13% C 2 character in a sp2.29 hybrid
__has 61.87% N 3 character in a sp1.82 hybrid

4. A bonding orbital for C2-N3 with 0.9478 electrons
__has 7.52% C 2 character in a s0.13 p3 d1.70 hybrid
__has 92.48% N 3 character in a p3 hybrid

5. A bonding orbital for C2-C8 with 0.9907 electrons
__has 48.77% C 2 character in a sp1.72 hybrid
__has 51.23% C 8 character in a sp2.76 hybrid

6. A bonding orbital for N3-C4 with 0.9946 electrons
__has 61.59% N 3 character in a sp1.87 hybrid
__has 38.41% C 4 character in a sp2.87 hybrid

7. A bonding orbital for C4-H5 with 0.9965 electrons
__has 58.57% C 4 character in a s0.98 p3 hybrid
__has 41.43% H 5 character in a s orbital

8. A bonding orbital for C4-H6 with 0.9977 electrons
__has 57.99% C 4 character in a s0.90 p3 hybrid
__has 42.01% H 6 character in a s orbital

9. A bonding orbital for C4-H7 with 0.9983 electrons
__has 59.17% C 4 character in a sp2.74 hybrid
__has 40.83% H 7 character in a s orbital

10. A bonding orbital for C8-H9 with 0.9871 electrons
__has 61.38% C 8 character in a s0.96 p3 hybrid
__has 38.62% H 9 character in a s orbital

11. A bonding orbital for C8-H10 with 0.9945 electrons
__has 60.43% C 8 character in a s0.98 p3 hybrid
__has 39.57% H10 character in a s orbital

12. A bonding orbital for C8-H11 with 0.9929 electrons
__has 60.81% C 8 character in a s0.97 p3 hybrid
__has 39.19% H11 character in a s orbital

18. A lone pair orbital for O1 with 0.9912 electrons

19. A lone pair orbital for O1 with 0.9653 electrons

20. A lone pair orbital for N3 with 0.9739 electrons

-With core pairs on: O 1 C 2 N 3 C 4 C 8 -

#### Up Electrons

1. A bonding orbital for O1-C2 with 0.9985 electrons
__has 62.42% O 1 character in a sp1.77 hybrid
__has 37.58% C 2 character in a sp2.22 hybrid

2. A bonding orbital for O1-C2 with 0.9482 electrons
__has 44.05% O 1 character in a p3 hybrid
__has 55.95% C 2 character in a p3 hybrid

3. A bonding orbital for C2-N3 with 0.9963 electrons
__has 43.78% C 2 character in a sp2.11 hybrid
__has 56.22% N 3 character in a sp1.94 hybrid

4. A bonding orbital for C2-C8 with 0.9944 electrons
__has 51.03% C 2 character in a sp1.75 hybrid
__has 48.97% C 8 character in a sp2.82 hybrid

5. A bonding orbital for N3-C4 with 0.9941 electrons
__has 56.71% N 3 character in a sp1.96 hybrid
__has 43.29% C 4 character in a sp2.73 hybrid

6. A bonding orbital for C4-H5 with 0.9881 electrons
__has 60.55% C 4 character in a s0.93 p3 hybrid
__has 39.45% H 5 character in a s orbital

7. A bonding orbital for C4-H6 with 0.9795 electrons
__has 62.25% C 4 character in a s0.95 p3 hybrid
__has 37.75% H 6 character in a s orbital

8. A bonding orbital for C4-H7 with 0.9971 electrons
__has 59.68% C 4 character in a sp2.90 hybrid
__has 40.32% H 7 character in a s orbital

9. A bonding orbital for C8-H9 with 0.9917 electrons
__has 60.10% C 8 character in a s0.96 p3 hybrid
__has 39.90% H 9 character in a s orbital

10. A bonding orbital for C8-H10 with 0.9944 electrons
__has 60.03% C 8 character in a s0.99 p3 hybrid
__has 39.97% H10 character in a s orbital

11. A bonding orbital for C8-H11 with 0.9948 electrons
__has 60.33% C 8 character in a s0.98 p3 hybrid
__has 39.67% H11 character in a s orbital

17. A lone pair orbital for O1 with 0.9903 electrons

18. A lone pair orbital for O1 with 0.9576 electrons

19. A lone pair orbital for N3 with 0.9579 electrons

-With core pairs on: O 1 C 2 N 3 C 4 C 8 -

#### 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 the second bonding donor orbital, 2, for O1-C2 with the second lone pair acceptor orbital, 20, for N3 is 88.9 kJ/mol.

The interaction of bonding donor orbital, 7, for C4-H6 with the second lone pair acceptor orbital, 20, for N3 is 34.7 kJ/mol.

The interaction of the second lone pair donor orbital, 18, for O1 with the antibonding acceptor orbital, 148, for C2-N3 is 53.0 kJ/mol.

The interaction of the second lone pair donor orbital, 18, for O1 with the antibonding acceptor orbital, 149, for C2-C8 is 44.0 kJ/mol.

The interaction of lone pair donor orbital, 19, for N3 with the antibonding acceptor orbital, 146, for O1-C2 is 27.8 kJ/mol.

The interaction of the second lone pair donor orbital, 20, for N3 with the second antibonding acceptor orbital, 147, for O1-C2 is 50.5 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.

24 ----- 2.343

23 ----- 1.712

22 ----- 1.364

21 ----- -1.301

20 -^--- -6.384
19 -^-v- -6.473

18 -^-v- -7.519

17 -^-v- -8.960

16 -^-v- -9.821

15 -^-v- -10.28

14 -^-v- -10.57

13 -^-v- -11.49

12 -^-v- -11.67

11 -^-v- -12.05

10 -^-v- -13.24

9 -^-v- -17.06

8 -^-v- -18.74

7 -^-v- -22.60

6 -^-v- -26.25

5 -^-v- -266.5

4 -^-v- -267.4

3 -^-v- -269.2

2 -^-v- -378.4

1 -^-v- -506.6

## 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 = -247.9393086383 Hartrees