H5 H6 | / H8 C4 \ / \ N3 H7 / O1 = C2 H12 \ / C9 - H11 / H10
The ion charge is 1. The multiplicity is 2.

## Atomic Charges and Dipole Moment

O1 charge=-0.233
C2 charge= 0.624
N3 charge=-0.234
C4 charge=-0.232
H5 charge= 0.208
H6 charge= 0.216
H7 charge= 0.159
H8 charge= 0.363
C9 charge=-0.588
H10 charge= 0.254
H11 charge= 0.234
H12 charge= 0.226
with a dipole moment of 12.02107 Debye

## Bond Lengths:

between O1 and C2: distance=1.242 ang___ between C2 and N3: distance=1.414 ang___
between C2 and C9: distance=1.488 ang___ between N3 and C4: distance=1.442 ang___
between N3 and H7: distance=2.106 ang___ between N3 and H8: distance=1.035 ang___
between N3 and C9: distance=2.542 ang___ between C4 and H5: distance=1.115 ang___
between C4 and H6: distance=1.112 ang___ between C4 and H7: distance=1.099 ang___
between C9 and H10: distance=1.101 ang___ between C9 and H11: distance=1.108 ang___
between C9 and H12: distance=1.105 ang___

## Bond Angles:

for N3-C2-O1: angle=112.3 deg___ for C4-N3-C2: angle=124.8 deg___
for H5-C4-N3: angle=111.1 deg___ for H6-C4-N3: angle=108.0 deg___
for H7-C4-N3: angle=111.2 deg___ for H8-N3-C2: angle=113.3 deg___
for C9-C2-O1: angle=125.3 deg___ for H10-C9-C2: angle=109.1 deg___
for H11-C9-C2: angle=109.8 deg___ for H12-C9-C2: angle=111.1 deg___

## Bond Orders (Mulliken):

between O1 and C2: order=1.527___ between C2 and N3: order=0.994___
between C2 and C9: order=0.817___ between N3 and C4: order=0.794___
between N3 and H7: order=-0.052___ between N3 and H8: order=0.806___
between N3 and C9: order=-0.132___ between C4 and H5: order=0.918___
between C4 and H6: order=0.926___ between C4 and H7: order=0.951___
between C9 and H10: order=0.979___ between C9 and H11: order=0.924___
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 0.9916 electrons
__has 84.22% O 1 character in a s0.23 p3 hybrid
__has 15.78% C 2 character in a s0.18 p3 hybrid

2. A bonding orbital for O1-C2 with 0.9866 electrons
__has 69.78% O 1 character in a sp2.39 hybrid
__has 30.22% C 2 character in a sp2.82 hybrid

3. A bonding orbital for C2-N3 with 0.9968 electrons
__has 33.30% C 2 character in a sp2.65 hybrid
__has 66.70% N 3 character in a sp1.88 hybrid

4. A bonding orbital for C2-C9 with 0.9957 electrons
__has 51.41% C 2 character in a sp1.44 hybrid
__has 48.59% C 9 character in a sp2.93 hybrid

5. A bonding orbital for N3-C4 with 0.9960 electrons
__has 66.80% N 3 character in a sp1.77 hybrid
__has 33.20% C 4 character in a s0.91 p3 hybrid

6. A bonding orbital for N3-H8 with 0.9934 electrons
__has 74.68% N 3 character in a sp2.69 hybrid
__has 25.32% H 8 character in a s orbital

7. A bonding orbital for C4-H5 with 0.9975 electrons
__has 60.56% C 4 character in a sp2.98 hybrid
__has 39.44% H 5 character in a s orbital

8. A bonding orbital for C4-H6 with 0.9966 electrons
__has 61.04% C 4 character in a s0.98 p3 hybrid
__has 38.96% H 6 character in a s orbital

9. A bonding orbital for C4-H7 with 0.9956 electrons
__has 61.53% C 4 character in a sp2.69 hybrid
__has 38.47% H 7 character in a s orbital

10. A bonding orbital for C9-H10 with 0.9906 electrons
__has 63.52% C 9 character in a sp2.90 hybrid
__has 36.48% H10 character in a s orbital

11. A bonding orbital for C9-H11 with 0.9808 electrons
__has 63.11% C 9 character in a s0.97 p3 hybrid
__has 36.89% H11 character in a s orbital

12. A bonding orbital for C9-H12 with 0.9895 electrons
__has 61.86% C 9 character in a s0.98 p3 hybrid
__has 38.14% H12 character in a s orbital

18. A lone pair orbital for O1 with 0.9915 electrons

19. A lone pair orbital for O1 with 0.9601 electrons

20. A lone pair orbital for N3 with 0.9525 electrons
__made from a s0.07 p3 hybrid

-With core pairs on: O 1 C 2 N 3 C 4 C 9 -

#### Up Electrons

1. A bonding orbital for O1-C2 with 0.9969 electrons
__has 61.62% O 1 character in a sp1.72 hybrid
__has 38.38% C 2 character in a sp2.16 hybrid

2. A bonding orbital for O1-C2 with 0.8671 electrons
__has 27.88% O 1 character in a p3 hybrid
__has 72.12% C 2 character in a p3 hybrid

3. A bonding orbital for C2-N3 with 0.9966 electrons
__has 38.95% C 2 character in a sp2.60 hybrid
__has 61.05% N 3 character in a sp1.86 hybrid

4. A bonding orbital for C2-C9 with 0.9956 electrons
__has 53.91% C 2 character in a sp1.45 hybrid
__has 46.09% C 9 character in a s0.99 p3 hybrid

5. A bonding orbital for N3-C4 with 0.9972 electrons
__has 62.16% N 3 character in a sp1.69 hybrid
__has 37.84% C 4 character in a s0.95 p3 hybrid

6. A bonding orbital for N3-H8 with 0.9937 electrons
__has 70.47% N 3 character in a sp2.57 hybrid
__has 29.53% H 8 character in a s orbital

7. A bonding orbital for C4-H5 with 0.9694 electrons
__has 64.66% C 4 character in a sp2.93 hybrid
__has 35.34% H 5 character in a s orbital

8. A bonding orbital for C4-H6 with 0.9797 electrons
__has 63.48% C 4 character in a s0.95 p3 hybrid
__has 36.52% H 6 character in a s orbital

9. A bonding orbital for C4-H7 with 0.9946 electrons
__has 62.03% C 4 character in a sp2.75 hybrid
__has 37.97% H 7 character in a s orbital

10. A bonding orbital for C9-H10 with 0.9926 electrons
__has 63.00% C 9 character in a sp2.86 hybrid
__has 37.00% H10 character in a s orbital

11. A bonding orbital for C9-H11 with 0.9917 electrons
__has 61.09% C 9 character in a s0.96 p3 hybrid
__has 38.91% H11 character in a s orbital

12. A bonding orbital for C9-H12 with 0.9929 electrons
__has 61.10% C 9 character in a sp2.97 hybrid
__has 38.90% H12 character in a s orbital

18. A lone pair orbital for O1 with 0.9906 electrons

19. A lone pair orbital for O1 with 0.9451 electrons

20. A lone pair orbital for N3 with 0.1819 electrons

-With core pairs on: O 1 C 2 N 3 C 4 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 the second bonding donor orbital, 2, for O1-C2 with the lone pair acceptor orbital, 20, for N3 is 235. kJ/mol.

The interaction of bonding donor orbital, 7, for C4-H5 with the lone pair acceptor orbital, 20, for N3 is 42.7 kJ/mol.

The interaction of bonding donor orbital, 8, for C4-H6 with the lone pair acceptor orbital, 20, for N3 is 22.8 kJ/mol.

The interaction of the second lone pair donor orbital, 19, for O1 with the antibonding acceptor orbital, 153, for C2-N3 is 71.7 kJ/mol.

The interaction of the second lone pair donor orbital, 19, for O1 with the antibonding acceptor orbital, 154, for C2-C9 is 39.8 kJ/mol.

The interaction of antibonding donor orbital, 153, for C2-N3 with the antibonding acceptor orbital, 154, for C2-C9 is 33.6 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 ----- -3.254

23 ----- -3.527

22 ----- -4.621

21 ----- -7.959

20 -^--- -13.31

19 -^-v- -13.59

18 -^-v- -15.06

17 -^-v- -15.36

16 -^-v- -15.92

15 -^-v- -16.50

14 -^-v- -16.75

13 -^-v- -18.05

12 -^-v- -18.32

11 -^-v- -18.88

10 -^-v- -20.96

9 -^-v- -23.75

8 -^-v- -24.53

7 -^-v- -30.00

6 -^-v- -33.42

5 -^-v- -272.1

4 -^-v- -273.4

3 -^-v- -276.0

2 -^-v- -386.1

1 -^-v- -513.9

## 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 = -248.2775750316 Hartrees