H7 / H9 - C6 H3 | \ / H8 N1 - C2 | \ H5 H4
The multiplicity is 2.

## Atomic Charges and Dipole Moment

N1 charge=-0.454
C2 charge= 0.129
H3 charge= 0.036
H4 charge= 0.023
H5 charge= 0.037
C6 charge= 0.121
H7 charge= 0.039
H8 charge= 0.040
H9 charge= 0.025
with a dipole moment of 2.09964 Debye

## Bond Lengths:

between N1 and C2: distance=1.444 ang___ between N1 and C6: distance=1.445 ang___
between C2 and H3: distance=1.116 ang___ between C2 and H4: distance=1.103 ang___
between C2 and H5: distance=1.116 ang___ between C6 and H7: distance=1.116 ang___
between C6 and H8: distance=1.116 ang___ between C6 and H9: distance=1.103 ang___

## Bond Angles:

for H3-C2-N1: angle=111.5 deg___ for H4-C2-N1: angle=110.7 deg___
for H5-C2-N1: angle=111.6 deg___ for C6-N1-C2: angle=111.9 deg___
for H7-C6-N1: angle=111.6 deg___ for H8-C6-N1: angle=111.6 deg___
for H9-C6-N1: angle=110.6 deg___

## Bond Orders (Mulliken):

between N1 and C2: order=0.853___ between N1 and C6: order=0.853___
between C2 and H3: order=0.969___ between C2 and H4: order=0.985___
between C2 and H5: order=0.969___ between C6 and H7: order=0.969___
between C6 and H8: order=0.969___ between C6 and H9: order=0.985___

## 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 N1-C2 with 0.9959 electrons
__has 59.16% N 1 character in a sp2.56 hybrid
__has 40.84% C 2 character in a sp2.71 hybrid

2. A bonding orbital for N1-C6 with 0.9958 electrons
__has 59.16% N 1 character in a sp2.56 hybrid
__has 40.84% C 6 character in a sp2.71 hybrid

3. A bonding orbital for C2-H3 with 0.9986 electrons
__has 56.94% C 2 character in a s0.94 p3 hybrid
__has 43.06% H 3 character in a s orbital

4. A bonding orbital for C2-H4 with 0.9969 electrons
__has 59.17% C 2 character in a sp2.91 hybrid
__has 40.83% H 4 character in a s orbital

5. A bonding orbital for C2-H5 with 0.9986 electrons
__has 56.93% C 2 character in a s0.94 p3 hybrid
__has 43.07% H 5 character in a s orbital

6. A bonding orbital for C6-H7 with 0.9986 electrons
__has 56.94% C 6 character in a s0.94 p3 hybrid
__has 43.06% H 7 character in a s orbital

7. A bonding orbital for C6-H8 with 0.9986 electrons
__has 56.94% C 6 character in a s0.94 p3 hybrid
__has 43.06% H 8 character in a s orbital

8. A bonding orbital for C6-H9 with 0.9969 electrons
__has 59.17% C 6 character in a sp2.91 hybrid
__has 40.83% H 9 character in a s orbital

12. A lone pair orbital for N1 with 0.9795 electrons

13. A lone pair orbital for N1 with 0.9608 electrons
__made from a p-pi orbital ( 99.94% p 0.06% d)

-With core pairs on: N 1 C 2 C 6 -

#### Up Electrons

1. A bonding orbital for N1-C2 with 0.9964 electrons
__has 54.29% N 1 character in a sp2.30 hybrid
__has 45.71% C 2 character in a sp2.62 hybrid

2. A bonding orbital for N1-C6 with 0.9964 electrons
__has 54.29% N 1 character in a sp2.30 hybrid
__has 45.71% C 6 character in a sp2.62 hybrid

3. A bonding orbital for C2-H3 with 0.9879 electrons
__has 60.57% C 2 character in a s0.94 p3 hybrid
__has 39.43% H 3 character in a s orbital

4. A bonding orbital for C2-H4 with 0.9969 electrons
__has 59.58% C 2 character in a s0.99 p3 hybrid
__has 40.42% H 4 character in a s orbital

5. A bonding orbital for C2-H5 with 0.9879 electrons
__has 60.58% C 2 character in a s0.94 p3 hybrid
__has 39.42% H 5 character in a s orbital

6. A bonding orbital for C6-H7 with 0.9880 electrons
__has 60.57% C 6 character in a s0.94 p3 hybrid
__has 39.43% H 7 character in a s orbital

7. A bonding orbital for C6-H8 with 0.9879 electrons
__has 60.58% C 6 character in a s0.94 p3 hybrid
__has 39.42% H 8 character in a s orbital

8. A bonding orbital for C6-H9 with 0.9969 electrons
__has 59.58% C 6 character in a s0.99 p3 hybrid
__has 40.42% H 9 character in a s orbital

12. A lone pair orbital for N1 with 0.9766 electrons

-With core pairs on: N 1 C 2 C 6 -

#### 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, 3, for C2-H3 with the second lone pair acceptor orbital, 13, for N1 is 20.7 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-H5 with the second lone pair acceptor orbital, 13, for N1 is 20.8 kJ/mol.

The interaction of bonding donor orbital, 6, for C6-H7 with the second lone pair acceptor orbital, 13, for N1 is 20.7 kJ/mol.

The interaction of bonding donor orbital, 7, for C6-H8 with the second lone pair acceptor orbital, 13, for N1 is 20.8 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.

17 ----- 3.112

16 ----- 2.064

15 ----- 1.828

14 ----- 1.401

13 -^--- -5.406

12 -^-v- -6.136

11 -^-v- -8.955

10 -^-v- -9.564

9 -^-v- -11.05
8 -^-v- -11.11

7 -^-v- -11.33

6 -^-v- -14.74

5 -^-v- -17.39

4 -^-v- -22.27

3 -^-v- -266.8 2 -^-v- -266.8

1 -^-v- -377.6

## 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 = -134.5492730029 Hartrees