## C4N2

 N3 C6 \ // || || C1 = C2 - N5 // C4
Tell me about the atomic charges, dipole moment, bond lengths, angles, bond orders,
molecular orbital energies, or total energy.
Tell me about the best Lewis structure.

## Atomic Charges and Dipole Moment

C1 charge= 0.170
C2 charge= 0.171
N3 charge=-0.043
C4 charge=-0.126
N5 charge=-0.043
C6 charge=-0.128
with a dipole moment of 0.44087 Debye

## Bond Lengths:

between C1 and C2: distance=1.287 ang___ between C1 and N3: distance=1.409 ang___
between C1 and C4: distance=1.519 ang___ between C1 and N5: distance=2.614 ang___
between C1 and C6: distance=2.746 ang___ between C2 and N3: distance=2.615 ang___
between C2 and C4: distance=2.745 ang___ between C2 and N5: distance=1.409 ang___
between C2 and C6: distance=1.519 ang___ between N3 and C4: distance=1.290 ang___
between N5 and C6: distance=1.290 ang___

## Bond Angles:

for N3-C1-C2: angle=151.7 deg___ for C4-C1-C2: angle=155.9 deg___
for N5-C2-C1: angle=151.5 deg___ for C6-C2-C1: angle=156.1 deg___

## Bond Orders (Mulliken):

between C1 and C2: order=1.354___ between C1 and N3: order=1.019___
between C1 and C4: order=1.339___ between C1 and N5: order=-0.071___
between C1 and C6: order=-0.266___ between C2 and N3: order=-0.069___
between C2 and C4: order=-0.270___ between C2 and N5: order=1.020___
between C2 and C6: order=1.334___ between N3 and C4: order=1.554___
between N5 and C6: order=1.555___

## 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. Please note that your structure can't be well described by a single Lewis structure, because of extensive delocalization.

### Hybridization in the Best Lewis Structure

1. A bonding orbital for C1-C2 with 1.9863 electrons
__has 50.00% C 1 character in a sp1.06 hybrid
__has 50.00% C 2 character in a sp1.06 hybrid

2. A bonding orbital for C1-N3 with 1.8876 electrons
__has 50.21% C 1 character in a sp2.60 hybrid
__has 49.79% N 3 character in a s0.53 p3 hybrid

3. A bonding orbital for C1-C4 with 1.7995 electrons
__has 68.95% C 1 character in a s0.92 p3 hybrid
__has 31.05% C 4 character in a s0.35 p3 hybrid

4. A bonding orbital for C2-N5 with 1.8874 electrons
__has 50.20% C 2 character in a sp2.61 hybrid
__has 49.80% N 5 character in a s0.53 p3 hybrid

5. A bonding orbital for C2-C6 with 1.7998 electrons
__has 68.96% C 2 character in a s0.93 p3 hybrid
__has 31.04% C 6 character in a s0.36 p3 hybrid

6. A bonding orbital for N3-C4 with 1.9765 electrons
__has 63.98% N 3 character in a sp2.03 hybrid
__has 36.02% C 4 character in a s0.98 p3 hybrid

7. A bonding orbital for N3-C4 with 1.6538 electrons
__has 70.80% N 3 character in a p-pi orbital ( 99.50% p 0.50% d)
__has 29.20% C 4 character in a p-pi orbital ( 98.88% p 1.11% d)

8. A bonding orbital for N5-C6 with 1.9765 electrons
__has 63.98% N 5 character in a sp2.02 hybrid
__has 36.02% C 6 character in a s0.98 p3 hybrid

9. A bonding orbital for N5-C6 with 1.6539 electrons
__has 70.78% N 5 character in a p-pi orbital ( 99.50% p 0.50% d)
__has 29.22% C 6 character in a p-pi orbital ( 98.88% p 1.11% d)

16. A lone pair orbital for C1 with 0.6298 electrons

17. A lone pair orbital for C2 with 0.6298 electrons

18. A lone pair orbital for N3 with 1.9601 electrons

19. A lone pair orbital for C4 with 1.9502 electrons

20. A lone pair orbital for N5 with 1.9601 electrons

21. A lone pair orbital for C6 with 1.9500 electrons

-With core pairs on: C 1 C 2 N 3 C 4 N 5 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, 2, for C1-N3 with the lone pair acceptor orbital, 17, for C2 is 43.6 kJ/mol.

The interaction of bonding donor orbital, 2, for C1-N3 with the antibonding acceptor orbital, 138, for C1-C4 is 84.7 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C4 with the lone pair acceptor orbital, 17, for C2 is 178. kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C4 with the antibonding acceptor orbital, 137, for C1-N3 is 30.7 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-N5 with the lone pair acceptor orbital, 16, for C1 is 43.8 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-N5 with the antibonding acceptor orbital, 140, for C2-C6 is 84.8 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-C6 with the lone pair acceptor orbital, 16, for C1 is 177. kJ/mol.

The interaction of bonding donor orbital, 5, for C2-C6 with the antibonding acceptor orbital, 139, for C2-N5 is 30.7 kJ/mol.

The interaction of bonding donor orbital, 6, for N3-C4 with the antibonding acceptor orbital, 136, for C1-C2 is 88.7 kJ/mol.

The interaction of the second bonding donor orbital, 7, for N3-C4 with the lone pair acceptor orbital, 16, for C1 is 863. kJ/mol.

The interaction of bonding donor orbital, 8, for N5-C6 with the antibonding acceptor orbital, 136, for C1-C2 is 88.7 kJ/mol.

The interaction of the second bonding donor orbital, 9, for N5-C6 with the lone pair acceptor orbital, 17, for C2 is 863. kJ/mol.

The interaction of lone pair donor orbital, 16, for C1 with the antibonding acceptor orbital, 139, for C2-N5 is 59.4 kJ/mol.

The interaction of lone pair donor orbital, 16, for C1 with the antibonding acceptor orbital, 140, for C2-C6 is 52.9 kJ/mol.

The interaction of lone pair donor orbital, 17, for C2 with the antibonding acceptor orbital, 137, for C1-N3 is 59.2 kJ/mol.

The interaction of lone pair donor orbital, 17, for C2 with the antibonding acceptor orbital, 138, for C1-C4 is 53.1 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.

23 ----- -2.958
22 ----- -3.056

21 ----- -4.085
20 ----- -4.158

19 -^-v- -7.682 18 -^-v- -7.686

17 -^-v- -8.787

16 -^-v- -8.970

15 -^-v- -11.93 14 -^-v- -11.94

13 -^-v- -13.43

12 -^-v- -14.36
11 -^-v- -14.38

10 -^-v- -14.51

9 -^-v- -20.06

8 -^-v- -27.24

7 -^-v- -27.43

6 -^-v- -269.6 5 -^-v- -269.6

4 -^-v- -270.2
3 -^-v- -270.3

2 -^-v- -380.3 1 -^-v- -380.3

## 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 = -261.7292419225 Hartrees