## C=N-N=O

 C3 \\ N1 - N2 \\ O4
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

N1 charge= 0.127
N2 charge= 0.168
C3 charge=-0.271
O4 charge=-0.024
with a dipole moment of 2.56326 Debye

## Bond Lengths:

between N1 and N2: distance=1.617 ang___ between N1 and C3: distance=1.205 ang___
between N2 and C3: distance=2.688 ang___ between N2 and O4: distance=1.164 ang___

## Bond Angles:

for C3-N1-N2: angle=144.1 deg___ for O4-N2-N1: angle=113.5 deg___

## Bond Orders (Mulliken):

between N1 and N2: order=0.720___ between N1 and C3: order=2.076___
between N2 and C3: order=0.108___ between N2 and O4: order=1.947___

## 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 N1-N2 with 1.9802 electrons
__has 64.42% N 1 character in a sp1.63 hybrid
__has 35.58% N 2 character in a s0.30 p3 hybrid

2. A bonding orbital for N1-C3 with 1.9842 electrons
__has 69.35% N 1 character in a sp0.63 hybrid
__has 30.65% C 3 character in a sp2.91 hybrid

3. A bonding orbital for N1-C3 with 1.9766 electrons
__has 75.10% N 1 character in a p3 hybrid
__has 24.90% C 3 character in a s0.18 p3 hybrid

4. A bonding orbital for N1-C3 with 1.9590 electrons
__has 75.38% N 1 character in a p3 hybrid
__has 24.62% C 3 character in a p3 hybrid

5. A bonding orbital for N2-O4 with 1.9960 electrons
__has 40.13% N 2 character in a p3 hybrid
__has 59.87% O 4 character in a p3 hybrid

6. A bonding orbital for N2-O4 with 1.9938 electrons
__has 42.57% N 2 character in a sp2.59 hybrid
__has 57.43% O 4 character in a sp2.22 hybrid

11. A lone pair orbital for N2 with 1.9791 electrons

12. A lone pair orbital for C3 with 1.9776 electrons

13. A lone pair orbital for O4 with 1.9909 electrons

14. A lone pair orbital for O4 with 1.8280 electrons

91. A antibonding orbital for N1-N2 with 0.1948 electrons
__has 35.58% N 1 character in a sp1.63 hybrid
__has 64.42% N 2 character in a s0.30 p3 hybrid

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

#### 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 N1-C3 with the second antibonding acceptor orbital, 93, for N1-C3 is 42.5 kJ/mol.

The interaction of the third bonding donor orbital, 4, for N1-C3 with the antibonding acceptor orbital, 95, for N2-O4 is 51.9 kJ/mol.

The interaction of lone pair donor orbital, 11, for N2 with the antibonding acceptor orbital, 92, for N1-C3 is 30.8 kJ/mol.

The interaction of lone pair donor orbital, 12, for C3 with the antibonding acceptor orbital, 91, for N1-N2 is 46.4 kJ/mol.

The interaction of the second lone pair donor orbital, 14, for O4 with the antibonding acceptor orbital, 91, for N1-N2 is 366. kJ/mol.

The interaction of antibonding donor orbital, 91, for N1-N2 with the antibonding acceptor orbital, 92, for N1-C3 is 21.9 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.

18 ----- 0.173

17 ----- -1.054

16 ----- -3.510

15 ----- -5.823

14 -^-v- -7.500

13 -^-v- -8.587

12 -^-v- -9.588

11 -^-v- -10.00

10 -^-v- -13.47

9 -^-v- -14.36

8 -^-v- -15.64

7 -^-v- -18.95

6 -^-v- -23.76

5 -^-v- -32.74

4 -^-v- -268.3

3 -^-v- -379.0

2 -^-v- -383.9

1 -^-v- -511.1

## 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 = -222.7488069449 Hartrees