## N=C=O

 N3 = C1 = O2
The multiplicity is 2.

## Atomic Charges and Dipole Moment

C1 charge= 0.683
O2 charge=-0.287
N3 charge=-0.395
with a dipole moment of 0.71686 Debye

## Bond Lengths:

between C1 and O2: distance=1.199 ang___ between C1 and N3: distance=1.236 ang___
between O2 and N3: distance=2.435 ang___

## Bond Angles:

for N3-C1-O2: angle=179.9 deg___

## Bond Orders (Mulliken):

between C1 and O2: order=1.660___ between C1 and N3: order=1.867___
between O2 and N3: order=0.122___

## 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.

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 C1-O2 with 0.9994 electrons
__has 34.51% C 1 character in a sp1.20 hybrid
__has 65.49% O 2 character in a sp1.75 hybrid

2. A bonding orbital for C1-N3 with 0.9992 electrons
__has 44.31% C 1 character in a sp0.83 hybrid
__has 55.69% N 3 character in a sp2.22 hybrid

3. A bonding orbital for C1-N3 with 0.9986 electrons
__has 26.39% C 1 character in a p-pi orbital ( 99.41% p 0.59% d)
__has 73.61% N 3 character in a p-pi orbital ( 99.68% p 0.32% d)

7. A lone pair orbital for C1 with 0.2870 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)

8. A lone pair orbital for O2 with 0.9884 electrons

9. A lone pair orbital for O2 with 0.9068 electrons
__made from a p-pi orbital ( 99.85% p 0.15% d)

10. A lone pair orbital for O2 with 0.8943 electrons
__made from a p-pi orbital ( 99.84% p 0.16% d)

11. A lone pair orbital for N3 with 0.9850 electrons

12. A lone pair orbital for N3 with 0.8017 electrons
__made from a p-pi orbital ( 99.68% p 0.32% d)

72. A antibonding orbital for C1-N3 with 0.1007 electrons
__has 73.61% C 1 character in a p-pi orbital ( 99.41% p 0.59% d)
__has 26.39% N 3 character in a p-pi orbital ( 99.68% p 0.32% d)

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

#### Up Electrons

1. A bonding orbital for C1-O2 with 0.9996 electrons
__has 37.92% C 1 character in a sp1.21 hybrid
__has 62.08% O 2 character in a sp1.71 hybrid

2. A bonding orbital for C1-O2 with 0.9506 electrons
__has 55.93% C 1 character in a p-pi orbital ( 99.83% p 0.17% d)
__has 44.07% O 2 character in a p-pi orbital ( 99.67% p 0.33% d)

3. A bonding orbital for C1-N3 with 0.9995 electrons
__has 48.09% C 1 character in a sp0.82 hybrid
__has 51.91% N 3 character in a sp1.96 hybrid

4. A bonding orbital for C1-N3 with 0.9976 electrons
__has 38.92% C 1 character in a p-pi orbital ( 99.58% p 0.42% d)
__has 61.08% N 3 character in a p-pi orbital ( 99.63% p 0.37% d)

8. A lone pair orbital for O2 with 0.9875 electrons

9. A lone pair orbital for O2 with 0.8952 electrons
__made from a p-pi orbital ( 99.85% p 0.15% d)

10. A lone pair orbital for N3 with 0.9846 electrons

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

#### 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 C1-O2 with the second lone pair acceptor orbital, 11, for N3 is 107. kJ/mol.

The interaction of lone pair donor orbital, 8, for O2 with the antibonding acceptor orbital, 71, for C1-N3 is 37.6 kJ/mol.

The interaction of the second lone pair donor orbital, 9, for O2 with the second antibonding acceptor orbital, 72, for C1-N3 is 231. kJ/mol.

The interaction of lone pair donor orbital, 10, for N3 with the antibonding acceptor orbital, 69, for C1-O2 is 48.4 kJ/mol.

The interaction of the second lone pair donor orbital, 11, for N3 with the second antibonding acceptor orbital, 70, for C1-O2 is 246. 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.

15 ----- 3.713

14 ----- 0.777

13 ----- -0.670

12 ----- -1.244

11 -^--- -8.280

10 -^-v- -9.112

9 -^-v- -10.67

8 -^-v- -12.32

7 -^-v- -12.90

6 -^-v- -13.99

5 -^-v- -24.06

4 -^-v- -28.99

3 -^-v- -270.7

2 -^-v- -379.7

1 -^-v- -509.7

## 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 = -168.0681818876 Hartrees