## C=NN triplet

 C3 = N1 - N2
The multiplicity is 3.

## Atomic Charges and Dipole Moment

N1 charge= 0.687
N2 charge=-0.297
C3 charge=-0.390
with a dipole moment of 0.70922 Debye

## Bond Lengths:

between N1 and N2: distance=1.208 ang___ between N1 and C3: distance=1.260 ang___
between N2 and C3: distance=2.468 ang___

## Bond Angles:

for C3-N1-N2: angle=179.9 deg___

## Bond Orders (Mulliken):

between N1 and N2: order=1.195___ between N1 and C3: order=1.564___
between N2 and C3: order=0.056___

## 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 N1-N2 with 0.9991 electrons
__has 55.01% N 1 character in a sp1.26 hybrid
__has 44.99% N 2 character in a sp2.93 hybrid

2. A bonding orbital for N1-C3 with 0.9984 electrons
__has 68.91% N 1 character in a sp0.79 hybrid
__has 31.09% C 3 character in a s0.83 p3 hybrid

3. A bonding orbital for N1-C3 with 0.9972 electrons
__has 50.96% N 1 character in a p-pi orbital ( 99.80% p 0.20% d)
__has 49.04% C 3 character in a p-pi orbital ( 99.44% p 0.56% d)

4. A bonding orbital for N1-C3 with 0.9972 electrons
__has 50.96% N 1 character in a p-pi orbital ( 99.80% p 0.20% d)
__has 49.04% C 3 character in a p-pi orbital ( 99.44% p 0.56% d)

8. A lone pair orbital for N2 with 0.9917 electrons

9. A lone pair orbital for N2 with 0.8901 electrons
__made from a p-pi orbital ( 99.83% p 0.17% d)

10. A lone pair orbital for N2 with 0.8901 electrons
__made from a p-pi orbital ( 99.83% p 0.17% d)

11. A lone pair orbital for C3 with 0.9883 electrons

71. A antibonding orbital for N1-C3 with 0.1056 electrons
__has 49.04% N 1 character in a p-pi orbital ( 99.80% p 0.20% d)
__has 50.96% C 3 character in a p-pi orbital ( 99.44% p 0.56% d)

72. A antibonding orbital for N1-C3 with 0.1056 electrons
__has 49.04% N 1 character in a p-pi orbital ( 99.80% p 0.20% d)
__has 50.96% C 3 character in a p-pi orbital ( 99.44% p 0.56% d)

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

#### Up Electrons

1. A bonding orbital for N1-N2 with 0.9989 electrons
__has 61.95% N 1 character in a sp1.26 hybrid
__has 38.05% N 2 character in a sp2.23 hybrid

2. A bonding orbital for N1-N2 with 0.9513 electrons
__has 87.93% N 1 character in a p-pi orbital ( 99.98% p)
__has 12.07% N 2 character in a p-pi orbital ( 99.30% p 0.70% d)

3. A bonding orbital for N1-N2 with 0.9513 electrons
__has 87.93% N 1 character in a p-pi orbital ( 99.98% p)
__has 12.07% N 2 character in a p-pi orbital ( 99.30% p 0.70% d)

4. A bonding orbital for N1-C3 with 0.9983 electrons
__has 73.05% N 1 character in a sp0.79 hybrid
__has 26.95% C 3 character in a sp2.83 hybrid

8. A lone pair orbital for N2 with 0.9899 electrons

9. A lone pair orbital for C3 with 0.9903 electrons

-With core pairs on: N 1 N 2 C 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 N1-N2 with the second lone pair acceptor orbital, 10, for C3 is 120. kJ/mol.

The interaction of the third bonding donor orbital, 3, for N1-N2 with the third lone pair acceptor orbital, 11, for C3 is 120. kJ/mol.

The interaction of lone pair donor orbital, 8, for N2 with the antibonding acceptor orbital, 72, for N1-C3 is 32.8 kJ/mol.

The interaction of lone pair donor orbital, 9, for C3 with the antibonding acceptor orbital, 69, for N1-N2 is 36.6 kJ/mol.

The interaction of the second lone pair donor orbital, 10, for C3 with the second antibonding acceptor orbital, 70, for N1-N2 is 42.9 kJ/mol.

The interaction of the third lone pair donor orbital, 11, for C3 with the third antibonding acceptor orbital, 71, for N1-N2 is 42.9 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. Only the spin up electron orbital energies are given.

15 ----- 3.780

14 ----- 2.557

13 ----- -1.783 12 ----- -1.784

11 -^--- -7.404 10 -^--- -7.405

9 -^-v- -9.032

8 -^-v- -12.66

7 -^-v- -13.00 6 -^-v- -13.00

5 -^-v- -22.62

4 -^-v- -28.38

3 -^-v- -269.6

2 -^-v- -381.1

1 -^-v- -381.3

## 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 = -147.4958490471 Hartrees