## CN2, N=C=N triplet

 N3 = C1 = N2
The multiplicity is 3.

## Atomic Charges and Dipole Moment

C1 charge= 0.659
N2 charge=-0.329
N3 charge=-0.329
with a dipole moment of 0.00012 Debye

## Bond Lengths:

between C1 and N2: distance=1.241 ang___ between C1 and N3: distance=1.241 ang___
between N2 and N3: distance=2.483 ang___

## Bond Angles:

for N3-C1-N2: angle=179.9 deg___

## Bond Orders (Mulliken):

between C1 and N2: order=1.518___ between C1 and N3: order=1.518___
between N2 and N3: order=0.087___

## 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-N2 with 0.9984 electrons
__has 42.14% C 1 character in a sp1.00 hybrid
__has 57.86% N 2 character in a sp2.04 hybrid

2. A bonding orbital for C1-N3 with 0.9984 electrons
__has 42.14% C 1 character in a sp1.00 hybrid
__has 57.86% N 3 character in a sp2.04 hybrid

6. A lone pair orbital for C1 with 0.2646 electrons
__made from a p-pi orbital (100.00% p)

7. A lone pair orbital for C1 with 0.2646 electrons
__made from a p-pi orbital (100.00% p)

8. A lone pair orbital for N2 with 0.9881 electrons
__made from a sp0.48 hybrid

9. A lone pair orbital for N2 with 0.8659 electrons
__made from a p-pi orbital ( 99.77% p 0.23% d)

10. A lone pair orbital for N2 with 0.8659 electrons
__made from a p-pi orbital ( 99.77% p 0.23% d)

11. A lone pair orbital for N3 with 0.9881 electrons
__made from a sp0.48 hybrid

12. A lone pair orbital for N3 with 0.8659 electrons
__made from a p-pi orbital ( 99.77% p 0.23% d)

13. A lone pair orbital for N3 with 0.8659 electrons
__made from a p-pi orbital ( 99.77% p 0.23% d)

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

#### Up Electrons

1. A bonding orbital for C1-N2 with 0.9993 electrons
__has 50.28% C 1 character in a sp1.00 hybrid
__has 49.72% N 2 character in a sp1.73 hybrid

2. A bonding orbital for C1-N2 with 0.8595 electrons
__has 83.65% C 1 character in a p-pi orbital (100.00% p)
__has 16.35% N 2 character in a p-pi orbital ( 99.53% p 0.47% d)

3. A bonding orbital for C1-N2 with 0.8595 electrons
__has 83.65% C 1 character in a p-pi orbital (100.00% p)
__has 16.35% N 2 character in a p-pi orbital ( 99.53% p 0.47% d)

4. A bonding orbital for C1-N3 with 0.9993 electrons
__has 50.28% C 1 character in a sp1.00 hybrid
__has 49.72% N 3 character in a sp1.73 hybrid

8. A lone pair orbital for N2 with 0.9869 electrons
__made from a sp0.57 hybrid

9. A lone pair orbital for N3 with 0.9869 electrons
__made from a sp0.57 hybrid

10. A lone pair orbital for N3 with 0.1404 electrons
__made from a p-pi orbital ( 99.53% p 0.47% d)

11. A lone pair orbital for N3 with 0.1404 electrons
__made from a p-pi orbital ( 99.53% p 0.47% d)

-With core pairs on: C 1 N 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-N2 with the third lone pair acceptor orbital, 11, for N3 is 329. kJ/mol.

The interaction of the third bonding donor orbital, 3, for C1-N2 with the second lone pair acceptor orbital, 10, for N3 is 329. kJ/mol.

The interaction of lone pair donor orbital, 8, for N2 with the antibonding acceptor orbital, 72, for C1-N3 is 42.8 kJ/mol.

The interaction of lone pair donor orbital, 9, for N3 with the antibonding acceptor orbital, 69, for C1-N2 is 42.8 kJ/mol.

The interaction of the second lone pair donor orbital, 10, for N3 with the third antibonding acceptor orbital, 71, for C1-N2 is 41.5 kJ/mol.

The interaction of the third lone pair donor orbital, 11, for N3 with the second antibonding acceptor orbital, 70, for C1-N2 is 41.5 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 ----- 3.847

14 ----- 1.745

13 ----- -0.686 12 ----- -0.686

11 -^--- -8.359 10 -^--- -8.359

9 -^-v- -10.71

8 -^-v- -11.72
7 -^-v- -11.74 6 -^-v- -11.74

5 -^-v- -23.52

4 -^-v- -25.15

3 -^-v- -269.5

2 -^-v- -380.4 1 -^-v- -380.4

## 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 = -147.5415626657 Hartrees

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