## H2C=N=N, Diazomethane

 H3 \ C1 - N2 = N5 / H4
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=-1.059
N2 charge= 0.718
H3 charge= 0.364
H4 charge= 0.363
N5 charge=-0.386
with a dipole moment of 1.84618 Debye

## Bond Lengths:

between C1 and N2: distance=1.301 ang___ between C1 and H3: distance=1.089 ang___
between C1 and H4: distance=1.090 ang___ between C1 and N5: distance=2.454 ang___
between N2 and N5: distance=1.153 ang___

## Bond Angles:

for H3-C1-N2: angle=118.1 deg___ for H4-C1-N2: angle=118.1 deg___
for N5-N2-C1: angle=179.9 deg___

## Bond Orders (Mulliken):

between C1 and N2: order=1.395___ between C1 and H3: order=0.975___
between C1 and H4: order=0.975___ between C1 and N5: order=0.214___
between N2 and N5: order=1.996___

## 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-N2 with 1.9932 electrons
__has 34.26% C 1 character in a sp2.35 hybrid
__has 65.74% N 2 character in a sp0.83 hybrid

2. A bonding orbital for C1-N2 with 1.9914 electrons
__has 54.67% C 1 character in a p-pi orbital ( 99.82% p 0.18% d)
__has 45.33% N 2 character in a p-pi orbital ( 99.89% p 0.11% d)

3. A bonding orbital for C1-H3 with 1.9747 electrons
__has 60.57% C 1 character in a sp1.84 hybrid
__has 39.43% H 3 character in a s orbital

4. A bonding orbital for C1-H4 with 1.9747 electrons
__has 60.58% C 1 character in a sp1.84 hybrid
__has 39.42% H 4 character in a s orbital

5. A bonding orbital for N2-N5 with 1.9961 electrons
__has 56.65% N 2 character in a sp1.18 hybrid
__has 43.35% N 5 character in a sp1.95 hybrid

6. A bonding orbital for N2-N5 with 1.9822 electrons
__has 65.33% N 2 character in a p-pi orbital ( 99.85% p 0.15% d)
__has 34.67% N 5 character in a p-pi orbital ( 99.43% p 0.57% d)

10. A lone pair orbital for N5 with 1.9782 electrons

11. A lone pair orbital for N5 with 1.4534 electrons
__made from a p-pi orbital ( 99.75% p 0.25% d)

80. A antibonding orbital for C1-N2 with 0.5338 electrons
__has 45.33% C 1 character in a p-pi orbital ( 99.82% p 0.18% d)
__has 54.67% N 2 character in a p-pi orbital ( 99.89% p 0.11% d)

-With core pairs on: C 1 N 2 N 5 -

#### 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, 1, for C1-N2 with the antibonding acceptor orbital, 83, for N2-N5 is 22.4 kJ/mol.

The interaction of the second bonding donor orbital, 2, for C1-N2 with the second lone pair acceptor orbital, 11, for N5 is 136. kJ/mol.

The interaction of the second bonding donor orbital, 2, for C1-N2 with the second antibonding acceptor orbital, 80, for C1-N2 is 44.0 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-H3 with the antibonding acceptor orbital, 83, for N2-N5 is 29.4 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-H3 with the second antibonding acceptor orbital, 84, for N2-N5 is 32.8 kJ/mol.

The interaction of bonding donor orbital, 4, for C1-H4 with the antibonding acceptor orbital, 83, for N2-N5 is 29.5 kJ/mol.

The interaction of bonding donor orbital, 4, for C1-H4 with the second antibonding acceptor orbital, 84, for N2-N5 is 32.6 kJ/mol.

The interaction of bonding donor orbital, 5, for N2-N5 with the antibonding acceptor orbital, 79, for C1-N2 is 24.7 kJ/mol.

The interaction of the second bonding donor orbital, 6, for N2-N5 with the antibonding acceptor orbital, 81, for C1-H3 is 24.7 kJ/mol.

The interaction of the second bonding donor orbital, 6, for N2-N5 with the antibonding acceptor orbital, 82, for C1-H4 is 24.8 kJ/mol.

The interaction of lone pair donor orbital, 10, for N5 with the antibonding acceptor orbital, 79, for C1-N2 is 75.4 kJ/mol.

The interaction of the second lone pair donor orbital, 11, for N5 with the second antibonding acceptor orbital, 80, for C1-N2 is 1431 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.

15 ----- 2.427

14 ----- 2.155

13 ----- -0.868

12 ----- -2.828

11 -^-v- -5.619

10 -^-v- -9.927

9 -^-v- -10.73

8 -^-v- -11.89

7 -^-v- -13.05

6 -^-v- -13.79

5 -^-v- -21.21

4 -^-v- -27.67

3 -^-v- -267.4

2 -^-v- -379.2

1 -^-v- -381.1

## 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 = -148.8002779722 Hartrees