## HNNH->O, Diimine oxide

 H3 H5 \ / 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=-0.582
N2 charge= 0.525
H3 charge= 0.327
O4 charge=-0.411
H5 charge= 0.141
with a dipole moment of 4.21888 Debye

## Bond Lengths:

between N1 and N2: distance=1.284 ang___ between N1 and H3: distance=1.036 ang___
between N2 and O4: distance=1.251 ang___ between N2 and H5: distance=1.051 ang___

## Bond Angles:

for H3-N1-N2: angle=106.3 deg___ for O4-N2-N1: angle=125.6 deg___
for H5-N2-N1: angle=119.3 deg___

## Bond Orders (Mulliken):

between N1 and N2: order=1.722___ between N1 and H3: order=0.880___
between N2 and O4: order=1.295___ between N2 and H5: order=0.856___

## 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 1.9969 electrons
__has 43.49% N 1 character in a sp2.76 hybrid
__has 56.51% N 2 character in a sp1.64 hybrid

2. A bonding orbital for N1-N2 with 1.9954 electrons
__has 52.98% N 1 character in a p-pi orbital ( 99.74% p 0.26% d)
__has 47.02% N 2 character in a p-pi orbital ( 99.82% p 0.18% d)

3. A bonding orbital for N1-H3 with 1.9762 electrons
__has 65.65% N 1 character in a s0.84 p3 hybrid
__has 34.35% H 3 character in a s orbital

4. A bonding orbital for N2-O4 with 1.9966 electrons
__has 51.98% N 2 character in a sp1.89 hybrid
__has 48.02% O 4 character in a s0.83 p3 hybrid

5. A bonding orbital for N2-H5 with 1.9928 electrons
__has 70.06% N 2 character in a sp2.53 hybrid
__has 29.94% H 5 character in a s orbital

9. A lone pair orbital for N1 with 1.9735 electrons
__made from a sp0.93 hybrid

10. A lone pair orbital for O4 with 1.9891 electrons
__made from a sp0.28 hybrid

11. A lone pair orbital for O4 with 1.9279 electrons
__made from a p3 hybrid

12. A lone pair orbital for O4 with 1.6020 electrons
__made from a p-pi orbital ( 99.89% p 0.11% d)

81. A antibonding orbital for N1-N2 with 0.3889 electrons
__has 47.02% N 1 character in a p-pi orbital ( 99.74% p 0.26% d)
__has 52.98% N 2 character in a p-pi orbital ( 99.82% p 0.18% d)

-With core pairs on: N 1 N 2 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 the second bonding donor orbital, 2, for N1-N2 with the second antibonding acceptor orbital, 81, for N1-N2 is 21.1 kJ/mol.

The interaction of bonding donor orbital, 3, for N1-H3 with the antibonding acceptor orbital, 83, for N2-O4 is 50.0 kJ/mol.

The interaction of lone pair donor orbital, 9, for N1 with the antibonding acceptor orbital, 84, for N2-H5 is 39.3 kJ/mol.

The interaction of the second lone pair donor orbital, 11, for O4 with the antibonding acceptor orbital, 80, for N1-N2 is 80.1 kJ/mol.

The interaction of the second lone pair donor orbital, 11, for O4 with the antibonding acceptor orbital, 84, for N2-H5 is 77.6 kJ/mol.

The interaction of the third lone pair donor orbital, 12, for O4 with the second antibonding acceptor orbital, 81, for N1-N2 is 755. 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.

16 ----- 3.893

15 ----- 1.821

14 ----- -0.184

13 ----- -3.113

12 -^-v- -6.900

11 -^-v- -7.170

10 -^-v- -7.946

9 -^-v- -12.27

8 -^-v- -12.55

7 -^-v- -15.18

6 -^-v- -17.62

5 -^-v- -24.42

4 -^-v- -29.47

3 -^-v- -378.6

2 -^-v- -382.7

1 -^-v- -507.2

## 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 = -185.9167259815 Hartrees