## CH3NN+, diazomethane cation

 H3 \ H5 - C1 - N2 E N6 / H4
The ion charge is 1.

## Atomic Charges and Dipole Moment

C1 charge=-0.506
N2 charge= 0.509
H3 charge= 0.302
H4 charge= 0.303
H5 charge= 0.302
N6 charge= 0.088
with a dipole moment of 3.10935 Debye

## Bond Lengths:

between C1 and N2: distance=1.427 ang___ between C1 and H3: distance=1.107 ang___
between C1 and H4: distance=1.107 ang___ between C1 and H5: distance=1.107 ang___
between C1 and N6: distance=2.541 ang___ between N2 and N6: distance=1.114 ang___

## Bond Angles:

for H3-C1-N2: angle=107.4 deg___ for H4-C1-N2: angle=107.4 deg___
for H5-C1-N2: angle=107.3 deg___ for N6-N2-C1: angle=179.8 deg___

## Bond Orders (Mulliken):

between C1 and N2: order=0.718___ between C1 and H3: order=0.899___
between C1 and H4: order=0.898___ between C1 and H5: order=0.899___
between C1 and N6: order=0.078___ between N2 and N6: order=2.588___

## 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.

### Hybridization in the Best Lewis Structure

1. A bonding orbital for C1-N2 with 1.9948 electrons
__has 31.04% C 1 character in a s0.76 p3 hybrid
__has 68.96% N 2 character in a sp0.84 hybrid

2. A bonding orbital for C1-H3 with 1.9685 electrons
__has 64.00% C 1 character in a sp2.74 hybrid
__has 36.00% H 3 character in a s orbital

3. A bonding orbital for C1-H4 with 1.9685 electrons
__has 63.99% C 1 character in a sp2.75 hybrid
__has 36.01% H 4 character in a s orbital

4. A bonding orbital for C1-H5 with 1.9685 electrons
__has 63.99% C 1 character in a sp2.75 hybrid
__has 36.01% H 5 character in a s orbital

5. A bonding orbital for N2-N6 with 1.9985 electrons
__has 55.32% N 2 character in a sp1.16 hybrid
__has 44.68% N 6 character in a sp1.83 hybrid

6. A bonding orbital for N2-N6 with 1.9940 electrons
__has 58.72% N 2 character in a p-pi orbital ( 99.76% p 0.24% d)
__has 41.28% N 6 character in a p-pi orbital ( 99.38% p 0.62% d)

7. A bonding orbital for N2-N6 with 1.9940 electrons
__has 58.73% N 2 character in a p-pi orbital ( 99.76% p 0.24% d)
__has 41.27% N 6 character in a p-pi orbital ( 99.38% p 0.62% d)

11. A lone pair orbital for N6 with 1.9814 electrons

-With core pairs on: C 1 N 2 N 6 -

#### 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, 2, for C1-H3 with the third antibonding acceptor orbital, 90, for N2-N6 is 42.7 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-H4 with the second antibonding acceptor orbital, 89, for N2-N6 is 31.9 kJ/mol.

The interaction of bonding donor orbital, 4, for C1-H5 with the second antibonding acceptor orbital, 89, for N2-N6 is 32.1 kJ/mol.

The interaction of lone pair donor orbital, 11, for N6 with the antibonding acceptor orbital, 84, for C1-N2 is 51.0 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 ----- -4.421

14 ----- -5.355

13 ----- -10.13 12 ----- -10.13

11 -^-v- -17.35 10 -^-v- -17.36

9 -^-v- -18.56

8 -^-v- -20.52 7 -^-v- -20.53

6 -^-v- -21.55

5 -^-v- -28.67

4 -^-v- -36.49

3 -^-v- -275.5

2 -^-v- -388.4

1 -^-v- -389.3

## 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 = -149.1321213801 Hartrees