## N-dehydro-dimethylamine cation, CH3N(+)CH3 (see note)

 H3 / H9 N1 - C2 - H4 \ / \ C6 H5 / \ H8 H7
The ion charge is 1.

## Atomic Charges and Dipole Moment

N1 charge=-0.225
C2 charge= 0.132
H3 charge= 0.193
H4 charge= 0.193
H5 charge= 0.094
C6 charge= 0.123
H7 charge= 0.097
H8 charge= 0.196
H9 charge= 0.195
with a dipole moment of 3.39128 Debye

## Bond Lengths:

between N1 and C2: distance=1.375 ang___ between N1 and C6: distance=1.375 ang___
between C2 and H3: distance=1.132 ang___ between C2 and H4: distance=1.132 ang___
between C2 and H5: distance=1.105 ang___ between C6 and H7: distance=1.104 ang___
between C6 and H8: distance=1.133 ang___ between C6 and H9: distance=1.131 ang___

## Bond Angles:

for H3-C2-N1: angle=106.0 deg___ for H4-C2-N1: angle=105.5 deg___
for H5-C2-N1: angle=120.6 deg___ for C6-N1-C2: angle=119.9 deg___
for H7-C6-N1: angle=120.6 deg___ for H8-C6-N1: angle=105.4 deg___
for H9-C6-N1: angle=106.2 deg___

## Bond Orders (Mulliken):

between N1 and C2: order=0.998___ between N1 and C6: order=0.998___
between C2 and H3: order=0.848___ between C2 and H4: order=0.845___
between C2 and H5: order=0.961___ between C6 and H7: order=0.962___
between C6 and H8: order=0.843___ between C6 and H9: order=0.850___

## 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-C2 with 1.9927 electrons
__has 59.74% N 1 character in a sp1.95 hybrid
__has 40.26% C 2 character in a sp2.58 hybrid

2. A bonding orbital for N1-C6 with 1.9927 electrons
__has 59.74% N 1 character in a sp1.95 hybrid
__has 40.26% C 6 character in a sp2.58 hybrid

3. A bonding orbital for C2-H3 with 1.8895 electrons
__has 65.09% C 2 character in a s0.80 p3 hybrid
__has 34.91% H 3 character in a s orbital

4. A bonding orbital for C2-H4 with 1.8865 electrons
__has 65.08% C 2 character in a s0.80 p3 hybrid
__has 34.92% H 4 character in a s orbital

5. A bonding orbital for C2-H5 with 1.9979 electrons
__has 62.41% C 2 character in a sp2.30 hybrid
__has 37.59% H 5 character in a s orbital

6. A bonding orbital for C6-H7 with 1.9979 electrons
__has 62.40% C 6 character in a sp2.29 hybrid
__has 37.60% H 7 character in a s orbital

7. A bonding orbital for C6-H8 with 1.8851 electrons
__has 65.10% C 6 character in a s0.79 p3 hybrid
__has 34.90% H 8 character in a s orbital

8. A bonding orbital for C6-H9 with 1.8905 electrons
__has 65.08% C 6 character in a s0.81 p3 hybrid
__has 34.92% H 9 character in a s orbital

12. A lone pair orbital for N1 with 1.9517 electrons

13. A lone pair orbital for N1 with 0.4141 electrons
__made from a p-pi orbital ( 99.87% p 0.13% d)

-With core pairs on: N 1 C 2 C 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, 3, for C2-H3 with the second lone pair acceptor orbital, 13, for N1 is 129. kJ/mol.

The interaction of bonding donor orbital, 4, for C2-H4 with the second lone pair acceptor orbital, 13, for N1 is 135. kJ/mol.

The interaction of bonding donor orbital, 7, for C6-H8 with the second lone pair acceptor orbital, 13, for N1 is 137. kJ/mol.

The interaction of bonding donor orbital, 8, for C6-H9 with the second lone pair acceptor orbital, 13, for N1 is 127. kJ/mol.

The interaction of lone pair donor orbital, 12, for N1 with the antibonding acceptor orbital, 105, for C2-H5 is 40.9 kJ/mol.

The interaction of lone pair donor orbital, 12, for N1 with the antibonding acceptor orbital, 106, for C6-H7 is 40.8 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 ----- -3.341
15 ----- -3.354

14 ----- -4.317

13 ----- -11.70

12 -^-v- -13.21

11 -^-v- -15.96

10 -^-v- -16.23

9 -^-v- -18.13

8 -^-v- -18.47

7 -^-v- -18.61

6 -^-v- -21.36

5 -^-v- -25.12

4 -^-v- -30.41

3 -^-v- -273.9 2 -^-v- -273.9

1 -^-v- -386.3

## 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 = -134.2284042015 Hartrees

* This ion is higher in energy than N-methylmethaniminonium cation, CH3NH=CH2+, so this ion will most likely rearrange to the iminonium cation.