## CH3CH2CH=NH2+, propylimmonium cation

 H12 H3 \ / C1 = N2 / \ H11 H7 - C5 H4 \ / \ C8 - H9 H6 / H10
The ion charge is 1.

## Atomic Charges and Dipole Moment

C1 charge= 0.197
N2 charge=-0.512
H3 charge= 0.421
H4 charge= 0.417
C5 charge=-0.090
H6 charge= 0.121
H7 charge= 0.141
C8 charge=-0.313
H9 charge= 0.136
H10 charge= 0.161
H11 charge= 0.125
H12 charge= 0.193
with a dipole moment of 2.24638 Debye

## Bond Lengths:

between C1 and N2: distance=1.302 ang___ between C1 and C5: distance=1.471 ang___
between C1 and C8: distance=2.480 ang___ between C1 and H12: distance=1.101 ang___
between N2 and H3: distance=1.028 ang___ between N2 and H4: distance=1.029 ang___
between C5 and H6: distance=1.105 ang___ between C5 and H7: distance=1.110 ang___
between C5 and C8: distance=1.566 ang___ between C8 and H9: distance=1.102 ang___
between C8 and H10: distance=1.102 ang___ between C8 and H11: distance=1.103 ang___

## Bond Angles:

for H3-N2-C1: angle=122.0 deg___ for H4-N2-C1: angle=121.1 deg___
for C5-C1-N2: angle=124.2 deg___ for H6-C5-C1: angle=111.9 deg___
for H7-C5-C1: angle=107.4 deg___ for C8-C1-C5: angle=36.55 deg___
for H9-C8-C1: angle=93.81 deg___ for H10-C8-C1: angle=142.0 deg___
for H11-C8-C1: angle=92.32 deg___ for H12-C1-N2: angle=116.2 deg___

## Bond Orders (Mulliken):

between C1 and N2: order=1.442___ between C1 and C5: order=1.040___
between C1 and C8: order=-0.063___ between C1 and H12: order=0.919___
between N2 and H3: order=0.849___ between N2 and H4: order=0.854___
between C5 and H6: order=0.975___ between C5 and H7: order=0.923___
between C5 and C8: order=0.798___ between C8 and H9: order=0.939___
between C8 and H10: order=0.962___ between C8 and H11: order=0.991___

## 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 1.9969 electrons
__has 37.84% C 1 character in a sp2.07 hybrid
__has 62.16% N 2 character in a sp1.44 hybrid

2. A bonding orbital for C1-N2 with 1.9950 electrons
__has 23.14% C 1 character in a p-pi orbital ( 99.55% p 0.44% d)
__has 76.86% N 2 character in a p-pi orbital ( 99.92% p 0.07% d)

3. A bonding orbital for C1-C5 with 1.9888 electrons
__has 52.06% C 1 character in a sp1.63 hybrid
__has 47.94% C 5 character in a sp2.87 hybrid

4. A bonding orbital for C1-H12 with 1.9806 electrons
__has 61.18% C 1 character in a sp2.33 hybrid
__has 38.82% H12 character in a s orbital

5. A bonding orbital for N2-H3 with 1.9902 electrons
__has 72.73% N 2 character in a sp2.36 hybrid
__has 27.27% H 3 character in a s orbital

6. A bonding orbital for N2-H4 with 1.9902 electrons
__has 72.53% N 2 character in a sp2.38 hybrid
__has 27.47% H 4 character in a s orbital

7. A bonding orbital for C5-H6 with 1.9850 electrons
__has 61.27% C 5 character in a s0.97 p3 hybrid
__has 38.73% H 6 character in a s orbital

8. A bonding orbital for C5-H7 with 1.9598 electrons
__has 62.29% C 5 character in a s0.85 p3 hybrid
__has 37.71% H 7 character in a s orbital

9. A bonding orbital for C5-C8 with 1.9645 electrons
__has 54.62% C 5 character in a sp2.60 hybrid
__has 45.38% C 8 character in a sp2.84 hybrid

10. A bonding orbital for C8-H9 with 1.9932 electrons
__has 60.24% C 8 character in a s0.98 p3 hybrid
__has 39.76% H 9 character in a s orbital

11. A bonding orbital for C8-H10 with 1.9870 electrons
__has 61.55% C 8 character in a s0.97 p3 hybrid
__has 38.45% H10 character in a s orbital

12. A bonding orbital for C8-H11 with 1.9925 electrons
__has 60.35% C 8 character in a s0.99 p3 hybrid
__has 39.65% H11 character in a s orbital

-With core pairs on: C 1 N 2 C 5 C 8 -

#### 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, 4, for C1-H12 with the antibonding acceptor orbital, 138, for N2-H4 is 24.8 kJ/mol.

The interaction of bonding donor orbital, 8, for C5-H7 with the second antibonding acceptor orbital, 134, for C1-N2 is 41.4 kJ/mol.

The interaction of bonding donor orbital, 9, for C5-C8 with the second antibonding acceptor orbital, 134, for C1-N2 is 39.5 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.

20 ----- -2.876

19 ----- -4.015

18 ----- -4.677

17 ----- -8.684

16 -^-v- -13.40

15 -^-v- -13.68

14 -^-v- -14.17

13 -^-v- -15.45

12 -^-v- -15.68

11 -^-v- -16.58

10 -^-v- -18.29

9 -^-v- -19.92

8 -^-v- -20.82

7 -^-v- -22.29

6 -^-v- -24.97

5 -^-v- -30.31

4 -^-v- -271.0

3 -^-v- -272.1

2 -^-v- -274.8

1 -^-v- -385.4

## 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 = -173.6844668492 Hartrees

Note: CH3CH(NH2)CH2+, 2-aminopropyl cation, rearranges to give CH3CH2CH=NH2+, propylimmonium cation.