CH3CH2CH2+, propyl cation (see below)

H4
|
H5 - C3
/ |
H9 - C1 - C2
/ | | \
H10H8H7H6
The ion charge is 1.

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=-0.455
C2 charge=-0.016
C3 charge=-0.141
H4 charge= 0.210
H5 charge= 0.210
H6 charge= 0.200
H7 charge= 0.200
H8 charge= 0.247
H9 charge= 0.271
H10 charge= 0.271
with a dipole moment of 4.12030 Debye

Bond Lengths:

between C1 and C2: distance=1.807 ang___ between C1 and C3: distance=1.686 ang___
between C1 and H8: distance=1.123 ang___ between C1 and H9: distance=1.099 ang___
between C1 and H10: distance=1.099 ang___ between C2 and C3: distance=1.412 ang___
between C2 and H6: distance=1.097 ang___ between C2 and H7: distance=1.097 ang___
between C2 and H8: distance=1.881 ang___ between C3 and H4: distance=1.095 ang___
between C3 and H5: distance=1.095 ang___

Bond Angles:

for C3-C1-C2: angle=47.55 deg___ for H4-C3-C1: angle=109.3 deg___
for H5-C3-C1: angle=109.4 deg___ for H6-C2-C1: angle=108.3 deg___
for H7-C2-C1: angle=108.4 deg___ for H8-C1-C2: angle=75.89 deg___
for H9-C1-C2: angle=120.0 deg___ for H10-C1-C2: angle=120.0 deg___

Top of page.

Bond Orders (Mulliken):

between C1 and C2: order=0.327___ between C1 and C3: order=0.507___
between C1 and H8: order=0.824___ between C1 and H9: order=0.908___
between C1 and H10: order=0.908___ between C2 and C3: order=0.972___
between C2 and H6: order=0.940___ between C2 and H7: order=0.940___
between C2 and H8: order=0.076___ between C3 and H4: order=0.959___
between C3 and H5: order=0.959___

Top of page.

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-C3 with 1.6793 electrons
__has 54.21% C 1 character in a s0.93 p3 hybrid
__has 45.79% C 3 character in a s0.53 p3 hybrid

2. A bonding orbital for C1-H8 with 1.8389 electrons
__has 63.47% C 1 character in a sp2.07 hybrid
__has 36.53% H 8 character in a s orbital

3. A bonding orbital for C1-H9 with 1.9629 electrons
__has 63.67% C 1 character in a s0.84 p3 hybrid
__has 36.33% H 9 character in a s orbital

4. A bonding orbital for C1-H10 with 1.9627 electrons
__has 63.68% C 1 character in a s0.84 p3 hybrid
__has 36.32% H10 character in a s orbital

5. A bonding orbital for C2-C3 with 1.9936 electrons
__has 50.37% C 2 character in a sp2.11 hybrid
__has 49.63% C 3 character in a sp2.33 hybrid

6. A bonding orbital for C2-H6 with 1.9897 electrons
__has 62.95% C 2 character in a sp2.20 hybrid
__has 37.05% H 6 character in a s orbital

7. A bonding orbital for C2-H7 with 1.9897 electrons
__has 62.95% C 2 character in a sp2.20 hybrid
__has 37.05% H 7 character in a s orbital

8. A bonding orbital for C3-H4 with 1.9824 electrons
__has 63.12% C 3 character in a sp2.63 hybrid
__has 36.88% H 4 character in a s orbital

9. A bonding orbital for C3-H5 with 1.9824 electrons
__has 63.12% C 3 character in a sp2.63 hybrid
__has 36.88% H 5 character in a s orbital

13. A lone pair orbital for C2 with 0.5315 electrons
__made from a s0.18 p3 hybrid

-With core pairs on: C 1 C 2 C 3 -

Top of page.

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-C3 with the lone pair acceptor orbital, 13, for C2 is 910. kJ/mol.

The interaction of bonding donor orbital, 2, for C1-H8 with the lone pair acceptor orbital, 13, for C2 is 446. kJ/mol.

The interaction of bonding donor orbital, 5, for C2-C3 with the lone pair acceptor orbital, 13, for C2 is 67.7 kJ/mol.

The interaction of lone pair donor orbital, 13, for C2 with the antibonding acceptor orbital, 110, for C2-C3 is 23.3 kJ/mol.

Top of page.

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 ----- -3.803

15 ----- -4.236


14 ----- -5.442


13 ----- -8.267


12 -^-v- -15.23

11 -^-v- -15.41

10 -^-v- -16.23

9 -^-v- -16.51


8 -^-v- -17.85


7 -^-v- -18.93


6 -^-v- -21.52


5 -^-v- -22.63


4 -^-v- -27.85


3 -^-v- -273.7

2 -^-v- -273.9

1 -^-v- -274.5

Top of page.

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 = -118.2242143898 Hartrees

* Linear propyl cation rearranges easily to this cyclic cation or the isopropyl cation. The linear cation cannot be obtained by minimization procedures using DFT or ab initio theory. Top of page.

-> Return to Molecular Structure Page. -> Return to Chemistry Home Page