CH3CH2CH2OH+•, propanol radical cation

H9H10O5 - H6
\ | /
C3 - C4 - H12
/ \
H1 - C2H11
| \
H8H7
The ion charge is 1. The multiplicity is 2.

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

H1 charge= 0.218
C2 charge=-0.563
C3 charge= 0.040
C4 charge= 0.136
O5 charge=-0.374
H6 charge= 0.481
H7 charge= 0.202
H8 charge= 0.200
H9 charge= 0.161
H10 charge= 0.158
H11 charge= 0.166
H12 charge= 0.171
with a dipole moment of 15.51929 Debye

Bond Lengths:

between H1 and C2: distance=1.100 ang___ between C2 and C3: distance=1.522 ang___
between C2 and H7: distance=1.109 ang___ between C2 and H8: distance=1.108 ang___
between C3 and C4: distance=1.496 ang___ between C3 and O5: distance=2.437 ang___
between C3 and H9: distance=1.126 ang___ between C3 and H10: distance=1.124 ang___
between C4 and O5: distance=1.392 ang___ between C4 and H11: distance=1.137 ang___
between C4 and H12: distance=1.140 ang___ between O5 and H6: distance=0.988 ang___

Bond Angles:

for C3-C2-H1: angle=109.9 deg___ for C4-C3-C2: angle=117.0 deg___
for O5-C4-C3: angle=115.0 deg___ for H6-O5-C4: angle=111.9 deg___
for H7-C2-H1: angle=107.3 deg___ for H8-C2-H1: angle=107.7 deg___
for H9-C3-C2: angle=110.5 deg___ for H10-C3-C2: angle=110.7 deg___
for H11-C4-C3: angle=112.9 deg___ for H12-C4-C3: angle=112.2 deg___

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Bond Orders (Mulliken):

between H1 and C2: order=0.971___ between C2 and C3: order=0.851___
between C2 and H7: order=0.969___ between C2 and H8: order=0.967___
between C3 and C4: order=0.824___ between C3 and O5: order=-0.083___
between C3 and H9: order=0.958___ between C3 and H10: order=0.953___
between C4 and O5: order=0.843___ between C4 and H11: order=0.909___
between C4 and H12: order=0.897___ between O5 and H6: order=0.777___

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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. The Lewis structure is built for the up and down electrons, separately. Note that the up and down structures can be very different.

Hybridization in the Best Lewis Structure

Down Electrons

1. A bonding orbital for H1-C2 with 0.9935 electrons
__has 38.47% H 1 character in a s orbital
__has 61.53% C 2 character in a s0.98 p3 hybrid

2. A bonding orbital for C2-C3 with 0.9929 electrons
__has 46.21% C 2 character in a sp2.55 hybrid
__has 53.79% C 3 character in a sp2.14 hybrid

3. A bonding orbital for C2-H7 with 0.9955 electrons
__has 60.05% C 2 character in a s0.92 p3 hybrid
__has 39.95% H 7 character in a s orbital

4. A bonding orbital for C2-H8 with 0.9955 electrons
__has 60.06% C 2 character in a s0.93 p3 hybrid
__has 39.94% H 8 character in a s orbital

5. A bonding orbital for C3-C4 with 0.9966 electrons
__has 45.91% C 3 character in a sp2.78 hybrid
__has 54.09% C 4 character in a sp1.81 hybrid

6. A bonding orbital for C3-H9 with 0.9890 electrons
__has 60.83% C 3 character in a s0.79 p3 hybrid
__has 39.17% H 9 character in a s orbital

7. A bonding orbital for C3-H10 with 0.9892 electrons
__has 60.93% C 3 character in a s0.80 p3 hybrid
__has 39.07% H10 character in a s orbital

8. A bonding orbital for C4-O5 with 0.9985 electrons
__has 27.22% C 4 character in a s0.80 p3 hybrid
__has 72.78% O 5 character in a sp1.86 hybrid

9. A bonding orbital for C4-H11 with 0.9949 electrons
__has 59.70% C 4 character in a s0.85 p3 hybrid
__has 40.30% H11 character in a s orbital

10. A bonding orbital for C4-H12 with 0.9949 electrons
__has 59.53% C 4 character in a s0.83 p3 hybrid
__has 40.47% H12 character in a s orbital

11. A bonding orbital for O5-H6 with 0.9956 electrons
__has 78.77% O 5 character in a s0.77 p3 hybrid
__has 21.23% H 6 character in a s orbital

16. A lone pair orbital for O5 with 0.9952 electrons
__made from a sp1.23 hybrid

17. A lone pair orbital for O5 with 0.9909 electrons
__made from a p-pi orbital ( 99.95% p)

-With core pairs on: C 2 C 3 C 4 O 5 -

Up Electrons

1. A bonding orbital for H1-C2 with 0.9937 electrons
__has 38.50% H 1 character in a s orbital
__has 61.50% C 2 character in a s0.98 p3 hybrid

2. A bonding orbital for C2-C3 with 0.9935 electrons
__has 46.33% C 2 character in a sp2.54 hybrid
__has 53.67% C 3 character in a sp2.14 hybrid

3. A bonding orbital for C2-H7 with 0.9954 electrons
__has 60.04% C 2 character in a s0.92 p3 hybrid
__has 39.96% H 7 character in a s orbital

4. A bonding orbital for C2-H8 with 0.9954 electrons
__has 60.05% C 2 character in a s0.93 p3 hybrid
__has 39.95% H 8 character in a s orbital

5. A bonding orbital for C3-C4 with 0.9963 electrons
__has 45.77% C 3 character in a sp2.78 hybrid
__has 54.23% C 4 character in a sp1.83 hybrid

6. A bonding orbital for C3-H9 with 0.9893 electrons
__has 60.93% C 3 character in a s0.79 p3 hybrid
__has 39.07% H 9 character in a s orbital

7. A bonding orbital for C3-H10 with 0.9896 electrons
__has 61.01% C 3 character in a s0.80 p3 hybrid
__has 38.99% H10 character in a s orbital

8. A bonding orbital for C4-O5 with 0.9983 electrons
__has 31.55% C 4 character in a s0.81 p3 hybrid
__has 68.45% O 5 character in a sp1.77 hybrid

9. A bonding orbital for C4-H11 with 0.9386 electrons
__has 65.69% C 4 character in a s0.85 p3 hybrid
__has 34.31% H11 character in a s orbital

10. A bonding orbital for C4-H12 with 0.9334 electrons
__has 66.02% C 4 character in a s0.83 p3 hybrid
__has 33.98% H12 character in a s orbital

11. A bonding orbital for O5-H6 with 0.9957 electrons
__has 74.93% O 5 character in a s0.84 p3 hybrid
__has 25.07% H 6 character in a s orbital

16. A lone pair orbital for O5 with 0.9945 electrons
__made from a sp1.37 hybrid

17. A lone pair orbital for O5 with 0.1200 electrons
__made from a p-pi orbital ( 99.78% p 0.22% d)

-With core pairs on: C 2 C 3 C 4 O 5 -

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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, 9, for C4-H11 with the second lone pair acceptor orbital, 17, for O5 is 66.8 kJ/mol.

The interaction of bonding donor orbital, 10, for C4-H12 with the second lone pair acceptor orbital, 17, for O5 is 74.7 kJ/mol.

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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. Only the spin up electron orbital energies are given.

21 ----- -3.168

20 ----- -3.408

19 ----- -3.881


18 ----- -5.482


17 -^--- -13.45

16 -^-v- -13.96
15 -^-v- -14.02

14 -^-v- -14.99

13 -^-v- -15.37

12 -^-v- -15.98


11 -^-v- -17.36


10 -^-v- -18.47


9 -^-v- -20.16

8 -^-v- -20.80


7 -^-v- -22.96


6 -^-v- -25.69


5 -^-v- -33.33


4 -^-v- -271.3


3 -^-v- -272.6


2 -^-v- -274.8


1 -^-v- -514.8

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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 = -194.0574595907 Hartrees

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