## CH2(+)CH2CH2OH, 3-dehydro-propanol cation (*see note)

 H5 H7 H8 \ | / H6 - C4 - C3 | | O1 - C2 / | \ H11 H10 H9
The ion charge is 1.

## Atomic Charges and Dipole Moment

O1 charge=-0.307
C2 charge= 0.033
C3 charge=-0.122
C4 charge= 0.037
H5 charge= 0.165
H6 charge= 0.138
H7 charge= 0.140
H8 charge= 0.127
H9 charge= 0.167
H10 charge= 0.139
H11 charge= 0.477
with a dipole moment of 4.34058 Debye

## Bond Lengths:

between O1 and C2: distance=1.562 ang___ between O1 and C3: distance=2.193 ang___
between O1 and C4: distance=1.563 ang___ between O1 and H11: distance=0.988 ang___
between C2 and C3: distance=1.541 ang___ between C2 and C4: distance=2.176 ang___
between C2 and H9: distance=1.098 ang___ between C2 and H10: distance=1.100 ang___
between C3 and C4: distance=1.541 ang___ between C3 and H7: distance=1.100 ang___
between C3 and H8: distance=1.100 ang___ between C4 and H5: distance=1.098 ang___
between C4 and H6: distance=1.100 ang___

## Bond Angles:

for C3-C2-O1: angle=89.92 deg___ for C4-C3-C2: angle=89.81 deg___
for H5-C4-C3: angle=118.9 deg___ for H6-C4-C3: angle=116.4 deg___
for H7-C3-C2: angle=113.3 deg___ for H8-C3-C2: angle=114.8 deg___
for H9-C2-O1: angle=106.7 deg___ for H10-C2-O1: angle=108.4 deg___
for H11-O1-C2: angle=115.5 deg___

## Bond Orders (Mulliken):

between O1 and C2: order=0.661___ between O1 and C3: order=-0.161___
between O1 and C4: order=0.660___ between O1 and H11: order=0.792___
between C2 and C3: order=0.852___ between C2 and C4: order=-0.082___
between C2 and H9: order=0.960___ between C2 and H10: order=0.948___
between C3 and C4: order=0.852___ between C3 and H7: order=0.963___
between C3 and H8: order=0.961___ between C4 and H5: order=0.960___
between C4 and H6: order=0.948___

## 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 O1-C2 with 1.9949 electrons
__has 75.99% O 1 character in a s0.96 p3 hybrid
__has 24.01% C 2 character in a s0.52 p3 hybrid

2. A bonding orbital for O1-C4 with 1.9948 electrons
__has 76.02% O 1 character in a s0.96 p3 hybrid
__has 23.98% C 4 character in a s0.52 p3 hybrid

3. A bonding orbital for O1-H11 with 1.9957 electrons
__has 77.74% O 1 character in a s0.97 p3 hybrid
__has 22.26% H11 character in a s orbital

4. A bonding orbital for C2-C3 with 1.9892 electrons
__has 50.87% C 2 character in a sp2.37 hybrid
__has 49.13% C 3 character in a s0.94 p3 hybrid

5. A bonding orbital for C2-H9 with 1.9936 electrons
__has 61.57% C 2 character in a sp2.53 hybrid
__has 38.43% H 9 character in a s orbital

6. A bonding orbital for C2-H10 with 1.9914 electrons
__has 60.57% C 2 character in a sp2.65 hybrid
__has 39.43% H10 character in a s orbital

7. A bonding orbital for C3-C4 with 1.9892 electrons
__has 49.12% C 3 character in a s0.94 p3 hybrid
__has 50.88% C 4 character in a sp2.37 hybrid

8. A bonding orbital for C3-H7 with 1.9903 electrons
__has 62.02% C 3 character in a sp2.83 hybrid
__has 37.98% H 7 character in a s orbital

9. A bonding orbital for C3-H8 with 1.9896 electrons
__has 62.04% C 3 character in a sp2.79 hybrid
__has 37.96% H 8 character in a s orbital

10. A bonding orbital for C4-H5 with 1.9936 electrons
__has 61.58% C 4 character in a sp2.52 hybrid
__has 38.42% H 5 character in a s orbital

11. A bonding orbital for C4-H6 with 1.9913 electrons
__has 60.57% C 4 character in a sp2.65 hybrid
__has 39.43% H 6 character in a s orbital

16. A lone pair orbital for O1 with 1.9876 electrons
__made from a sp2.73 hybrid

-With core pairs on: O 1 C 2 C 3 C 4 -

#### 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.

## 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 ----- -3.323

19 ----- -4.754

18 ----- -5.834

17 ----- -7.212

16 -^-v- -13.62

15 -^-v- -14.59

14 -^-v- -15.05

13 -^-v- -15.97

12 -^-v- -16.08

11 -^-v- -17.83

10 -^-v- -18.47

9 -^-v- -19.67

8 -^-v- -20.94

7 -^-v- -23.40

6 -^-v- -25.72

5 -^-v- -33.79

4 -^-v- -272.2

3 -^-v- -274.2 2 -^-v- -274.2

1 -^-v- -515.4

## 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 = -193.4940223064 Hartrees

* the linear cation is higher in energy.

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