## vinyl alcohol radical cation, CH2CHOH+• (see note)

 H4 \ H7 C3 - H5 \ // O1 - C2 \ H6
The ion charge is 1. The multiplicity is 2.

## Atomic Charges and Dipole Moment

O1 charge=-0.285
C2 charge= 0.323
C3 charge=-0.156
H4 charge= 0.226
H5 charge= 0.228
H6 charge= 0.187
H7 charge= 0.474
with a dipole moment of 7.29022 Debye

## Bond Lengths:

between O1 and C2: distance=1.305 ang___ between O1 and H7: distance=0.992 ang___
between C2 and C3: distance=1.416 ang___ between C2 and H6: distance=1.100 ang___
between C3 and H4: distance=1.100 ang___ between C3 and H5: distance=1.097 ang___

## Bond Angles:

for C3-C2-O1: angle=124.5 deg___ for H4-C3-C2: angle=122.2 deg___
for H5-C3-C2: angle=118.9 deg___ for H6-C2-O1: angle=113.1 deg___
for H7-O1-C2: angle=114.9 deg___

## Bond Orders (Mulliken):

between O1 and C2: order=1.383___ between O1 and H7: order=0.803___
between C2 and C3: order=1.250___ between C2 and H6: order=0.921___
between C3 and H4: order=0.926___ between C3 and H5: order=0.940___

## 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 O1-C2 with 0.9990 electrons
__has 67.34% O 1 character in a sp1.87 hybrid
__has 32.66% C 2 character in a sp2.40 hybrid

2. A bonding orbital for O1-H7 with 0.9944 electrons
__has 77.76% O 1 character in a s0.89 p3 hybrid
__has 22.24% H 7 character in a s orbital

3. A bonding orbital for C2-C3 with 0.9990 electrons
__has 29.27% C 2 character in a p-pi orbital ( 99.59% p 0.41% d)
__has 70.73% C 3 character in a p-pi orbital ( 99.83% p 0.17% d)

4. A bonding orbital for C2-C3 with 0.9981 electrons
__has 51.05% C 2 character in a sp1.62 hybrid
__has 48.95% C 3 character in a sp1.91 hybrid

5. A bonding orbital for C2-H6 with 0.9927 electrons
__has 62.29% C 2 character in a sp2.04 hybrid
__has 37.71% H 6 character in a s orbital

6. A bonding orbital for C3-H4 with 0.9950 electrons
__has 62.97% C 3 character in a sp2.01 hybrid
__has 37.03% H 4 character in a s orbital

7. A bonding orbital for C3-H5 with 0.9936 electrons
__has 63.76% C 3 character in a sp2.05 hybrid
__has 36.24% H 5 character in a s orbital

11. A lone pair orbital for O1 with 0.9895 electrons

12. A lone pair orbital for O1 with 0.9286 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)

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

#### Up Electrons

1. A bonding orbital for O1-C2 with 0.9990 electrons
__has 66.49% O 1 character in a sp1.82 hybrid
__has 33.51% C 2 character in a sp2.39 hybrid

2. A bonding orbital for O1-C2 with 0.9898 electrons
__has 78.00% O 1 character in a p-pi orbital ( 99.87% p 0.12% d)
__has 22.00% C 2 character in a p-pi orbital ( 99.30% p 0.70% d)

3. A bonding orbital for O1-H7 with 0.9944 electrons
__has 76.81% O 1 character in a s0.90 p3 hybrid
__has 23.19% H 7 character in a s orbital

4. A bonding orbital for C2-C3 with 0.9983 electrons
__has 53.49% C 2 character in a sp1.59 hybrid
__has 46.51% C 3 character in a sp1.92 hybrid

5. A bonding orbital for C2-H6 with 0.9927 electrons
__has 61.79% C 2 character in a sp2.09 hybrid
__has 38.21% H 6 character in a s orbital

6. A bonding orbital for C3-H4 with 0.9958 electrons
__has 59.13% C 3 character in a sp2.01 hybrid
__has 40.87% H 4 character in a s orbital

7. A bonding orbital for C3-H5 with 0.9945 electrons
__has 59.88% C 3 character in a sp2.05 hybrid
__has 40.12% H 5 character in a s orbital

11. A lone pair orbital for O1 with 0.9895 electrons

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

#### 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. Only the spin up electron orbital energies are given.

16 ----- -3.546

15 ----- -4.029

14 ----- -5.810

13 ----- -8.928

12 -^--- -14.00

11 -^-v- -16.25

10 -^-v- -17.05

9 -^-v- -18.16

8 -^-v- -19.54

7 -^-v- -20.07

6 -^-v- -23.61

5 -^-v- -26.39

4 -^-v- -35.05

3 -^-v- -275.0

2 -^-v- -276.5

1 -^-v- -516.0

## 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 = -153.5337247299 Hartrees

Note: This ion results from the McLafferty rearrangment of aldehydes. It is the enol radical cation of acetaldehyde, or the vinyl alcohol radical cation.