## vinyl alcohol, CH2CHOH

 H4 / O5 - C3 | \\ H1 C2 - H7 / H6
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= 0.443
C2 charge=-0.750
C3 charge= 0.199
H4 charge= 0.151
O5 charge=-0.547
H6 charge= 0.261
H7 charge= 0.242
with a dipole moment of 1.07427 Debye

## Bond Lengths:

between H1 and O5: distance=0.978 ang___ between C2 and C3: distance=1.344 ang___
between C2 and H6: distance=1.097 ang___ between C2 and H7: distance=1.092 ang___
between C3 and H4: distance=1.096 ang___ between C3 and O5: distance=1.377 ang___

## Bond Angles:

for C3-H1-C2: angle=32.11 deg___ for H4-H1-C2: angle=46.75 deg___
for O5-H1-C2: angle=74.52 deg___ for H6-C2-H1: angle=72.62 deg___
for H7-C2-H1: angle=169.7 deg___

## Bond Orders (Mulliken):

between H1 and O5: order=0.861___ between C2 and C3: order=1.896___
between C2 and H6: order=0.973___ between C2 and H7: order=0.976___
between C3 and H4: order=0.988___ between C3 and O5: order=0.899___

## 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 H1-O5 with 1.9897 electrons
__has 26.08% H 1 character in a s orbital
__has 73.92% O 5 character in a s0.80 p3 hybrid

2. A bonding orbital for C2-C3 with 1.9961 electrons
__has 49.17% C 2 character in a sp1.61 hybrid
__has 50.83% C 3 character in a sp1.31 hybrid

3. A bonding orbital for C2-C3 with 1.9965 electrons
__has 56.92% C 2 character in a p-pi orbital ( 99.86% p 0.14% d)
__has 43.08% C 3 character in a p-pi orbital ( 99.82% p 0.18% d)

4. A bonding orbital for C2-H6 with 1.9873 electrons
__has 59.16% C 2 character in a sp2.23 hybrid
__has 40.84% H 6 character in a s orbital

5. A bonding orbital for C2-H7 with 1.9834 electrons
__has 60.05% C 2 character in a sp2.22 hybrid
__has 39.95% H 7 character in a s orbital

6. A bonding orbital for C3-H4 with 1.9803 electrons
__has 58.91% C 3 character in a sp2.32 hybrid
__has 41.09% H 4 character in a s orbital

7. A bonding orbital for C3-O5 with 1.9965 electrons
__has 32.93% C 3 character in a sp2.70 hybrid
__has 67.07% O 5 character in a sp2.07 hybrid

11. A lone pair orbital for O5 with 1.9826 electrons

12. A lone pair orbital for O5 with 1.9144 electrons
__made from a p-pi orbital ( 99.95% p)

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

#### 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 C2-H6 with the antibonding acceptor orbital, 95, for C3-H4 is 23.6 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-H7 with the antibonding acceptor orbital, 96, for C3-O5 is 38.2 kJ/mol.

The interaction of bonding donor orbital, 6, for C3-H4 with the antibonding acceptor orbital, 93, for C2-H6 is 20.5 kJ/mol.

The interaction of lone pair donor orbital, 11, for O5 with the antibonding acceptor orbital, 91, for C2-C3 is 33.1 kJ/mol.

The interaction of the second lone pair donor orbital, 12, for O5 with the second antibonding acceptor orbital, 92, for C2-C3 is 165. 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.

16 ----- 2.606

15 ----- 1.987

14 ----- 0.651

13 ----- -0.677

12 -^-v- -5.813

11 -^-v- -8.913

10 -^-v- -9.368

9 -^-v- -9.535

8 -^-v- -11.79

7 -^-v- -12.26

6 -^-v- -15.41

5 -^-v- -18.43

4 -^-v- -26.35

3 -^-v- -266.0

2 -^-v- -267.9

1 -^-v- -507.4

## 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 = -153.8714273367 Hartrees