## Acetone, CH3C=OCH3

 H5 H6 \ / C3 - H4 / O1 = C2 H9 \ / C7 - H8 / H10
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

O1 charge=-0.537
C2 charge= 0.788
C3 charge=-0.648
H4 charge= 0.171
H5 charge= 0.180
H6 charge= 0.171
C7 charge=-0.649
H8 charge= 0.171
H9 charge= 0.171
H10 charge= 0.180
with a dipole moment of 3.18893 Debye

## Bond Lengths:

between O1 and C2: distance=1.230 ang___ between O1 and C3: distance=2.408 ang___
between O1 and C7: distance=2.407 ang___ between C2 and C3: distance=1.523 ang___
between C2 and H5: distance=2.162 ang___ between C2 and C7: distance=1.523 ang___
between C2 and H10: distance=2.162 ang___ between C3 and H4: distance=1.106 ang___
between C3 and H5: distance=1.100 ang___ between C3 and H6: distance=1.106 ang___
between C3 and C7: distance=2.595 ang___ between C7 and H8: distance=1.106 ang___
between C7 and H9: distance=1.106 ang___ between C7 and H10: distance=1.100 ang___

## Bond Angles:

for C3-C2-O1: angle=121.6 deg___ for H4-C3-C2: angle=110.2 deg___
for H5-C3-C2: angle=109.9 deg___ for H6-C3-C2: angle=110.4 deg___
for C7-C2-O1: angle=121.5 deg___ for H8-C7-C2: angle=110.1 deg___
for H9-C7-C2: angle=110.4 deg___ for H10-C7-C2: angle=109.9 deg___

## Bond Orders (Mulliken):

between O1 and C2: order=1.986___ between O1 and C3: order=-0.080___
between O1 and C7: order=-0.080___ between C2 and C3: order=0.799___
between C2 and H5: order=-0.055___ between C2 and C7: order=0.799___
between C2 and H10: order=-0.055___ between C3 and H4: order=0.971___
between C3 and H5: order=0.998___ between C3 and H6: order=0.972___
between C3 and C7: order=-0.290___ between C7 and H8: order=0.971___
between C7 and H9: order=0.973___ between C7 and H10: order=0.998___

## 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 1.9975 electrons
__has 64.98% O 1 character in a sp1.44 hybrid
__has 35.02% C 2 character in a sp2.04 hybrid

2. A bonding orbital for O1-C2 with 1.9868 electrons
__has 70.26% O 1 character in a p-pi orbital ( 99.82% p 0.18% d)
__has 29.74% C 2 character in a p-pi orbital ( 99.41% p 0.59% d)

3. A bonding orbital for C2-C3 with 1.9931 electrons
__has 48.40% C 2 character in a sp1.96 hybrid
__has 51.60% C 3 character in a sp2.66 hybrid

4. A bonding orbital for C2-C7 with 1.9931 electrons
__has 48.40% C 2 character in a sp1.96 hybrid
__has 51.60% C 7 character in a sp2.66 hybrid

5. A bonding orbital for C3-H4 with 1.9808 electrons
__has 59.99% C 3 character in a s0.93 p3 hybrid
__has 40.01% H 4 character in a s orbital

6. A bonding orbital for C3-H5 with 1.9925 electrons
__has 60.92% C 3 character in a sp2.94 hybrid
__has 39.08% H 5 character in a s orbital

7. A bonding orbital for C3-H6 with 1.9812 electrons
__has 59.98% C 3 character in a s0.93 p3 hybrid
__has 40.02% H 6 character in a s orbital

8. A bonding orbital for C7-H8 with 1.9808 electrons
__has 59.99% C 7 character in a s0.93 p3 hybrid
__has 40.01% H 8 character in a s orbital

9. A bonding orbital for C7-H9 with 1.9813 electrons
__has 59.98% C 7 character in a s0.93 p3 hybrid
__has 40.02% H 9 character in a s orbital

10. A bonding orbital for C7-H10 with 1.9925 electrons
__has 60.92% C 7 character in a sp2.94 hybrid
__has 39.08% H10 character in a s orbital

15. A lone pair orbital for O1 with 1.9778 electrons

16. A lone pair orbital for O1 with 1.9168 electrons
__made from a p-pi orbital ( 99.93% p 0.07% d)

-With core pairs on: O 1 C 2 C 3 C 7 -

#### 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, 5, for C3-H4 with the second antibonding acceptor orbital, 124, for O1-C2 is 25.5 kJ/mol.

The interaction of bonding donor orbital, 7, for C3-H6 with the second antibonding acceptor orbital, 124, for O1-C2 is 24.7 kJ/mol.

The interaction of bonding donor orbital, 8, for C7-H8 with the second antibonding acceptor orbital, 124, for O1-C2 is 25.6 kJ/mol.

The interaction of bonding donor orbital, 9, for C7-H9 with the second antibonding acceptor orbital, 124, for O1-C2 is 24.6 kJ/mol.

The interaction of the second lone pair donor orbital, 16, for O1 with the antibonding acceptor orbital, 125, for C2-C3 is 108. kJ/mol.

The interaction of the second lone pair donor orbital, 16, for O1 with the antibonding acceptor orbital, 126, for C2-C7 is 107. 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.

20 ----- 2.158

19 ----- 1.894

18 ----- 1.293

17 ----- -1.886

16 -^-v- -5.777

15 -^-v- -8.687

14 -^-v- -9.237

13 -^-v- -9.627

12 -^-v- -9.868

11 -^-v- -11.02

10 -^-v- -11.33
9 -^-v- -11.42

8 -^-v- -13.05

7 -^-v- -17.48

6 -^-v- -18.99

5 -^-v- -25.76

4 -^-v- -266.5 3 -^-v- -266.5

2 -^-v- -268.9

1 -^-v- -506.2

## 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 = -193.2221765994 Hartrees