dehydro-2-propanone radical, CH3C=OCH2

O5H3
\\ /
C1 - C2
/ \
H7 - C6H4
| \
H9H8
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

C1 charge= 0.707
C2 charge=-0.486
H3 charge= 0.200
H4 charge= 0.192
O5 charge=-0.515
C6 charge=-0.564
H7 charge= 0.164
H8 charge= 0.147
H9 charge= 0.153
with a dipole moment of 3.25470 Debye

Bond Lengths:

between C1 and C2: distance=1.444 ang___ between C1 and O5: distance=1.256 ang___
between C1 and C6: distance=1.525 ang___ between C1 and H7: distance=2.158 ang___
between C2 and H3: distance=1.095 ang___ between C2 and H4: distance=1.096 ang___
between C2 and O5: distance=2.342 ang___ between C2 and C6: distance=2.553 ang___
between O5 and C6: distance=2.427 ang___ between C6 and H7: distance=1.100 ang___
between C6 and H8: distance=1.105 ang___ between C6 and H9: distance=1.106 ang___

Bond Angles:

for H3-C2-C1: angle=118.4 deg___ for H4-C2-C1: angle=122.0 deg___
for O5-C1-C2: angle=120.1 deg___ for C6-C1-C2: angle=118.5 deg___
for H7-C6-C1: angle=109.4 deg___ for H8-C6-C1: angle=111.1 deg___
for H9-C6-C1: angle=110.0 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=1.085___ between C1 and O5: order=1.625___
between C1 and C6: order=0.796___ between C1 and H7: order=-0.058___
between C2 and H3: order=0.958___ between C2 and H4: order=0.937___
between C2 and O5: order=-0.067___ between C2 and C6: order=-0.186___
between O5 and C6: order=-0.089___ between C6 and H7: order=1.011___
between C6 and H8: order=0.981___ between C6 and H9: order=0.970___

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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. Please note that your structure can't be well described by a single Lewis structure, because of extensive delocalization.

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 C1-C2 with 0.9975 electrons
__has 48.09% C 1 character in a sp1.93 hybrid
__has 51.91% C 2 character in a sp1.74 hybrid

2. A bonding orbital for C1-O5 with 0.9988 electrons
__has 33.91% C 1 character in a sp2.14 hybrid
__has 66.09% O 5 character in a sp1.61 hybrid

3. A bonding orbital for C1-C6 with 0.9968 electrons
__has 48.27% C 1 character in a sp1.91 hybrid
__has 51.73% C 6 character in a sp2.65 hybrid

4. A bonding orbital for C2-H3 with 0.9951 electrons
__has 61.36% C 2 character in a sp2.14 hybrid
__has 38.64% H 3 character in a s orbital

5. A bonding orbital for C2-H4 with 0.9951 electrons
__has 60.61% C 2 character in a sp2.13 hybrid
__has 39.39% H 4 character in a s orbital

6. A bonding orbital for C6-H7 with 0.9960 electrons
__has 60.80% C 6 character in a s0.99 p3 hybrid
__has 39.20% H 7 character in a s orbital

7. A bonding orbital for C6-H8 with 0.9918 electrons
__has 60.31% C 6 character in a s0.95 p3 hybrid
__has 39.69% H 8 character in a s orbital

8. A bonding orbital for C6-H9 with 0.9898 electrons
__has 60.57% C 6 character in a s0.93 p3 hybrid
__has 39.43% H 9 character in a s orbital

13. A lone pair orbital for C1 with 0.2357 electrons
__made from a p-pi orbital ( 99.90% p 0.10% d)

14. A lone pair orbital for C2 with 0.8750 electrons
__made from a p3 hybrid

15. A lone pair orbital for O5 with 0.9912 electrons
__made from a sp0.61 hybrid

16. A lone pair orbital for O5 with 0.9657 electrons
__made from a p-pi orbital ( 99.93% p 0.06% d)

17. A lone pair orbital for O5 with 0.8997 electrons
__made from a p-pi orbital ( 99.90% p 0.10% d)

-With core pairs on: C 1 C 2 O 5 C 6 -

Up Electrons

1. A bonding orbital for C1-C2 with 0.9970 electrons
__has 53.42% C 1 character in a sp1.83 hybrid
__has 46.58% C 2 character in a sp1.80 hybrid

2. A bonding orbital for C1-O5 with 0.9985 electrons
__has 37.61% C 1 character in a sp2.18 hybrid
__has 62.39% O 5 character in a sp1.58 hybrid

3. A bonding orbital for C1-O5 with 0.9427 electrons
__has 62.53% C 1 character in a p-pi orbital ( 99.81% p 0.19% d)
__has 37.47% O 5 character in a p-pi orbital ( 99.76% p 0.24% d)

4. A bonding orbital for C1-C6 with 0.9965 electrons
__has 50.30% C 1 character in a sp1.97 hybrid
__has 49.70% C 6 character in a sp2.70 hybrid

5. A bonding orbital for C2-H3 with 0.9959 electrons
__has 56.69% C 2 character in a sp2.10 hybrid
__has 43.31% H 3 character in a s orbital

6. A bonding orbital for C2-H4 with 0.9959 electrons
__has 55.85% C 2 character in a sp2.10 hybrid
__has 44.15% H 4 character in a s orbital

7. A bonding orbital for C6-H7 with 0.9965 electrons
__has 60.49% C 6 character in a sp2.99 hybrid
__has 39.51% H 7 character in a s orbital

8. A bonding orbital for C6-H8 with 0.9941 electrons
__has 59.27% C 6 character in a s0.96 p3 hybrid
__has 40.73% H 8 character in a s orbital

9. A bonding orbital for C6-H9 with 0.9934 electrons
__has 59.29% C 6 character in a s0.94 p3 hybrid
__has 40.71% H 9 character in a s orbital

15. A lone pair orbital for O5 with 0.9902 electrons
__made from a sp0.62 hybrid

16. A lone pair orbital for O5 with 0.9635 electrons
__made from a p3 hybrid

-With core pairs on: C 1 C 2 O 5 C 6 -

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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 the second bonding donor orbital, 3, for C1-O5 with the lone pair acceptor orbital, 14, for C2 is 94.6 kJ/mol.

The interaction of the second lone pair donor orbital, 16, for O5 with the antibonding acceptor orbital, 118, for C1-C2 is 41.7 kJ/mol.

The interaction of the second lone pair donor orbital, 16, for O5 with the antibonding acceptor orbital, 121, for C1-C6 is 50.8 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.

20 ----- 2.238

19 ----- 1.815

18 ----- 1.544


17 ----- -1.227


16 -^--- -6.048

15 -^-v- -6.315


14 -^-v- -9.164

13 -^-v- -9.535

12 -^-v- -9.837


11 -^-v- -11.06

10 -^-v- -11.35

9 -^-v- -11.79


8 -^-v- -13.34


7 -^-v- -17.50


6 -^-v- -19.17


5 -^-v- -25.68


4 -^-v- -266.5


3 -^-v- -267.6


2 -^-v- -268.7


1 -^-v- -506.3

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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 = -192.5611869911 Hartrees

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