O-dehydro-acetic acid radical, CH3COO•

O3
//
O1 = C2
\
C4 - H7
/ |
H6H5
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

O1 charge=-0.355
C2 charge= 0.704
O3 charge=-0.355
C4 charge=-0.534
H5 charge= 0.180
H6 charge= 0.180
H7 charge= 0.179
with a dipole moment of 3.45428 Debye

Bond Lengths:

between O1 and C2: distance=1.277 ang___ between O1 and O3: distance=2.118 ang___
between C2 and O3: distance=1.277 ang___ between C2 and C4: distance=1.495 ang___
between C4 and H5: distance=1.105 ang___ between C4 and H6: distance=1.103 ang___
between C4 and H7: distance=1.103 ang___

Bond Angles:

for O3-C2-O1: angle=112.0 deg___ for C4-C2-O1: angle=123.9 deg___
for H5-C4-C2: angle=109.2 deg___ for H6-C4-C2: angle=110.0 deg___
for H7-C4-C2: angle=110.0 deg___

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Bond Orders (Mulliken):

between O1 and C2: order=1.564___ between O1 and O3: order=0.074___
between C2 and O3: order=1.564___ between C2 and C4: order=0.697___
between C4 and H5: order=0.957___ between C4 and H6: order=0.970___
between C4 and H7: 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 O1-C2 with 0.9988 electrons
__has 65.22% O 1 character in a sp2.01 hybrid
__has 34.78% C 2 character in a sp2.24 hybrid

2. A bonding orbital for C2-O3 with 0.9988 electrons
__has 34.78% C 2 character in a sp2.24 hybrid
__has 65.22% O 3 character in a sp2.01 hybrid

3. A bonding orbital for C2-C4 with 0.9985 electrons
__has 48.52% C 2 character in a sp1.58 hybrid
__has 51.48% C 4 character in a sp2.84 hybrid

4. A bonding orbital for C4-H5 with 0.9871 electrons
__has 62.37% C 4 character in a s0.96 p3 hybrid
__has 37.63% H 5 character in a s orbital

5. A bonding orbital for C4-H6 with 0.9931 electrons
__has 62.29% C 4 character in a s0.99 p3 hybrid
__has 37.71% H 6 character in a s orbital

6. A bonding orbital for C4-H7 with 0.9931 electrons
__has 62.29% C 4 character in a s0.99 p3 hybrid
__has 37.71% H 7 character in a s orbital

11. A lone pair orbital for O1 with 0.9918 electrons
__made from a sp0.49 hybrid

12. A lone pair orbital for O1 with 0.9727 electrons
__made from a p3 hybrid

13. A lone pair orbital for O1 with 0.8669 electrons
__made from a p-pi orbital ( 99.89% p 0.11% d)

14. A lone pair orbital for C2 with 0.2774 electrons
__made from a p-pi orbital ( 99.82% p 0.18% d)

15. A lone pair orbital for O3 with 0.9918 electrons
__made from a sp0.49 hybrid

16. A lone pair orbital for O3 with 0.9727 electrons
__made from a p3 hybrid

17. A lone pair orbital for O3 with 0.8668 electrons
__made from a p-pi orbital ( 99.89% p 0.11% d)

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

Up Electrons

1. A bonding orbital for O1-C2 with 0.9613 electrons
__has 59.65% O 1 character in a sp2.03 hybrid
__has 40.35% C 2 character in a sp2.68 hybrid

2. A antibonding orbital for O1-O3 with 0.9336 electrons
__has 50.01% O 1 character in a s0.14 p3 hybrid
__has 49.99% O 3 character in a s0.14 p3 hybrid

3. A bonding orbital for C2-O3 with 0.9613 electrons
__has 40.34% C 2 character in a sp2.68 hybrid
__has 59.66% O 3 character in a sp2.03 hybrid

4. A bonding orbital for C2-C4 with 0.9282 electrons
__has 58.23% C 2 character in a sp1.17 hybrid
__has 41.77% C 4 character in a s0.97 p3 hybrid

5. A bonding orbital for C4-H5 with 0.9848 electrons
__has 61.42% C 4 character in a s0.98 p3 hybrid
__has 38.58% H 5 character in a s orbital

6. A bonding orbital for C4-H6 with 0.9918 electrons
__has 61.13% C 4 character in a sp2.92 hybrid
__has 38.87% H 6 character in a s orbital

7. A bonding orbital for C4-H7 with 0.9918 electrons
__has 61.13% C 4 character in a sp2.92 hybrid
__has 38.87% H 7 character in a s orbital

12. A lone pair orbital for O1 with 0.9903 electrons
__made from a sp0.59 hybrid

13. A lone pair orbital for O1 with 0.8390 electrons
__made from a p-pi orbital ( 99.88% p 0.12% d)

14. A lone pair orbital for C2 with 0.3298 electrons
__made from a p-pi orbital ( 99.83% p 0.17% d)

15. A lone pair orbital for O3 with 0.9903 electrons
__made from a sp0.59 hybrid

16. A lone pair orbital for O3 with 0.8390 electrons
__made from a p-pi orbital ( 99.88% p 0.12% d)

109. A bonding orbital for O1-O3 with 0.1466 electrons
__has 49.99% O 1 character in a s0.14 p3 hybrid
__has 50.01% O 3 character in a s0.14 p3 hybrid

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

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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 bonding donor orbital, 1, for O1-C2 with the bonding acceptor orbital, 109, for O1-O3 is 110. kJ/mol.

The interaction of antibonding donor orbital, 2, for O1-O3 with the antibonding acceptor orbital, 108, for O1-C2 is 51.8 kJ/mol.

The interaction of antibonding donor orbital, 2, for O1-O3 with the antibonding acceptor orbital, 110, for C2-O3 is 51.7 kJ/mol.

The interaction of bonding donor orbital, 3, for C2-O3 with the bonding acceptor orbital, 109, for O1-O3 is 110. kJ/mol.

The interaction of bonding donor orbital, 4, for C2-C4 with the bonding acceptor orbital, 109, for O1-O3 is 62.9 kJ/mol.

The interaction of bonding donor orbital, 5, for C4-H5 with the lone pair acceptor orbital, 14, for C2 is 20.5 kJ/mol.

The interaction of the second lone pair donor orbital, 13, for O1 with the lone pair acceptor orbital, 14, for C2 is 457. kJ/mol.

The interaction of the second lone pair donor orbital, 16, for O3 with the lone pair acceptor orbital, 14, for C2 is 457. 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 ----- 2.707

19 ----- 2.101

18 ----- 1.385


17 ----- -1.922


16 -^--- -7.978

15 -^-v- -8.208

14 -^-v- -8.635


13 -^-v- -10.26

12 -^-v- -10.62


11 -^-v- -12.24
10 -^-v- -12.30

9 -^-v- -12.70


8 -^-v- -13.92


7 -^-v- -19.26


6 -^-v- -25.33


5 -^-v- -28.28


4 -^-v- -267.3


3 -^-v- -270.5


2 -^-v- -508.2 1 -^-v- -508.2

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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 = -228.5089228629 Hartrees

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