HOOCCH2•, dehydroacetic acid radical

O3
//
O1 - C2
| \
H7C4 - H6
/
H5
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=-0.582
C2 charge= 0.750
O3 charge=-0.474
C4 charge=-0.537
H5 charge= 0.206
H6 charge= 0.227
H7 charge= 0.409
with a dipole moment of 4.61103 Debye

Bond Lengths:

between O1 and C2: distance=1.386 ang___ between O1 and O3: distance=2.258 ang___
between O1 and C4: distance=2.430 ang___ between O1 and H7: distance=0.978 ang___
between C2 and O3: distance=1.232 ang___ between C2 and C4: distance=1.453 ang___
between C4 and H5: distance=1.096 ang___ between C4 and H6: distance=1.093 ang___

Bond Angles:

for O3-C2-O1: angle=119.0 deg___ for C4-C2-O1: angle=117.6 deg___
for H5-C4-C2: angle=123.3 deg___ for H6-C4-C2: angle=117.5 deg___
for H7-O1-C2: angle=110.2 deg___

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Bond Orders (Mulliken):

between O1 and C2: order=1.020___ between O1 and O3: order=-0.184___
between O1 and C4: order=-0.076___ between O1 and H7: order=0.840___
between C2 and O3: order=1.837___ between C2 and C4: order=1.014___
between C4 and H5: order=0.953___ between C4 and H6: order=0.958___

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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. 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 0.9981 electrons
__has 67.16% O 1 character in a sp2.30 hybrid
__has 32.84% C 2 character in a sp2.49 hybrid

2. A bonding orbital for O1-H7 with 0.9939 electrons
__has 73.80% O 1 character in a s0.85 p3 hybrid
__has 26.20% H 7 character in a s orbital

3. A bonding orbital for C2-O3 with 0.9993 electrons
__has 14.04% C 2 character in a p3 hybrid
__has 85.96% O 3 character in a p3 hybrid

4. A bonding orbital for C2-O3 with 0.9986 electrons
__has 34.91% C 2 character in a sp1.86 hybrid
__has 65.09% O 3 character in a sp1.65 hybrid

5. A bonding orbital for C2-C4 with 0.9973 electrons
__has 48.20% C 2 character in a sp1.73 hybrid
__has 51.80% C 4 character in a sp1.90 hybrid

6. A bonding orbital for C4-H5 with 0.9952 electrons
__has 60.78% C 4 character in a sp2.04 hybrid
__has 39.22% H 5 character in a s orbital

7. A bonding orbital for C4-H6 with 0.9945 electrons
__has 62.04% C 4 character in a sp2.05 hybrid
__has 37.96% H 6 character in a s orbital

12. A lone pair orbital for O1 with 0.9910 electrons
__made from a sp1.09 hybrid

13. A lone pair orbital for O1 with 0.9427 electrons
__made from a p-pi orbital ( 99.93% p 0.07% d)

14. A lone pair orbital for O3 with 0.9906 electrons
__made from a sp0.60 hybrid

15. A lone pair orbital for O3 with 0.9488 electrons
__made from a p3 hybrid

16. A lone pair orbital for C4 with 0.9028 electrons
__made from a p3 hybrid

110. A antibonding orbital for C2-O3 with 0.1479 electrons
__has 85.96% C 2 character in a p3 hybrid
__has 14.04% O 3 character in a p3 hybrid

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

Up Electrons

1. A bonding orbital for O1-C2 with 0.9981 electrons
__has 66.63% O 1 character in a sp2.36 hybrid
__has 33.37% C 2 character in a sp2.64 hybrid

2. A bonding orbital for O1-H7 with 0.9939 electrons
__has 73.90% O 1 character in a s0.85 p3 hybrid
__has 26.10% H 7 character in a s orbital

3. A bonding orbital for C2-O3 with 0.9985 electrons
__has 37.66% C 2 character in a sp1.88 hybrid
__has 62.34% O 3 character in a sp1.62 hybrid

4. A bonding orbital for C2-O3 with 0.9618 electrons
__has 51.30% C 2 character in a p3 hybrid
__has 48.70% O 3 character in a p3 hybrid

5. A bonding orbital for C2-C4 with 0.9973 electrons
__has 53.37% C 2 character in a sp1.62 hybrid
__has 46.63% C 4 character in a sp1.94 hybrid

6. A bonding orbital for C4-H5 with 0.9963 electrons
__has 55.71% C 4 character in a sp2.03 hybrid
__has 44.29% H 5 character in a s orbital

7. A bonding orbital for C4-H6 with 0.9953 electrons
__has 57.10% C 4 character in a sp2.03 hybrid
__has 42.90% H 6 character in a s orbital

12. A lone pair orbital for O1 with 0.9918 electrons
__made from a sp1.07 hybrid

13. A lone pair orbital for O1 with 0.9620 electrons
__made from a p3 hybrid

14. A lone pair orbital for O3 with 0.9900 electrons
__made from a sp0.61 hybrid

15. A lone pair orbital for O3 with 0.9437 electrons
__made from a 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 the second bonding donor orbital, 4, for C2-O3 with the lone pair acceptor orbital, 16, for C4 is 65.8 kJ/mol.

The interaction of the second lone pair donor orbital, 13, for O1 with the second antibonding acceptor orbital, 111, for C2-O3 is 69.5 kJ/mol.

The interaction of the second lone pair donor orbital, 15, for O3 with the antibonding acceptor orbital, 108, for O1-C2 is 89.5 kJ/mol.

The interaction of the second lone pair donor orbital, 15, for O3 with the antibonding acceptor orbital, 112, for C2-C4 is 42.3 kJ/mol.

The interaction of lone pair donor orbital, 16, for C4 with the second antibonding acceptor orbital, 111, for C2-O3 is 27.8 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 ----- 2.360

19 ----- 1.669

18 ----- 0.005

17 ----- -0.784


16 -^--- -6.611

15 -^-v- -6.906


14 -^-v- -8.138


13 -^-v- -9.571


12 -^-v- -10.68

11 -^-v- -11.31

10 -^-v- -12.08


9 -^-v- -13.33


8 -^-v- -15.55


7 -^-v- -18.97


6 -^-v- -25.48


5 -^-v- -27.48


4 -^-v- -268.1


3 -^-v- -270.1


2 -^-v- -506.5


1 -^-v- -507.9

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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 = -228.5048296372 Hartrees

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