CH3OOCCH2•, methyl-dehydro-acetate radical

O3
//
O1 - C2
/ \
H8 - C7C4 - H6
| \ /
H10H9H5
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=-0.379
C2 charge= 0.753
O3 charge=-0.514
C4 charge=-0.431
H5 charge= 0.173
H6 charge= 0.186
C7 charge=-0.068
H8 charge= 0.126
H9 charge= 0.073
H10 charge= 0.080
with a dipole moment of 4.70013 Debye

Bond Lengths:

between O1 and C2: distance=1.378 ang___ between O1 and O3: distance=2.241 ang___
between O1 and C4: distance=2.453 ang___ between O1 and C7: distance=1.448 ang___
between C2 and O3: distance=1.239 ang___ between C2 and C4: distance=1.449 ang___
between C4 and H5: distance=1.094 ang___ between C4 and H6: distance=1.093 ang___
between C7 and H8: distance=1.100 ang___ between C7 and H9: distance=1.105 ang___
between C7 and H10: distance=1.106 ang___

Bond Angles:

for O3-C2-O1: angle=117.7 deg___ for C4-C2-O1: angle=120.3 deg___
for H5-C4-C2: angle=123.9 deg___ for H6-C4-C2: angle=116.5 deg___
for C7-O1-C2: angle=119.5 deg___ for H8-C7-O1: angle=105.4 deg___
for H9-C7-O1: angle=111.3 deg___ for H10-C7-O1: angle=111.1 deg___

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Bond Orders (Mulliken):

between O1 and C2: order=0.938___ between O1 and O3: order=-0.183___
between O1 and C4: order=-0.096___ between O1 and C7: order=0.710___
between C2 and O3: order=1.804___ between C2 and C4: order=1.060___
between C4 and H5: order=0.958___ between C4 and H6: order=0.945___
between C7 and H8: order=0.993___ between C7 and H9: order=0.973___
between C7 and H10: order=0.969___

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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 0.9967 electrons
__has 67.49% O 1 character in a sp2.32 hybrid
__has 32.51% C 2 character in a sp2.47 hybrid

2. A bonding orbital for O1-C7 with 0.9954 electrons
__has 68.19% O 1 character in a sp2.42 hybrid
__has 31.81% C 7 character in a s0.85 p3 hybrid

3. A bonding orbital for C2-O3 with 0.9981 electrons
__has 34.86% C 2 character in a sp1.90 hybrid
__has 65.14% O 3 character in a sp1.68 hybrid

4. A bonding orbital for C2-C4 with 0.9974 electrons
__has 48.23% C 2 character in a sp1.70 hybrid
__has 51.77% C 4 character in a sp1.90 hybrid

5. A bonding orbital for C4-H5 with 0.9946 electrons
__has 61.13% C 4 character in a sp2.02 hybrid
__has 38.87% H 5 character in a s orbital

6. A bonding orbital for C4-H6 with 0.9945 electrons
__has 61.91% C 4 character in a sp2.07 hybrid
__has 38.09% H 6 character in a s orbital

7. A bonding orbital for C7-H8 with 0.9966 electrons
__has 59.44% C 7 character in a sp2.86 hybrid
__has 40.56% H 8 character in a s orbital

8. A bonding orbital for C7-H9 with 0.9977 electrons
__has 58.29% C 7 character in a sp2.83 hybrid
__has 41.71% H 9 character in a s orbital

9. A bonding orbital for C7-H10 with 0.9977 electrons
__has 58.18% C 7 character in a sp2.83 hybrid
__has 41.82% H10 character in a s orbital

15. A lone pair orbital for O1 with 0.9837 electrons
__made from a sp1.44 hybrid

16. A lone pair orbital for O1 with 0.9276 electrons
__made from a p-pi orbital ( 99.95% p)

17. A lone pair orbital for C2 with 0.2696 electrons
__made from a p-pi orbital ( 99.98% p)

18. A lone pair orbital for O3 with 0.9909 electrons
__made from a sp0.59 hybrid

19. A lone pair orbital for O3 with 0.9519 electrons
__made from a p-pi orbital ( 99.91% p 0.09% d)

20. A lone pair orbital for O3 with 0.8890 electrons
__made from a p3 hybrid

21. A lone pair orbital for C4 with 0.8975 electrons
__made from a p3 hybrid

-With core pairs on: O 1 C 2 O 3 C 4 C 7 -

Up Electrons

1. A bonding orbital for O1-C2 with 0.9966 electrons
__has 66.99% O 1 character in a sp2.38 hybrid
__has 33.01% C 2 character in a sp2.63 hybrid

2. A bonding orbital for O1-C7 with 0.9954 electrons
__has 68.40% O 1 character in a sp2.42 hybrid
__has 31.60% C 7 character in a s0.85 p3 hybrid

3. A bonding orbital for C2-O3 with 0.9980 electrons
__has 37.82% C 2 character in a sp1.92 hybrid
__has 62.18% O 3 character in a sp1.64 hybrid

4. A bonding orbital for C2-O3 with 0.9549 electrons
__has 53.31% C 2 character in a p3 hybrid
__has 46.69% O 3 character in a p3 hybrid

5. A bonding orbital for C2-C4 with 0.9972 electrons
__has 53.34% C 2 character in a sp1.59 hybrid
__has 46.66% C 4 character in a sp1.94 hybrid

6. A bonding orbital for C4-H5 with 0.9957 electrons
__has 56.15% C 4 character in a sp2.00 hybrid
__has 43.85% H 5 character in a s orbital

7. A bonding orbital for C4-H6 with 0.9952 electrons
__has 57.07% C 4 character in a sp2.05 hybrid
__has 42.93% H 6 character in a s orbital

8. A bonding orbital for C7-H8 with 0.9965 electrons
__has 59.43% C 7 character in a sp2.85 hybrid
__has 40.57% H 8 character in a s orbital

9. A bonding orbital for C7-H9 with 0.9975 electrons
__has 58.11% C 7 character in a sp2.83 hybrid
__has 41.89% H 9 character in a s orbital

10. A bonding orbital for C7-H10 with 0.9979 electrons
__has 58.05% C 7 character in a sp2.83 hybrid
__has 41.95% H10 character in a s orbital

16. A lone pair orbital for O1 with 0.9847 electrons
__made from a sp1.41 hybrid

17. A lone pair orbital for O1 with 0.9535 electrons
__made from a p3 hybrid

18. A lone pair orbital for O3 with 0.9902 electrons
__made from a sp0.60 hybrid

19. A lone pair orbital for O3 with 0.9461 electrons
__made from a p3 hybrid

-With core pairs on: O 1 C 2 O 3 C 4 C 7 -

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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, 20, for C4 is 75.9 kJ/mol.

The interaction of the second lone pair donor orbital, 17, for O1 with the second antibonding acceptor orbital, 144, for C2-O3 is 65.7 kJ/mol.

The interaction of the second lone pair donor orbital, 19, for O3 with the antibonding acceptor orbital, 141, for O1-C2 is 82.4 kJ/mol.

The interaction of the second lone pair donor orbital, 19, for O3 with the antibonding acceptor orbital, 145, for C2-C4 is 40.4 kJ/mol.

The interaction of lone pair donor orbital, 20, for C4 with the second antibonding acceptor orbital, 144, for C2-O3 is 26.1 kJ/mol.

The interaction of antibonding donor orbital, 141, for O1-C2 with the antibonding acceptor orbital, 146, for C4-H5 is 20.6 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.

24 ----- 1.608

23 ----- 1.110

22 ----- 0.572


21 ----- -0.622


20 -^--- -6.421

19 -^-v- -6.737

18 -^-v- -7.417


17 -^-v- -8.626


16 -^-v- -10.26

15 -^-v- -10.38

14 -^-v- -10.74


13 -^-v- -12.03
12 -^-v- -12.12

11 -^-v- -13.04


10 -^-v- -14.27


9 -^-v- -18.08

8 -^-v- -18.84


7 -^-v- -25.32


6 -^-v- -27.34


5 -^-v- -267.9

4 -^-v- -268.1


3 -^-v- -269.8


2 -^-v- -506.3


1 -^-v- -507.8

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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 = -267.8124393018 Hartrees

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