2-dehydro-propanoic acid radical, CH3CH•COOH

H10O3
| //
O1 - C2H7
\ /
C4 - C5 - H8
/ \
H9H6
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=-0.616
C2 charge= 0.573
O3 charge=-0.509
C4 charge=-0.069
C5 charge=-0.357
H6 charge= 0.132
H7 charge= 0.142
H8 charge= 0.132
H9 charge= 0.127
H10 charge= 0.443
with a dipole moment of 1.96045 Debye

Bond Lengths:

between O1 and C2: distance=1.386 ang___ between O1 and O3: distance=2.292 ang___
between O1 and C4: distance=2.364 ang___ between O1 and H10: distance=0.983 ang___
between C2 and O3: distance=1.240 ang___ between C2 and C4: distance=1.450 ang___
between O3 and C4: distance=2.394 ang___ between C4 and C5: distance=1.483 ang___
between C4 and H7: distance=2.143 ang___ between C4 and H9: distance=1.096 ang___
between C5 and H6: distance=1.110 ang___ between C5 and H7: distance=1.102 ang___
between C5 and H8: distance=1.110 ang___

Bond Angles:

for O3-C2-O1: angle=121.4 deg___ for C4-C2-O1: angle=112.9 deg___
for C5-C4-C2: angle=121.1 deg___ for H6-C5-C4: angle=110.9 deg___
for H7-C5-C4: angle=111.1 deg___ for H8-C5-C4: angle=110.8 deg___
for H9-C4-C2: angle=118.1 deg___ for H10-O1-C2: angle=105.3 deg___

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Bond Orders (Mulliken):

between O1 and C2: order=1.079___ between O1 and O3: order=-0.228___
between O1 and C4: order=-0.128___ between O1 and H10: order=0.841___
between C2 and O3: order=1.881___ between C2 and C4: order=1.073___
between O3 and C4: order=-0.058___ between C4 and C5: order=0.745___
between C4 and H7: order=-0.108___ between C4 and H9: order=0.923___
between C5 and H6: order=0.970___ between C5 and H7: order=1.016___
between C5 and H8: 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 0.9978 electrons
__has 67.13% O 1 character in a sp2.37 hybrid
__has 32.87% C 2 character in a sp2.53 hybrid

2. A bonding orbital for O1-H10 with 0.9944 electrons
__has 74.95% O 1 character in a s0.84 p3 hybrid
__has 25.05% H10 character in a s orbital

3. A bonding orbital for C2-O3 with 0.9987 electrons
__has 35.24% C 2 character in a sp1.88 hybrid
__has 64.76% O 3 character in a sp1.69 hybrid

4. A bonding orbital for C2-C4 with 0.9943 electrons
__has 48.67% C 2 character in a sp1.67 hybrid
__has 51.33% C 4 character in a sp2.07 hybrid

5. A bonding orbital for C4-C5 with 0.9958 electrons
__has 51.90% C 4 character in a sp1.73 hybrid
__has 48.10% C 5 character in a sp2.51 hybrid

6. A bonding orbital for C4-H9 with 0.9924 electrons
__has 61.71% C 4 character in a sp2.21 hybrid
__has 38.29% H 9 character in a s orbital

7. A bonding orbital for C5-H6 with 0.9965 electrons
__has 58.48% C 5 character in a s0.91 p3 hybrid
__has 41.52% H 6 character in a s orbital

8. A bonding orbital for C5-H7 with 0.9955 electrons
__has 61.01% C 5 character in a sp2.99 hybrid
__has 38.99% H 7 character in a s orbital

9. A bonding orbital for C5-H8 with 0.9965 electrons
__has 58.48% C 5 character in a s0.91 p3 hybrid
__has 41.52% H 8 character in a s orbital

15. A lone pair orbital for O1 with 0.9908 electrons
__made from a sp1.06 hybrid

16. A lone pair orbital for O1 with 0.9459 electrons
__made from a p-pi orbital ( 99.94% p 0.06% d)

17. A lone pair orbital for C2 with 0.2949 electrons
__made from a p-pi orbital ( 99.98% p)

18. A lone pair orbital for O3 with 0.9901 electrons
__made from a sp0.58 hybrid

19. A lone pair orbital for O3 with 0.9484 electrons
__made from a p3 hybrid

20. A lone pair orbital for O3 with 0.8751 electrons
__made from a p-pi orbital ( 99.88% p 0.12% d)

21. A lone pair orbital for C4 with 0.8640 electrons
__made from a p-pi orbital ( 99.95% p)

-With core pairs on: O 1 C 2 O 3 C 4 C 5 -

Up Electrons

1. A bonding orbital for O1-C2 with 0.9978 electrons
__has 66.76% O 1 character in a sp2.41 hybrid
__has 33.24% C 2 character in a sp2.65 hybrid

2. A bonding orbital for O1-H10 with 0.9949 electrons
__has 74.89% O 1 character in a s0.84 p3 hybrid
__has 25.11% H10 character in a s orbital

3. A bonding orbital for C2-O3 with 0.9987 electrons
__has 37.27% C 2 character in a sp1.91 hybrid
__has 62.73% O 3 character in a sp1.66 hybrid

4. A bonding orbital for C2-O3 with 0.9768 electrons
__has 42.14% C 2 character in a p-pi orbital ( 99.58% p 0.42% d)
__has 57.86% O 3 character in a p-pi orbital ( 99.79% p 0.21% d)

5. A bonding orbital for C2-C4 with 0.9943 electrons
__has 53.18% C 2 character in a sp1.58 hybrid
__has 46.82% C 4 character in a sp2.09 hybrid

6. A bonding orbital for C4-C5 with 0.9960 electrons
__has 47.52% C 4 character in a sp1.74 hybrid
__has 52.48% C 5 character in a sp2.40 hybrid

7. A bonding orbital for C4-H9 with 0.9933 electrons
__has 56.81% C 4 character in a sp2.19 hybrid
__has 43.19% H 9 character in a s orbital

8. A bonding orbital for C5-H6 with 0.9841 electrons
__has 61.52% C 5 character in a s0.90 p3 hybrid
__has 38.48% H 6 character in a s orbital

9. A bonding orbital for C5-H7 with 0.9953 electrons
__has 61.48% C 5 character in a s0.97 p3 hybrid
__has 38.52% H 7 character in a s orbital

10. A bonding orbital for C5-H8 with 0.9840 electrons
__has 61.53% C 5 character in a s0.90 p3 hybrid
__has 38.47% H 8 character in a s orbital

16. A lone pair orbital for O1 with 0.9910 electrons
__made from a sp1.05 hybrid

17. A lone pair orbital for O1 with 0.9522 electrons
__made from a p-pi orbital ( 99.94% p 0.06% d)

18. A lone pair orbital for O3 with 0.9896 electrons
__made from a sp0.60 hybrid

19. A lone pair orbital for O3 with 0.9451 electrons
__made from a p3 hybrid

-With core pairs on: O 1 C 2 O 3 C 4 C 5 -

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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 41.1 kJ/mol.

The interaction of bonding donor orbital, 8, for C5-H6 with the lone pair acceptor orbital, 20, for C4 is 23.1 kJ/mol.

The interaction of bonding donor orbital, 10, for C5-H8 with the lone pair acceptor orbital, 20, for C4 is 23.3 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 87.4 kJ/mol.

The interaction of the second lone pair donor orbital, 19, for O3 with the antibonding acceptor orbital, 141, for O1-C2 is 88.2 kJ/mol.

The interaction of the second lone pair donor orbital, 19, for O3 with the antibonding acceptor orbital, 145, for C2-C4 is 41.9 kJ/mol.

The interaction of lone pair donor orbital, 20, for C4 with the second antibonding acceptor orbital, 144, for C2-O3 is 179. 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 ----- 1.931

23 ----- 1.655

22 ----- 0.885


21 ----- -0.334


20 -^--- -5.689


19 -^-v- -6.709


18 -^-v- -7.879


17 -^-v- -9.275

16 -^-v- -9.929

15 -^-v- -10.35
14 -^-v- -10.43

13 -^-v- -11.30

12 -^-v- -11.65


11 -^-v- -12.78


10 -^-v- -14.24


9 -^-v- -17.08


8 -^-v- -19.84


7 -^-v- -25.04


6 -^-v- -27.30


5 -^-v- -266.7


4 -^-v- -267.7


3 -^-v- -269.7


2 -^-v- -506.3


1 -^-v- -507.6

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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 = -267.8494053370 Hartrees

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