O-dehydro-propanoic acid radical, CH3CH2COO•

O3
//
O1 = C2H10
\ /
H9 - C4H6
| /
H7 - C5
\
H8
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=-0.315
C2 charge= 0.487
O3 charge=-0.315
C4 charge= 0.016
C5 charge=-0.226
H6 charge= 0.085
H7 charge= 0.085
H8 charge= 0.073
H9 charge= 0.054
H10 charge= 0.054
with a dipole moment of 3.60103 Debye

Bond Lengths:

between O1 and C2: distance=1.277 ang___ between O1 and O3: distance=2.119 ang___
between C2 and O3: distance=1.277 ang___ between C2 and C4: distance=1.501 ang___
between C2 and C5: distance=2.519 ang___ between C4 and C5: distance=1.550 ang___
between C4 and H9: distance=1.107 ang___ between C4 and H10: distance=1.107 ang___
between C5 and H6: distance=1.102 ang___ between C5 and H7: distance=1.102 ang___
between C5 and H8: distance=1.102 ang___

Bond Angles:

for O3-C2-O1: angle=112.0 deg___ for C4-C2-O1: angle=123.9 deg___
for C5-C4-C2: angle=111.3 deg___ for H6-C5-C4: angle=110.7 deg___
for H7-C5-C4: angle=110.8 deg___ for H8-C5-C4: angle=110.2 deg___
for H9-C4-C2: angle=107.8 deg___ for H10-C4-C2: angle=107.8 deg___

Top of page.

Bond Orders (Mulliken):

between O1 and C2: order=1.591___ between O1 and O3: order=0.051___
between C2 and O3: order=1.591___ between C2 and C4: order=0.741___
between C2 and C5: order=-0.087___ between C4 and C5: order=0.871___
between C4 and H9: order=0.965___ between C4 and H10: order=0.965___
between C5 and H6: order=0.979___ between C5 and H7: order=0.978___
between C5 and H8: order=0.977___

Top of page.

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 0.9986 electrons
__has 65.33% O 1 character in a sp1.99 hybrid
__has 34.67% C 2 character in a sp2.25 hybrid

2. A bonding orbital for C2-O3 with 0.9986 electrons
__has 34.67% C 2 character in a sp2.25 hybrid
__has 65.33% O 3 character in a sp1.99 hybrid

3. A bonding orbital for C2-C4 with 0.9968 electrons
__has 48.64% C 2 character in a sp1.57 hybrid
__has 51.36% C 4 character in a s0.98 p3 hybrid

4. A bonding orbital for C4-C5 with 0.9895 electrons
__has 53.65% C 4 character in a sp2.45 hybrid
__has 46.35% C 5 character in a sp2.68 hybrid

5. A bonding orbital for C4-H9 with 0.9900 electrons
__has 61.87% C 4 character in a s0.91 p3 hybrid
__has 38.13% H 9 character in a s orbital

6. A bonding orbital for C4-H10 with 0.9899 electrons
__has 61.87% C 4 character in a s0.91 p3 hybrid
__has 38.13% H10 character in a s orbital

7. A bonding orbital for C5-H6 with 0.9963 electrons
__has 60.14% C 5 character in a s0.96 p3 hybrid
__has 39.86% H 6 character in a s orbital

8. A bonding orbital for C5-H7 with 0.9964 electrons
__has 60.14% C 5 character in a s0.96 p3 hybrid
__has 39.86% H 7 character in a s orbital

9. A bonding orbital for C5-H8 with 0.9951 electrons
__has 59.86% C 5 character in a s0.96 p3 hybrid
__has 40.14% H 8 character in a s orbital

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

16. A lone pair orbital for O1 with 0.9728 electrons
__made from a p3 hybrid

17. A lone pair orbital for O1 with 0.8666 electrons
__made from a p-pi orbital ( 99.89% p 0.11% d)

18. A lone pair orbital for C2 with 0.2757 electrons
__made from a p-pi orbital ( 99.81% p 0.19% d)

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

20. A lone pair orbital for O3 with 0.9728 electrons
__made from a p3 hybrid

21. A lone pair orbital for O3 with 0.8666 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 C 5 -

Up Electrons

1. A bonding orbital for O1-C2 with 0.9610 electrons
__has 59.80% O 1 character in a sp2.02 hybrid
__has 40.20% C 2 character in a sp2.71 hybrid

2. A antibonding orbital for O1-O3 with 0.9332 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 0.9610 electrons
__has 40.20% C 2 character in a sp2.71 hybrid
__has 59.80% O 3 character in a sp2.02 hybrid

4. A bonding orbital for C2-C4 with 0.9199 electrons
__has 58.66% C 2 character in a sp1.14 hybrid
__has 41.34% C 4 character in a s0.88 p3 hybrid

5. A bonding orbital for C4-C5 with 0.9867 electrons
__has 52.83% C 4 character in a sp2.35 hybrid
__has 47.17% C 5 character in a sp2.65 hybrid

6. A bonding orbital for C4-H9 with 0.9883 electrons
__has 60.77% C 4 character in a s0.94 p3 hybrid
__has 39.23% H 9 character in a s orbital

7. A bonding orbital for C4-H10 with 0.9883 electrons
__has 60.77% C 4 character in a s0.93 p3 hybrid
__has 39.23% H10 character in a s orbital

8. A bonding orbital for C5-H6 with 0.9961 electrons
__has 60.26% C 5 character in a s0.95 p3 hybrid
__has 39.74% H 6 character in a s orbital

9. A bonding orbital for C5-H7 with 0.9961 electrons
__has 60.26% C 5 character in a s0.95 p3 hybrid
__has 39.74% H 7 character in a s orbital

10. A bonding orbital for C5-H8 with 0.9909 electrons
__has 60.28% C 5 character in a s0.97 p3 hybrid
__has 39.72% H 8 character in a s orbital

16. A lone pair orbital for O1 with 0.9902 electrons
__made from a sp0.59 hybrid

17. A lone pair orbital for O1 with 0.8390 electrons
__made from a p3 hybrid

18. A lone pair orbital for C2 with 0.3279 electrons
__made from a p-pi orbital ( 99.83% p 0.17% d)

19. A lone pair orbital for O3 with 0.9902 electrons
__made from a sp0.59 hybrid

20. A lone pair orbital for O3 with 0.8391 electrons
__made from a p3 hybrid

142. A bonding orbital for O1-O3 with 0.1576 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 C 5 -

Top of page.

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, 142, for O1-O3 is 109. kJ/mol.

The interaction of antibonding donor orbital, 2, for O1-O3 with the antibonding acceptor orbital, 141, for O1-C2 is 52.5 kJ/mol.

The interaction of antibonding donor orbital, 2, for O1-O3 with the antibonding acceptor orbital, 143, for C2-O3 is 52.5 kJ/mol.

The interaction of bonding donor orbital, 3, for C2-O3 with the bonding acceptor orbital, 142, for O1-O3 is 109. kJ/mol.

The interaction of bonding donor orbital, 4, for C2-C4 with the bonding acceptor orbital, 142, for O1-O3 is 68.9 kJ/mol.

The interaction of the second lone pair donor orbital, 17, for O1 with the lone pair acceptor orbital, 18, for C2 is 455. kJ/mol.

The interaction of the second lone pair donor orbital, 20, for O3 with the lone pair acceptor orbital, 18, for C2 is 455. kJ/mol.

Top of page.

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 ----- 2.408

23 ----- 1.498

22 ----- 1.178


21 ----- -1.919


20 -^--- -7.889

19 -^-v- -8.124

18 -^-v- -8.328

17 -^-v- -9.231

16 -^-v- -9.719

15 -^-v- -10.17


14 -^-v- -11.17

13 -^-v- -11.83

12 -^-v- -12.35

11 -^-v- -12.72


10 -^-v- -13.74


9 -^-v- -16.66


8 -^-v- -19.99


7 -^-v- -25.24


6 -^-v- -28.19


5 -^-v- -266.8

4 -^-v- -267.4


3 -^-v- -270.3


2 -^-v- -508.1 1 -^-v- -508.1

Top of page.

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 = -267.8318423301 Hartrees

Top of page.

-> Return to Molecular Structure Page. -> Return to Chemistry Home Page