CH3OOCCH2+, methyl-dehydro-acetate cation

O3
/
H8O1 - C2 |
\ / \
C7 - H10C4 - H6
| \
H9H5
The ion charge is 1.

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=-0.119
C2 charge= 0.563
O3 charge=-0.082
C4 charge=-0.260
H5 charge= 0.270
H6 charge= 0.271
C7 charge=-0.236
H8 charge= 0.232
H9 charge= 0.181
H10 charge= 0.180
with a dipole moment of 7.48176 Debye

Bond Lengths:

between O1 and C2: distance=1.261 ang___ between O1 and O3: distance=2.320 ang___
between O1 and C4: distance=2.648 ang___ between O1 and C7: distance=1.513 ang___
between C2 and O3: distance=1.281 ang___ between C2 and C4: distance=1.445 ang___
between O3 and C4: distance=1.613 ang___ between C4 and H5: distance=1.098 ang___
between C4 and H6: distance=1.098 ang___ between C7 and H8: distance=1.097 ang___
between C7 and H9: distance=1.099 ang___ between C7 and H10: distance=1.099 ang___

Bond Angles:

for O3-C2-O1: angle=131.6 deg___ for C4-C2-O1: angle=156.1 deg___
for H5-C4-C2: angle=119.7 deg___ for H6-C4-C2: angle=119.7 deg___
for C7-O1-C2: angle=120.5 deg___ for H8-C7-O1: angle=103.3 deg___
for H9-C7-O1: angle=108.0 deg___ for H10-C7-O1: angle=108.1 deg___

Top of page.

Bond Orders (Mulliken):

between O1 and C2: order=1.195___ between O1 and O3: order=-0.088___
between O1 and C4: order=-0.053___ between O1 and C7: order=0.557___
between C2 and O3: order=1.412___ between C2 and C4: order=1.240___
between O3 and C4: order=0.624___ between C4 and H5: order=0.903___
between C4 and H6: order=0.903___ between C7 and H8: order=0.950___
between C7 and H9: order=0.953___ between C7 and H10: order=0.954___

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.

Hybridization in the Best Lewis Structure

1. A bonding orbital for O1-C2 with 1.9967 electrons
__has 64.69% O 1 character in a sp2.00 hybrid
__has 35.31% C 2 character in a sp1.75 hybrid

2. A bonding orbital for O1-C2 with 1.9912 electrons
__has 84.54% O 1 character in a p-pi orbital ( 99.89% p 0.11% d)
__has 15.46% C 2 character in a p-pi orbital ( 99.21% p 0.79% d)

3. A bonding orbital for O1-C7 with 1.9783 electrons
__has 74.64% O 1 character in a sp2.54 hybrid
__has 25.36% C 7 character in a s0.67 p3 hybrid

4. A bonding orbital for C2-O3 with 1.9853 electrons
__has 34.49% C 2 character in a sp2.61 hybrid
__has 65.51% O 3 character in a sp2.72 hybrid

5. A bonding orbital for C2-C4 with 1.9894 electrons
__has 51.18% C 2 character in a sp1.76 hybrid
__has 48.82% C 4 character in a sp2.77 hybrid

6. A bonding orbital for O3-C4 with 1.9358 electrons
__has 71.83% O 3 character in a s0.24 p3 hybrid
__has 28.17% C 4 character in a s0.24 p3 hybrid

7. A bonding orbital for C4-H5 with 1.9860 electrons
__has 63.13% C 4 character in a sp2.01 hybrid
__has 36.87% H 5 character in a s orbital

8. A bonding orbital for C4-H6 with 1.9860 electrons
__has 63.13% C 4 character in a sp2.01 hybrid
__has 36.87% H 6 character in a s orbital

9. A bonding orbital for C7-H8 with 1.9930 electrons
__has 61.76% C 7 character in a sp2.64 hybrid
__has 38.24% H 8 character in a s orbital

10. A bonding orbital for C7-H9 with 1.9938 electrons
__has 60.20% C 7 character in a sp2.66 hybrid
__has 39.80% H 9 character in a s orbital

11. A bonding orbital for C7-H10 with 1.9938 electrons
__has 60.19% C 7 character in a sp2.66 hybrid
__has 39.81% H10 character in a s orbital

17. A lone pair orbital for O1 with 1.9485 electrons
__made from a sp1.59 hybrid

18. A lone pair orbital for O3 with 1.9884 electrons
__made from a sp0.52 hybrid

19. A lone pair orbital for O3 with 1.7165 electrons
__made from a p-pi orbital ( 99.84% p 0.16% d)

141. A antibonding orbital for O1-C2 with 0.2736 electrons
__has 15.46% O 1 character in a p-pi orbital ( 99.89% p 0.11% d)
__has 84.54% C 2 character in a p-pi orbital ( 99.21% p 0.79% d)

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

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, 3, for O1-C7 with the antibonding acceptor orbital, 143, for C2-O3 is 41.1 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-O3 with the antibonding acceptor orbital, 145, for O3-C4 is 26.3 kJ/mol.

The interaction of bonding donor orbital, 6, for O3-C4 with the antibonding acceptor orbital, 140, for O1-C2 is 162. kJ/mol.

The interaction of bonding donor orbital, 6, for O3-C4 with the antibonding acceptor orbital, 143, for C2-O3 is 44.8 kJ/mol.

The interaction of bonding donor orbital, 7, for C4-H5 with the second antibonding acceptor orbital, 141, for O1-C2 is 25.4 kJ/mol.

The interaction of bonding donor orbital, 8, for C4-H6 with the second antibonding acceptor orbital, 141, for O1-C2 is 25.4 kJ/mol.

The interaction of lone pair donor orbital, 17, for O1 with the antibonding acceptor orbital, 144, for C2-C4 is 75.0 kJ/mol.

The interaction of the second lone pair donor orbital, 19, for O3 with the second antibonding acceptor orbital, 141, for O1-C2 is 528. 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.

23 ----- -4.279


22 ----- -5.806


21 ----- -7.870

20 ----- -8.648


19 -^-v- -14.40

18 -^-v- -14.66

17 -^-v- -15.62
16 -^-v- -15.67


15 -^-v- -16.89

14 -^-v- -17.50


13 -^-v- -18.61

12 -^-v- -19.57

11 -^-v- -19.69

10 -^-v- -20.66


9 -^-v- -24.18

8 -^-v- -24.74


7 -^-v- -34.07


6 -^-v- -35.60


5 -^-v- -273.7


4 -^-v- -275.1


3 -^-v- -277.5


2 -^-v- -515.1

1 -^-v- -515.4

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 = -267.5127163752 Hartrees

Top of page.

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