Methylpropionate radical cation, CH3CH2COOCH3+

O3
//
O1 - C2H6
/ \ /
H12 - C11 - H14H10 - C4 - C5 - H8
| / \
H13H9H7
The ion charge is 1. 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=-0.148
C2 charge= 0.626
O3 charge=-0.152
C4 charge=-0.205
C5 charge=-0.398
H6 charge= 0.187
H7 charge= 0.209
H8 charge= 0.188
H9 charge= 0.191
H10 charge= 0.192
C11 charge=-0.304
H12 charge= 0.259
H13 charge= 0.179
H14 charge= 0.174
with a dipole moment of 8.33676 Debye

Bond Lengths:

between O1 and C2: distance=1.311 ang___ between O1 and O3: distance=2.255 ang___
between O1 and C4: distance=2.526 ang___ between O1 and C11: distance=1.470 ang___
between C2 and O3: distance=1.224 ang___ between C2 and C4: distance=1.604 ang___
between C2 and C11: distance=2.452 ang___ between C4 and C5: distance=1.506 ang___
between C4 and H7: distance=2.126 ang___ between C4 and H9: distance=1.113 ang___
between C4 and H10: distance=1.114 ang___ between C5 and H6: distance=1.103 ang___
between C5 and H7: distance=1.114 ang___ between C5 and H8: distance=1.103 ang___
between C5 and H9: distance=2.184 ang___ between C5 and H10: distance=2.183 ang___
between C11 and H12: distance=1.103 ang___ between C11 and H13: distance=1.102 ang___
between C11 and H14: distance=1.102 ang___

Bond Angles:

for O3-C2-O1: angle=125.5 deg___ for C4-C2-O1: angle=119.7 deg___
for C5-C4-C2: angle=119.7 deg___ for H6-C5-C4: angle=112.7 deg___
for H7-C5-C4: angle=107.5 deg___ for H8-C5-C4: angle=112.7 deg___
for H9-C4-C2: angle=100.0 deg___ for H10-C4-C2: angle=99.91 deg___
for C11-O1-C2: angle=123.6 deg___ for H12-C11-O1: angle=103.4 deg___
for H13-C11-O1: angle=110.3 deg___ for H14-C11-O1: angle=110.3 deg___

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Bond Orders (Mulliken):

between O1 and C2: order=1.346___ between O1 and O3: order=-0.106___
between O1 and C4: order=-0.104___ between O1 and C11: order=0.578___
between C2 and O3: order=1.470___ between C2 and C4: order=0.719___
between C2 and C11: order=0.052___ between C4 and C5: order=0.757___
between C4 and H7: order=-0.062___ between C4 and H9: order=0.974___
between C4 and H10: order=0.968___ between C5 and H6: order=0.949___
between C5 and H7: order=1.001___ between C5 and H8: order=0.952___
between C5 and H9: order=-0.066___ between C5 and H10: order=-0.065___
between C11 and H12: order=0.950___ between C11 and H13: order=0.957___
between C11 and H14: order=0.960___

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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 0.9981 electrons
__has 66.68% O 1 character in a sp2.07 hybrid
__has 33.32% C 2 character in a sp2.05 hybrid

2. A bonding orbital for O1-C11 with 0.9925 electrons
__has 73.49% O 1 character in a sp2.04 hybrid
__has 26.51% C11 character in a s0.73 p3 hybrid

3. A bonding orbital for C2-O3 with 0.9981 electrons
__has 32.83% C 2 character in a sp2.14 hybrid
__has 67.17% O 3 character in a sp1.82 hybrid

4. A bonding orbital for C2-C4 with 0.9949 electrons
__has 52.02% C 2 character in a sp1.78 hybrid
__has 47.98% C 4 character in a s0.70 p3 hybrid

5. A bonding orbital for C4-C5 with 0.9970 electrons
__has 54.53% C 4 character in a sp1.91 hybrid
__has 45.47% C 5 character in a sp2.58 hybrid

6. A bonding orbital for C4-H9 with 0.9854 electrons
__has 61.95% C 4 character in a s0.92 p3 hybrid
__has 38.05% H 9 character in a s orbital

7. A bonding orbital for C4-H10 with 0.9853 electrons
__has 61.90% C 4 character in a s0.91 p3 hybrid
__has 38.10% H10 character in a s orbital

8. A bonding orbital for C5-H6 with 0.9951 electrons
__has 60.97% C 5 character in a s0.97 p3 hybrid
__has 39.03% H 6 character in a s orbital

9. A bonding orbital for C5-H7 with 0.9899 electrons
__has 61.66% C 5 character in a s0.90 p3 hybrid
__has 38.34% H 7 character in a s orbital

10. A bonding orbital for C5-H8 with 0.9951 electrons
__has 60.97% C 5 character in a s0.97 p3 hybrid
__has 39.03% H 8 character in a s orbital

11. A bonding orbital for C11-H12 with 0.9958 electrons
__has 61.50% C11 character in a sp2.80 hybrid
__has 38.50% H12 character in a s orbital

12. A bonding orbital for C11-H13 with 0.9966 electrons
__has 60.03% C11 character in a sp2.67 hybrid
__has 39.97% H13 character in a s orbital

13. A bonding orbital for C11-H14 with 0.9965 electrons
__has 59.93% C11 character in a sp2.68 hybrid
__has 40.07% H14 character in a s orbital

20. A lone pair orbital for O1 with 0.9804 electrons
__made from a sp1.87 hybrid

21. A lone pair orbital for O1 with 0.8835 electrons
__made from a p3 hybrid

22. A lone pair orbital for C2 with 0.2479 electrons
__made from a p-pi orbital ( 99.83% p 0.17% d)

23. A lone pair orbital for O3 with 0.9919 electrons
__made from a sp0.56 hybrid

24. A lone pair orbital for O3 with 0.9706 electrons
__made from a p3 hybrid

25. A lone pair orbital for O3 with 0.8788 electrons
__made from a p-pi orbital ( 99.83% p 0.17% d)

-With core pairs on: O 1 C 2 O 3 C 4 C 5 C11 -

Up Electrons

1. A bonding orbital for O1-C2 with 0.9928 electrons
__has 63.44% O 1 character in a sp2.37 hybrid
__has 36.56% C 2 character in a sp1.91 hybrid

2. A bonding orbital for O1-C11 with 0.9920 electrons
__has 73.38% O 1 character in a sp2.04 hybrid
__has 26.62% C11 character in a s0.73 p3 hybrid

3. A bonding orbital for C2-O3 with 0.9977 electrons
__has 36.24% C 2 character in a sp2.15 hybrid
__has 63.76% O 3 character in a sp1.60 hybrid

4. A bonding orbital for C2-C4 with 0.9497 electrons
__has 59.46% C 2 character in a sp1.91 hybrid
__has 40.54% C 4 character in a s0.67 p3 hybrid

5. A bonding orbital for C4-C5 with 0.9968 electrons
__has 53.93% C 4 character in a sp1.92 hybrid
__has 46.07% C 5 character in a sp2.56 hybrid

6. A bonding orbital for C4-H9 with 0.9804 electrons
__has 61.73% C 4 character in a s0.94 p3 hybrid
__has 38.27% H 9 character in a s orbital

7. A bonding orbital for C4-H10 with 0.9802 electrons
__has 61.67% C 4 character in a s0.93 p3 hybrid
__has 38.33% H10 character in a s orbital

8. A bonding orbital for C5-H6 with 0.9950 electrons
__has 61.04% C 5 character in a s0.98 p3 hybrid
__has 38.96% H 6 character in a s orbital

9. A bonding orbital for C5-H7 with 0.9889 electrons
__has 61.62% C 5 character in a s0.89 p3 hybrid
__has 38.38% H 7 character in a s orbital

10. A bonding orbital for C5-H8 with 0.9950 electrons
__has 61.04% C 5 character in a s0.97 p3 hybrid
__has 38.96% H 8 character in a s orbital

11. A bonding orbital for C11-H12 with 0.9945 electrons
__has 61.63% C11 character in a sp2.78 hybrid
__has 38.37% H12 character in a s orbital

12. A bonding orbital for C11-H13 with 0.9967 electrons
__has 59.99% C11 character in a sp2.68 hybrid
__has 40.01% H13 character in a s orbital

13. A bonding orbital for C11-H14 with 0.9967 electrons
__has 59.89% C11 character in a sp2.69 hybrid
__has 40.11% H14 character in a s orbital

20. A lone pair orbital for O1 with 0.9819 electrons
__made from a sp1.65 hybrid

21. A lone pair orbital for O1 with 0.8922 electrons
__made from a p3 hybrid

22. A lone pair orbital for C2 with 0.2884 electrons
__made from a p-pi orbital ( 99.76% p 0.24% d)

23. A lone pair orbital for O3 with 0.9911 electrons
__made from a sp0.61 hybrid

24. A lone pair orbital for O3 with 0.8274 electrons
__made from a p-pi orbital ( 99.81% p 0.19% d)

-With core pairs on: O 1 C 2 O 3 C 4 C 5 C11 -

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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 bonding donor orbital, 4, for C2-C4 with the third lone pair acceptor orbital, 25, for O3 is 88.5 kJ/mol.

The interaction of bonding donor orbital, 9, for C5-H7 with the antibonding acceptor orbital, 183, for C2-C4 is 19.9 kJ/mol.

The interaction of lone pair donor orbital, 20, for O1 with the antibonding acceptor orbital, 183, for C2-C4 is 22.3 kJ/mol.

The interaction of the second lone pair donor orbital, 21, for O1 with the lone pair acceptor orbital, 22, for C2 is 259. kJ/mol.

The interaction of the second lone pair donor orbital, 24, for O3 with the lone pair acceptor orbital, 22, for C2 is 515. 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.

28 ----- -3.451

27 ----- -4.024


26 ----- -5.041


25 ----- -7.706


24 -^--- -13.44

23 -^-v- -13.93

22 -^-v- -14.14

21 -^-v- -14.70

20 -^-v- -14.81

19 -^-v- -15.46

18 -^-v- -16.19

17 -^-v- -16.58

16 -^-v- -16.93


15 -^-v- -18.19

14 -^-v- -18.67

13 -^-v- -18.92

12 -^-v- -19.83


11 -^-v- -21.94


10 -^-v- -24.36


9 -^-v- -25.45


8 -^-v- -32.83


7 -^-v- -34.62


6 -^-v- -271.5


5 -^-v- -273.5

4 -^-v- -273.7


3 -^-v- -276.9


2 -^-v- -514.5

1 -^-v- -514.8

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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 = -307.4449405727 Hartrees

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