CH3COH=CHCH2CH2+•, pentenol radical cation, (see note)

H5H6
| /
H9C4H14
\ / \ /
C7 - H8C3 - C13 - H16
/ / \
C10H1 - O2H15
/ |
H12H11
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

H1 charge= 0.311
O2 charge=-0.315
C3 charge= 0.607
C4 charge=-0.387
H5 charge= 0.193
H6 charge= 0.160
C7 charge= 0.094
H8 charge= 0.076
H9 charge= 0.129
C10 charge=-0.363
H11 charge= 0.179
H12 charge= 0.192
C13 charge=-0.568
H14 charge= 0.213
H15 charge= 0.237
H16 charge= 0.239
with a dipole moment of 8.98651 Debye

Bond Lengths:

between H1 and O2: distance=1.082 ang___ between H1 and C10: distance=1.656 ang___
between O2 and C3: distance=1.284 ang___ between C3 and C4: distance=1.497 ang___
between C3 and C13: distance=1.476 ang___ between C4 and H5: distance=1.116 ang___
between C4 and H6: distance=1.105 ang___ between C4 and C7: distance=1.552 ang___
between C7 and H8: distance=1.105 ang___ between C7 and H9: distance=1.116 ang___
between C7 and C10: distance=1.499 ang___ between C10 and H11: distance=1.101 ang___
between C10 and H12: distance=1.097 ang___ between C13 and H14: distance=1.105 ang___
between C13 and H15: distance=1.101 ang___ between C13 and H16: distance=1.113 ang___

Bond Angles:

for C3-O2-H1: angle=109.3 deg___ for C4-C3-O2: angle=119.9 deg___
for H5-C4-C3: angle=105.0 deg___ for H6-C4-C3: angle=109.6 deg___
for C7-C4-C3: angle=113.2 deg___ for H8-C7-C4: angle=109.8 deg___
for H9-C7-C4: angle=107.3 deg___ for C10-C7-C4: angle=113.4 deg___
for H11-C10-C7: angle=119.3 deg___ for H12-C10-C7: angle=119.4 deg___
for C13-C3-O2: angle=117.3 deg___ for H14-C13-C3: angle=110.9 deg___
for H15-C13-C3: angle=112.1 deg___ for H16-C13-C3: angle=107.1 deg___

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Bond Orders (Mulliken):

between H1 and O2: order=0.693___ between H1 and C10: order=0.228___
between O2 and C3: order=1.524___ between C3 and C4: order=0.982___
between C3 and C13: order=1.013___ between C4 and H5: order=0.916___
between C4 and H6: order=0.950___ between C4 and C7: order=0.920___
between C7 and H8: order=0.968___ between C7 and H9: order=0.949___
between C7 and C10: order=0.905___ between C10 and H11: order=0.947___
between C10 and H12: order=0.945___ between C13 and H14: order=0.936___
between C13 and H15: order=0.951___ between C13 and H16: order=0.915___

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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 H1-O2 with 0.9915 electrons
__has 16.69% H 1 character in a s orbital
__has 83.31% O 2 character in a sp2.84 hybrid

2. A bonding orbital for O2-C3 with 0.9979 electrons
__has 67.96% O 2 character in a sp1.78 hybrid
__has 32.04% C 3 character in a sp2.52 hybrid

3. A bonding orbital for O2-C3 with 0.9965 electrons
__has 84.26% O 2 character in a p3 hybrid
__has 15.74% C 3 character in a p3 hybrid

4. A bonding orbital for C3-C4 with 0.9947 electrons
__has 50.36% C 3 character in a sp1.80 hybrid
__has 49.64% C 4 character in a sp2.95 hybrid

5. A bonding orbital for C3-C13 with 0.9949 electrons
__has 51.31% C 3 character in a sp1.77 hybrid
__has 48.69% C13 character in a sp2.64 hybrid

6. A bonding orbital for C4-H5 with 0.9738 electrons
__has 62.49% C 4 character in a s0.82 p3 hybrid
__has 37.51% H 5 character in a s orbital

7. A bonding orbital for C4-H6 with 0.9867 electrons
__has 62.57% C 4 character in a s0.95 p3 hybrid
__has 37.43% H 6 character in a s orbital

8. A bonding orbital for C4-C7 with 0.9923 electrons
__has 53.06% C 4 character in a sp2.43 hybrid
__has 46.94% C 7 character in a sp2.77 hybrid

9. A bonding orbital for C7-H8 with 0.9929 electrons
__has 60.66% C 7 character in a s0.92 p3 hybrid
__has 39.34% H 8 character in a s orbital

10. A bonding orbital for C7-H9 with 0.9941 electrons
__has 60.08% C 7 character in a s0.83 p3 hybrid
__has 39.92% H 9 character in a s orbital

11. A bonding orbital for C7-C10 with 0.9977 electrons
__has 50.11% C 7 character in a sp2.51 hybrid
__has 49.89% C10 character in a sp2.19 hybrid

12. A bonding orbital for C10-H11 with 0.9954 electrons
__has 61.64% C10 character in a sp2.57 hybrid
__has 38.36% H11 character in a s orbital

13. A bonding orbital for C10-H12 with 0.9955 electrons
__has 62.73% C10 character in a sp2.26 hybrid
__has 37.27% H12 character in a s orbital

14. A bonding orbital for C13-H14 with 0.9859 electrons
__has 62.24% C13 character in a s0.96 p3 hybrid
__has 37.76% H14 character in a s orbital

15. A bonding orbital for C13-H15 with 0.9930 electrons
__has 62.96% C13 character in a sp2.84 hybrid
__has 37.04% H15 character in a s orbital

16. A bonding orbital for C13-H16 with 0.9746 electrons
__has 62.73% C13 character in a s0.87 p3 hybrid
__has 37.27% H16 character in a s orbital

23. A lone pair orbital for O2 with 0.9867 electrons
__made from a sp1.62 hybrid

24. A lone pair orbital for C10 with 0.8843 electrons
__made from a s0.34 p3 hybrid

-With core pairs on: O 2 C 3 C 4 C 7 C10 C13 -

Up Electrons

1. A bonding orbital for H1-O2 with 0.9775 electrons
__has 23.61% H 1 character in a s orbital
__has 76.39% O 2 character in a s0.73 p3 hybrid

2. A bonding orbital for O2-C3 with 0.9980 electrons
__has 67.32% O 2 character in a sp1.72 hybrid
__has 32.68% C 3 character in a sp2.51 hybrid

3. A bonding orbital for O2-C3 with 0.9962 electrons
__has 82.83% O 2 character in a p3 hybrid
__has 17.17% C 3 character in a p3 hybrid

4. A bonding orbital for C3-C4 with 0.9939 electrons
__has 50.70% C 3 character in a sp1.81 hybrid
__has 49.30% C 4 character in a sp2.92 hybrid

5. A bonding orbital for C3-C13 with 0.9919 electrons
__has 51.76% C 3 character in a sp1.75 hybrid
__has 48.24% C13 character in a sp2.66 hybrid

6. A bonding orbital for C4-H5 with 0.9741 electrons
__has 62.30% C 4 character in a s0.82 p3 hybrid
__has 37.70% H 5 character in a s orbital

7. A bonding orbital for C4-H6 with 0.9871 electrons
__has 62.33% C 4 character in a s0.95 p3 hybrid
__has 37.67% H 6 character in a s orbital

8. A bonding orbital for C4-C7 with 0.9891 electrons
__has 51.71% C 4 character in a sp2.45 hybrid
__has 48.29% C 7 character in a sp2.92 hybrid

9. A bonding orbital for C7-H8 with 0.9917 electrons
__has 61.32% C 7 character in a s0.88 p3 hybrid
__has 38.68% H 8 character in a s orbital

10. A bonding orbital for C7-H9 with 0.9708 electrons
__has 64.43% C 7 character in a s0.89 p3 hybrid
__has 35.57% H 9 character in a s orbital

11. A bonding orbital for C7-C10 with 0.9961 electrons
__has 53.98% C 7 character in a sp2.45 hybrid
__has 46.02% C10 character in a sp1.79 hybrid

12. A bonding orbital for C10-H11 with 0.9950 electrons
__has 57.71% C10 character in a sp2.16 hybrid
__has 42.29% H11 character in a s orbital

13. A bonding orbital for C10-H12 with 0.9959 electrons
__has 58.51% C10 character in a sp2.08 hybrid
__has 41.49% H12 character in a s orbital

14. A bonding orbital for C13-H14 with 0.9861 electrons
__has 62.19% C13 character in a s0.96 p3 hybrid
__has 37.81% H14 character in a s orbital

15. A bonding orbital for C13-H15 with 0.9931 electrons
__has 62.89% C13 character in a sp2.84 hybrid
__has 37.11% H15 character in a s orbital

16. A bonding orbital for C13-H16 with 0.9747 electrons
__has 62.65% C13 character in a s0.87 p3 hybrid
__has 37.35% H16 character in a s orbital

23. A lone pair orbital for O2 with 0.9857 electrons
__made from a sp1.28 hybrid

-With core pairs on: O 2 C 3 C 4 C 7 C10 C13 -

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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, 1, for H1-O2 with the lone pair acceptor orbital, 24, for C10 is 28.2 kJ/mol.

The interaction of bonding donor orbital, 6, for C4-H5 with the second antibonding acceptor orbital, 167, for O2-C3 is 33.5 kJ/mol.

The interaction of bonding donor orbital, 10, for C7-H9 with the lone pair acceptor orbital, 24, for C10 is 41.6 kJ/mol.

The interaction of bonding donor orbital, 16, for C13-H16 with the second antibonding acceptor orbital, 167, for O2-C3 is 36.3 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 ----- -2.712

27 ----- -3.127

26 ----- -3.559


25 ----- -8.533


24 -^--- -10.50


23 -^-v- -13.57

22 -^-v- -14.17

21 -^-v- -14.37

20 -^-v- -14.77

19 -^-v- -14.91

18 -^-v- -15.38

17 -^-v- -15.55

16 -^-v- -16.15

15 -^-v- -17.05

14 -^-v- -17.48

13 -^-v- -18.20


12 -^-v- -20.05

11 -^-v- -20.79


10 -^-v- -22.50


9 -^-v- -24.59

8 -^-v- -25.54


7 -^-v- -33.42


6 -^-v- -271.7

5 -^-v- -271.8

4 -^-v- -271.9

3 -^-v- -272.3


2 -^-v- -275.5


1 -^-v- -514.1

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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 = -271.5387582757 Hartrees

Note: This ion results from the McLafferty rearrangemnt of 2-pentanone radical cation, CH3CH2CH2COCH3+•. Other similar conformations of this ion dissociate in calculations to ethylene and propenol radical cation, H2C=COHCH3+•. So this calculation should be considered a transient intermediate, at best. Other lower energy metastable conformers may also exist. The 'all trans' pentenol radical cation trans conformer is higher in energy.
* The Lewis Structure calculation (NBO analysis) was run without diffuse functions to decrease the size of the calculation.

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