CH3CH2CH2COCH3+•, 2-pentanone radical cation

H14O13
| //
H16 - C12 - C9
| \
H15H8C6 - H11
| / |
H3 - C1 - C2H10
/ | \
H4H5H7
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

C1 charge=-0.398
C2 charge= 0.090
H3 charge= 0.148
H4 charge= 0.168
H5 charge= 0.139
C6 charge=-0.310
H7 charge= 0.145
H8 charge= 0.087
C9 charge= 0.532
H10 charge= 0.173
H11 charge= 0.177
C12 charge=-0.479
O13 charge=-0.129
H14 charge= 0.237
H15 charge= 0.225
H16 charge= 0.192
with a dipole moment of 10.30796 Debye

Bond Lengths:

between C1 and C2: distance=1.523 ang___ between C1 and H3: distance=1.111 ang___
between C1 and H4: distance=1.105 ang___ between C1 and H5: distance=1.104 ang___
between C2 and C6: distance=1.529 ang___ between C2 and H7: distance=1.127 ang___
between C2 and H8: distance=1.107 ang___ between C6 and C9: distance=1.603 ang___
between C6 and H10: distance=1.107 ang___ between C6 and H11: distance=1.103 ang___
between C9 and C12: distance=1.515 ang___ between C9 and O13: distance=1.209 ang___
between C12 and H14: distance=1.100 ang___ between C12 and H15: distance=1.110 ang___
between C12 and H16: distance=1.102 ang___

Bond Angles:

for H3-C1-C2: angle=111.8 deg___ for H4-C1-C2: angle=110.1 deg___
for H5-C1-C2: angle=112.7 deg___ for C6-C2-C1: angle=118.9 deg___
for H7-C2-C1: angle=108.6 deg___ for H8-C2-C1: angle=112.3 deg___
for C9-C6-C2: angle=111.3 deg___ for H10-C6-C2: angle=113.3 deg___
for H11-C6-C2: angle=111.3 deg___ for C12-C9-C6: angle=118.5 deg___
for O13-C9-C6: angle=117.1 deg___ for H14-C12-C9: angle=110.1 deg___
for H15-C12-C9: angle=105.3 deg___ for H16-C12-C9: angle=110.6 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=0.959___ between C1 and H3: order=0.965___
between C1 and H4: order=0.968___ between C1 and H5: order=0.969___
between C2 and C6: order=0.935___ between C2 and H7: order=0.960___
between C2 and H8: order=0.958___ between C6 and C9: order=0.817___
between C6 and H10: order=0.946___ between C6 and H11: order=0.950___
between C9 and C12: order=0.962___ between C9 and O13: order=1.674___
between C12 and H14: order=0.946___ between C12 and H15: order=0.904___
between C12 and H16: order=0.929___

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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. * 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 C1-C2 with 0.9973 electrons
__has 47.80% C 1 character in a sp2.47 hybrid
__has 52.20% C 2 character in a sp2.22 hybrid

2. A bonding orbital for C1-H3 with 0.9954 electrons
__has 59.08% C 1 character in a s0.89 p3 hybrid
__has 40.92% H 3 character in a s orbital

3. A bonding orbital for C1-H4 with 0.9937 electrons
__has 61.44% C 1 character in a s0.95 p3 hybrid
__has 38.56% H 4 character in a s orbital

4. A bonding orbital for C1-H5 with 0.9958 electrons
__has 59.68% C 1 character in a s0.96 p3 hybrid
__has 40.32% H 5 character in a s orbital

5. A bonding orbital for C2-C6 with 0.9875 electrons
__has 45.98% C 2 character in a sp2.80 hybrid
__has 54.02% C 6 character in a sp2.24 hybrid

6. A bonding orbital for C2-H7 with 0.9854 electrons
__has 60.70% C 2 character in a s0.73 p3 hybrid
__has 39.30% H 7 character in a s orbital

7. A bonding orbital for C2-H8 with 0.9919 electrons
__has 60.59% C 2 character in a s0.91 p3 hybrid
__has 39.41% H 8 character in a s orbital

8. A bonding orbital for C6-C9 with 0.9936 electrons
__has 48.34% C 6 character in a s0.77 p3 hybrid
__has 51.66% C 9 character in a sp2.00 hybrid

9. A bonding orbital for C6-H10 with 0.9899 electrons
__has 61.62% C 6 character in a s0.95 p3 hybrid
__has 38.38% H10 character in a s orbital

10. A bonding orbital for C6-H11 with 0.9899 electrons
__has 62.51% C 6 character in a s0.98 p3 hybrid
__has 37.49% H11 character in a s orbital

11. A bonding orbital for C9-C12 with 0.9968 electrons
__has 50.47% C 9 character in a sp1.71 hybrid
__has 49.53% C12 character in a sp2.98 hybrid

12. A bonding orbital for C9-O13 with 0.9989 electrons
__has 30.92% C 9 character in a sp2.31 hybrid
__has 69.08% O13 character in a sp1.48 hybrid

13. A bonding orbital for C9-O13 with 0.9986 electrons
__has 15.20% C 9 character in a p3 hybrid
__has 84.80% O13 character in a p3 hybrid

14. A bonding orbital for C12-H14 with 0.9938 electrons
__has 62.99% C12 character in a sp2.88 hybrid
__has 37.01% H14 character in a s orbital

15. A bonding orbital for C12-H15 with 0.9778 electrons
__has 63.35% C12 character in a s0.92 p3 hybrid
__has 36.65% H15 character in a s orbital

16. A bonding orbital for C12-H16 with 0.9886 electrons
__has 63.27% C12 character in a sp2.86 hybrid
__has 36.73% H16 character in a s orbital

23. A lone pair orbital for O13 with 0.9913 electrons
__made from a sp0.67 hybrid

24. A lone pair orbital for O13 with 0.9746 electrons
__made from a p3 hybrid

-With core pairs on: C 1 C 2 C 6 C 9 C12 O13 -

Up Electrons

1. A bonding orbital for C1-C2 with 0.9972 electrons
__has 47.76% C 1 character in a sp2.47 hybrid
__has 52.24% C 2 character in a sp2.23 hybrid

2. A bonding orbital for C1-H3 with 0.9954 electrons
__has 59.08% C 1 character in a s0.89 p3 hybrid
__has 40.92% H 3 character in a s orbital

3. A bonding orbital for C1-H4 with 0.9938 electrons
__has 61.42% C 1 character in a s0.95 p3 hybrid
__has 38.58% H 4 character in a s orbital

4. A bonding orbital for C1-H5 with 0.9958 electrons
__has 59.67% C 1 character in a s0.96 p3 hybrid
__has 40.33% H 5 character in a s orbital

5. A bonding orbital for C2-C6 with 0.9859 electrons
__has 46.64% C 2 character in a sp2.78 hybrid
__has 53.36% C 6 character in a sp2.17 hybrid

6. A bonding orbital for C2-H7 with 0.9791 electrons
__has 61.17% C 2 character in a s0.73 p3 hybrid
__has 38.83% H 7 character in a s orbital

7. A bonding orbital for C2-H8 with 0.9917 electrons
__has 60.71% C 2 character in a s0.90 p3 hybrid
__has 39.29% H 8 character in a s orbital

8. A bonding orbital for C6-C9 with 0.9291 electrons
__has 38.63% C 6 character in a s0.71 p3 hybrid
__has 61.37% C 9 character in a sp2.06 hybrid

9. A bonding orbital for C6-H10 with 0.9845 electrons
__has 61.56% C 6 character in a s0.97 p3 hybrid
__has 38.44% H10 character in a s orbital

10. A bonding orbital for C6-H11 with 0.9908 electrons
__has 61.72% C 6 character in a s0.98 p3 hybrid
__has 38.28% H11 character in a s orbital

11. A bonding orbital for C9-C12 with 0.9614 electrons
__has 57.34% C 9 character in a sp1.63 hybrid
__has 42.66% C12 character in a s0.92 p3 hybrid

12. A bonding orbital for C9-O13 with 0.9989 electrons
__has 34.63% C 9 character in a sp2.34 hybrid
__has 65.37% O13 character in a sp1.31 hybrid

13. A bonding orbital for C9-O13 with 0.9976 electrons
__has 23.42% C 9 character in a p3 hybrid
__has 76.58% O13 character in a p3 hybrid

14. A bonding orbital for C12-H14 with 0.9948 electrons
__has 62.39% C12 character in a sp2.79 hybrid
__has 37.61% H14 character in a s orbital

15. A bonding orbital for C12-H15 with 0.9779 electrons
__has 62.63% C12 character in a s0.94 p3 hybrid
__has 37.37% H15 character in a s orbital

16. A bonding orbital for C12-H16 with 0.9876 electrons
__has 62.83% C12 character in a sp2.80 hybrid
__has 37.17% H16 character in a s orbital

23. A lone pair orbital for O13 with 0.9903 electrons
__made from a sp0.76 hybrid

24. A lone pair orbital for O13 with 0.1154 electrons
__made from a p3 hybrid

-With core pairs on: C 1 C 2 C 6 C 9 C12 O13 -

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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, 6, for C2-H7 with the antibonding acceptor orbital, 172, for C6-C9 is 20.7 kJ/mol.

The interaction of bonding donor orbital, 8, for C6-C9 with the second lone pair acceptor orbital, 24, for O13 is 105. kJ/mol.

The interaction of bonding donor orbital, 11, for C9-C12 with the second lone pair acceptor orbital, 24, for O13 is 47.9 kJ/mol.

The interaction of bonding donor orbital, 15, for C12-H15 with the second antibonding acceptor orbital, 177, for C9-O13 is 27.4 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 ----- -3.096
27 ----- -3.116

26 ----- -3.781


25 ----- -8.388


24 -^--- -12.76

23 -^-v- -13.43

22 -^-v- -13.63

21 -^-v- -13.94


20 -^-v- -15.25
19 -^-v- -15.26
18 -^-v- -15.35

17 -^-v- -15.81

16 -^-v- -16.43

15 -^-v- -17.33

14 -^-v- -17.74

13 -^-v- -18.02


12 -^-v- -19.05


11 -^-v- -20.27


10 -^-v- -22.66


9 -^-v- -24.31


8 -^-v- -25.64


7 -^-v- -33.81


6 -^-v- -270.9


5 -^-v- -272.1

4 -^-v- -272.4

3 -^-v- -273.0


2 -^-v- -275.8


1 -^-v- -514.6

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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 = -271.5335127017 Hartrees

* The Lewis Structure (NBO analysis) calculations are done without diffuse functions to cut down on the size of the problem.

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