CH3CH2CH2COCH3, 2-pentanone

H6H8
\ |
C5H9
/ \ /
H7H11C4
\ | \
C3H10
/ \
O1 = C2H14H12
\ |
C13
/ \
H16H15
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=-0.184
C2 charge= 0.555
C3 charge=-0.303
C4 charge= 0.070
C5 charge=-0.390
H6 charge= 0.170
H7 charge= 0.183
H8 charge= 0.187
H9 charge= 0.142
H10 charge= 0.087
H11 charge= 0.184
H12 charge= 0.143
C13 charge=-0.524
H14 charge= 0.210
H15 charge= 0.232
H16 charge= 0.236
with a dipole moment of 10.03676 Debye

Bond Lengths:

between O1 and C2: distance=1.225 ang___ between O1 and C3: distance=2.429 ang___
between C2 and C3: distance=1.550 ang___ between C2 and C4: distance=2.557 ang___
between C2 and C13: distance=1.518 ang___ between C2 and H16: distance=2.168 ang___
between C3 and C4: distance=1.526 ang___ between C3 and C5: distance=2.551 ang___
between C3 and H11: distance=1.114 ang___ between C3 and H12: distance=1.104 ang___
between C3 and C13: distance=2.631 ang___ between C4 and C5: distance=1.508 ang___
between C4 and H7: distance=2.149 ang___ between C4 and H9: distance=1.122 ang___
between C4 and H10: distance=1.107 ang___ between C5 and H6: distance=1.105 ang___
between C5 and H7: distance=1.145 ang___ between C5 and H8: distance=1.103 ang___
between C5 and H10: distance=2.177 ang___ between C13 and H14: distance=1.105 ang___
between C13 and H15: distance=1.108 ang___ between C13 and H16: distance=1.099 ang___

Bond Angles:

for C3-C2-O1: angle=121.6 deg___ for C4-C3-C2: angle=112.4 deg___
for C5-C4-C3: angle=114.4 deg___ for H6-C5-C4: angle=114.3 deg___
for H7-C5-C4: angle=107.3 deg___ for H8-C5-C4: angle=114.0 deg___
for H9-C4-C3: angle=105.5 deg___ for H10-C4-C3: angle=110.9 deg___
for H11-C3-C2: angle=102.5 deg___ for H12-C3-C2: angle=107.8 deg___
for C13-C2-O1: angle=120.3 deg___ for H14-C13-C2: angle=108.8 deg___
for H15-C13-C2: angle=107.0 deg___ for H16-C13-C2: angle=110.8 deg___

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Bond Orders (Mulliken):

between O1 and C2: order=1.414___ between O1 and C3: order=-0.054___
between C2 and C3: order=0.652___ between C2 and C4: order=-0.086___
between C2 and C13: order=0.680___ between C2 and H16: order=-0.057___
between C3 and C4: order=1.004___ between C3 and C5: order=-0.104___
between C3 and H11: order=0.950___ between C3 and H12: order=0.953___
between C3 and C13: order=-0.109___ between C4 and C5: order=0.680___
between C4 and H7: order=-0.075___ between C4 and H9: order=0.927___
between C4 and H10: order=0.993___ between C5 and H6: order=0.952___
between C5 and H7: order=1.004___ between C5 and H8: order=0.963___
between C5 and H10: order=-0.075___ between C13 and H14: order=0.945___
between C13 and H15: order=0.923___ between C13 and H16: order=0.998___

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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 O1-C2 with 0.9970 electrons
__has 69.43% O 1 character in a sp1.65 hybrid
__has 30.57% C 2 character in a sp2.49 hybrid

2. A bonding orbital for O1-C2 with 0.9974 electrons
__has 85.17% O 1 character in a p3 hybrid
__has 14.83% C 2 character in a p3 hybrid

3. A bonding orbital for C2-C3 with 0.9944 electrons
__has 51.30% C 2 character in a sp1.81 hybrid
__has 48.70% C 3 character in a s0.86 p3 hybrid

4. A bonding orbital for C2-C13 with 0.9965 electrons
__has 50.47% C 2 character in a sp1.84 hybrid
__has 49.53% C13 character in a sp2.92 hybrid

5. A bonding orbital for C3-C4 with 0.9926 electrons
__has 53.98% C 3 character in a sp2.21 hybrid
__has 46.02% C 4 character in a sp2.82 hybrid

6. A bonding orbital for C3-H11 with 0.9757 electrons
__has 62.67% C 3 character in a s0.85 p3 hybrid
__has 37.33% H11 character in a s orbital

7. A bonding orbital for C3-H12 with 0.9883 electrons
__has 62.51% C 3 character in a s0.97 p3 hybrid
__has 37.49% H12 character in a s orbital

8. A bonding orbital for C4-C5 with 0.9966 electrons
__has 51.85% C 4 character in a sp2.31 hybrid
__has 48.15% C 5 character in a sp2.40 hybrid

9. A bonding orbital for C4-H9 with 0.9890 electrons
__has 60.92% C 4 character in a s0.79 p3 hybrid
__has 39.08% H 9 character in a s orbital

10. A bonding orbital for C4-H10 with 0.9916 electrons
__has 60.43% C 4 character in a s0.89 p3 hybrid
__has 39.57% H10 character in a s orbital

11. A bonding orbital for C5-H6 with 0.9957 electrons
__has 60.40% C 5 character in a s0.97 p3 hybrid
__has 39.60% H 6 character in a s orbital

12. A bonding orbital for C5-H7 with 0.9947 electrons
__has 59.50% C 5 character in a s0.79 p3 hybrid
__has 40.50% H 7 character in a s orbital

13. A bonding orbital for C5-H8 with 0.9949 electrons
__has 61.63% C 5 character in a sp2.94 hybrid
__has 38.37% H 8 character in a s orbital

14. A bonding orbital for C13-H14 with 0.9857 electrons
__has 63.09% C13 character in a s0.98 p3 hybrid
__has 36.91% H14 character in a s orbital

15. A bonding orbital for C13-H15 with 0.9805 electrons
__has 63.32% C13 character in a s0.94 p3 hybrid
__has 36.68% H15 character in a s orbital

16. A bonding orbital for C13-H16 with 0.9950 electrons
__has 62.98% C13 character in a sp2.84 hybrid
__has 37.02% H16 character in a s orbital

23. A lone pair orbital for O1 with 0.9904 electrons
__made from a sp0.63 hybrid

24. A lone pair orbital for O1 with 0.9767 electrons
__made from a p3 hybrid

-With core pairs on: O 1 C 2 C 3 C 4 C 5 C13 -

Up Electrons

1. A bonding orbital for O1-C2 with 0.9983 electrons
__has 65.12% O 1 character in a sp1.39 hybrid
__has 34.88% C 2 character in a sp2.39 hybrid

2. A bonding orbital for O1-C2 with 0.9970 electrons
__has 77.60% O 1 character in a p3 hybrid
__has 22.40% C 2 character in a p3 hybrid

3. A bonding orbital for C2-C3 with 0.9560 electrons
__has 58.11% C 2 character in a sp1.84 hybrid
__has 41.89% C 3 character in a s0.80 p3 hybrid

4. A bonding orbital for C2-C13 with 0.9597 electrons
__has 57.06% C 2 character in a sp1.79 hybrid
__has 42.94% C13 character in a s0.95 p3 hybrid

5. A bonding orbital for C3-C4 with 0.9921 electrons
__has 53.38% C 3 character in a sp2.17 hybrid
__has 46.62% C 4 character in a sp2.81 hybrid

6. A bonding orbital for C3-H11 with 0.9760 electrons
__has 62.02% C 3 character in a s0.87 p3 hybrid
__has 37.98% H11 character in a s orbital

7. A bonding orbital for C3-H12 with 0.9869 electrons
__has 62.16% C 3 character in a s0.99 p3 hybrid
__has 37.84% H12 character in a s orbital

8. A bonding orbital for C4-C5 with 0.9961 electrons
__has 52.18% C 4 character in a sp2.30 hybrid
__has 47.82% C 5 character in a sp2.38 hybrid

9. A bonding orbital for C4-H9 with 0.9818 electrons
__has 61.38% C 4 character in a s0.79 p3 hybrid
__has 38.62% H 9 character in a s orbital

10. A bonding orbital for C4-H10 with 0.9911 electrons
__has 60.56% C 4 character in a s0.89 p3 hybrid
__has 39.44% H10 character in a s orbital

11. A bonding orbital for C5-H6 with 0.9948 electrons
__has 60.17% C 5 character in a s0.99 p3 hybrid
__has 39.83% H 6 character in a s orbital

12. A bonding orbital for C5-H7 with 0.9669 electrons
__has 56.73% C 5 character in a s0.75 p3 hybrid
__has 43.27% H 7 character in a s orbital

13. A bonding orbital for C5-H8 with 0.9926 electrons
__has 61.63% C 5 character in a sp2.87 hybrid
__has 38.37% H 8 character in a s orbital

14. A bonding orbital for C13-H14 with 0.9840 electrons
__has 62.71% C13 character in a sp2.95 hybrid
__has 37.29% H14 character in a s orbital

15. A bonding orbital for C13-H15 with 0.9800 electrons
__has 62.69% C13 character in a s0.96 p3 hybrid
__has 37.31% H15 character in a s orbital

16. A bonding orbital for C13-H16 with 0.9958 electrons
__has 62.37% C13 character in a sp2.78 hybrid
__has 37.63% H16 character in a s orbital

23. A lone pair orbital for O1 with 0.9893 electrons
__made from a sp0.72 hybrid

24. A lone pair orbital for O1 with 0.1177 electrons
__made from a p3 hybrid

-With core pairs on: O 1 C 2 C 3 C 4 C 5 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, 3, for C2-C3 with the second lone pair acceptor orbital, 24, for O1 is 56.3 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-C13 with the second lone pair acceptor orbital, 24, for O1 is 56.1 kJ/mol.

The interaction of bonding donor orbital, 6, for C3-H11 with the second antibonding acceptor orbital, 190, for O1-C2 is 25.6 kJ/mol.

The interaction of bonding donor orbital, 12, for C5-H7 with the second lone pair acceptor orbital, 24, for O1 is 29.2 kJ/mol.

The interaction of bonding donor orbital, 15, for C13-H15 with the second antibonding acceptor orbital, 190, for O1-C2 is 25.2 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 ----- -2.553

27 ----- -3.135

26 ----- -3.640


25 ----- -8.188


24 -^--- -12.37


23 -^-v- -13.48

22 -^-v- -13.98

21 -^-v- -14.24

20 -^-v- -14.76

19 -^-v- -15.04

18 -^-v- -15.27

17 -^-v- -15.90

16 -^-v- -16.16

15 -^-v- -17.05

14 -^-v- -17.56

13 -^-v- -17.99


12 -^-v- -19.05


11 -^-v- -20.32


10 -^-v- -22.57


9 -^-v- -24.31


8 -^-v- -25.56


7 -^-v- -33.41


6 -^-v- -271.3

5 -^-v- -271.9

4 -^-v- -272.1

3 -^-v- -272.7


2 -^-v- -275.5


1 -^-v- -514.3

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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 = -271.5406887681 Hartrees

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