CH3CH2COCH3+•, 2-butanone radical cation

H9H7H6
\ \ /
O1C3 - C4
\\ / \ \
C2H8H5
|
C10 - H12
/ |
H13H11
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=-0.081
C2 charge= 0.483
C3 charge=-0.123
C4 charge=-0.301
H5 charge= 0.131
H6 charge= 0.205
H7 charge= 0.165
H8 charge= 0.152
H9 charge= 0.159
C10 charge=-0.500
H11 charge= 0.233
H12 charge= 0.224
H13 charge= 0.252
with a dipole moment of 12.34361 Debye

Bond Lengths:

between O1 and C2: distance=1.208 ang___ between C2 and C3: distance=1.609 ang___
between C2 and C10: distance=1.508 ang___ between C3 and C4: distance=1.519 ang___
between C3 and H8: distance=1.110 ang___ between C3 and H9: distance=1.102 ang___
between C3 and C10: distance=2.697 ang___ between C4 and H5: distance=1.101 ang___
between C4 and H6: distance=1.117 ang___ between C4 and H7: distance=1.105 ang___
between C10 and H11: distance=1.110 ang___ between C10 and H12: distance=1.103 ang___
between C10 and H13: distance=1.100 ang___

Bond Angles:

for C3-C2-O1: angle=114.7 deg___ for C4-C3-C2: angle=109.9 deg___
for H5-C4-C3: angle=114.3 deg___ for H6-C4-C3: angle=105.3 deg___
for H7-C4-C3: angle=113.3 deg___ for H8-C3-C2: angle=101.2 deg___
for H9-C3-C2: angle=106.7 deg___ for C10-C2-O1: angle=125.4 deg___
for H11-C10-C2: angle=106.2 deg___ for H12-C10-C2: angle=109.6 deg___
for H13-C10-C2: angle=110.2 deg___

Top of page.

Bond Orders (Mulliken):

between O1 and C2: order=1.582___ between C2 and C3: order=0.803___
between C2 and C10: order=0.799___ between C3 and C4: order=0.833___
between C3 and H8: order=0.917___ between C3 and H9: order=0.976___
between C3 and C10: order=-0.133___ between C4 and H5: order=0.978___
between C4 and H6: order=0.974___ between C4 and H7: order=0.939___
between C10 and H11: order=0.914___ between C10 and H12: order=0.945___
between C10 and H13: order=0.961___

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. 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 0.9988 electrons
__has 69.13% O 1 character in a sp1.45 hybrid
__has 30.87% C 2 character in a sp2.35 hybrid

2. A bonding orbital for O1-C2 with 0.9986 electrons
__has 84.81% O 1 character in a p3 hybrid
__has 15.19% C 2 character in a p3 hybrid

3. A bonding orbital for C2-C3 with 0.9932 electrons
__has 51.43% C 2 character in a sp2.05 hybrid
__has 48.57% C 3 character in a s0.76 p3 hybrid

4. A bonding orbital for C2-C10 with 0.9970 electrons
__has 50.69% C 2 character in a sp1.64 hybrid
__has 49.31% C10 character in a sp2.97 hybrid

5. A bonding orbital for C3-C4 with 0.9901 electrons
__has 54.08% C 3 character in a sp2.20 hybrid
__has 45.92% C 4 character in a sp2.61 hybrid

6. A bonding orbital for C3-H8 with 0.9873 electrons
__has 61.81% C 3 character in a s0.91 p3 hybrid
__has 38.19% H 8 character in a s orbital

7. A bonding orbital for C3-H9 with 0.9922 electrons
__has 62.59% C 3 character in a sp2.93 hybrid
__has 37.41% H 9 character in a s orbital

8. A bonding orbital for C4-H5 with 0.9957 electrons
__has 60.56% C 4 character in a sp2.93 hybrid
__has 39.44% H 5 character in a s orbital

9. A bonding orbital for C4-H6 with 0.9910 electrons
__has 61.60% C 4 character in a s0.85 p3 hybrid
__has 38.40% H 6 character in a s orbital

10. A bonding orbital for C4-H7 with 0.9952 electrons
__has 61.00% C 4 character in a s0.99 p3 hybrid
__has 39.00% H 7 character in a s orbital

11. A bonding orbital for C10-H11 with 0.9783 electrons
__has 63.54% C10 character in a s0.93 p3 hybrid
__has 36.46% H11 character in a s orbital

12. A bonding orbital for C10-H12 with 0.9874 electrons
__has 63.24% C10 character in a sp2.92 hybrid
__has 36.76% H12 character in a s orbital

13. A bonding orbital for C10-H13 with 0.9936 electrons
__has 63.18% C10 character in a sp2.87 hybrid
__has 36.82% H13 character in a s orbital

19. A lone pair orbital for O1 with 0.9912 electrons
__made from a sp0.69 hybrid

20. A lone pair orbital for O1 with 0.9757 electrons
__made from a p3 hybrid

-With core pairs on: O 1 C 2 C 3 C 4 C10 -

Up Electrons

1. A bonding orbital for O1-C2 with 0.9987 electrons
__has 65.47% O 1 character in a sp1.29 hybrid
__has 34.53% C 2 character in a sp2.38 hybrid

2. A bonding orbital for O1-C2 with 0.9974 electrons
__has 76.41% O 1 character in a p3 hybrid
__has 23.59% C 2 character in a p3 hybrid

3. A bonding orbital for C2-C3 with 0.9248 electrons
__has 61.33% C 2 character in a sp2.11 hybrid
__has 38.67% C 3 character in a s0.69 p3 hybrid

4. A bonding orbital for C2-C10 with 0.9652 electrons
__has 57.02% C 2 character in a sp1.57 hybrid
__has 42.98% C10 character in a s0.93 p3 hybrid

5. A bonding orbital for C3-C4 with 0.9876 electrons
__has 53.52% C 3 character in a sp2.13 hybrid
__has 46.48% C 4 character in a sp2.60 hybrid

6. A bonding orbital for C3-H8 with 0.9805 electrons
__has 61.63% C 3 character in a s0.93 p3 hybrid
__has 38.37% H 8 character in a s orbital

7. A bonding orbital for C3-H9 with 0.9930 electrons
__has 61.78% C 3 character in a sp2.90 hybrid
__has 38.22% H 9 character in a s orbital

8. A bonding orbital for C4-H5 with 0.9956 electrons
__has 60.59% C 4 character in a sp2.95 hybrid
__has 39.41% H 5 character in a s orbital

9. A bonding orbital for C4-H6 with 0.9849 electrons
__has 62.15% C 4 character in a s0.86 p3 hybrid
__has 37.85% H 6 character in a s orbital

10. A bonding orbital for C4-H7 with 0.9948 electrons
__has 61.16% C 4 character in a s0.98 p3 hybrid
__has 38.84% H 7 character in a s orbital

11. A bonding orbital for C10-H11 with 0.9785 electrons
__has 62.85% C10 character in a s0.95 p3 hybrid
__has 37.15% H11 character in a s orbital

12. A bonding orbital for C10-H12 with 0.9866 electrons
__has 62.76% C10 character in a sp2.86 hybrid
__has 37.24% H12 character in a s orbital

13. A bonding orbital for C10-H13 with 0.9945 electrons
__has 62.63% C10 character in a sp2.77 hybrid
__has 37.37% H13 character in a s orbital

19. A lone pair orbital for O1 with 0.9902 electrons
__made from a sp0.77 hybrid

20. A lone pair orbital for O1 with 0.1180 electrons
__made from a p3 hybrid

-With core pairs on: O 1 C 2 C 3 C 4 C10 -

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 C2-C3 with the second lone pair acceptor orbital, 20, for O1 is 114. kJ/mol.

The interaction of bonding donor orbital, 4, for C2-C10 with the second lone pair acceptor orbital, 20, for O1 is 42.0 kJ/mol.

The interaction of bonding donor orbital, 11, for C10-H11 with the second antibonding acceptor orbital, 157, for O1-C2 is 26.6 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. Only the spin up electron orbital energies are given.

24 ----- -3.270

23 ----- -3.449

22 ----- -3.975


21 ----- -8.768


20 -^--- -13.39

19 -^-v- -14.22

18 -^-v- -14.98

17 -^-v- -15.49

16 -^-v- -15.67
15 -^-v- -15.71

14 -^-v- -16.70


13 -^-v- -17.83

12 -^-v- -18.12

11 -^-v- -18.42


10 -^-v- -19.58


9 -^-v- -21.75


8 -^-v- -24.42


7 -^-v- -25.81


6 -^-v- -34.41


5 -^-v- -271.9

4 -^-v- -272.8

3 -^-v- -273.4


2 -^-v- -276.3


1 -^-v- -515.3

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 = -232.2064074279 Hartrees

Top of page.

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