CH3CH2COCH3, 2-butanone

H6H7
\ /
H5 - C4
\
C3 - H8
/ \
O1 = C2H12H9
\ |
C10 - H11
/
H13
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=-0.519
C2 charge= 0.679
C3 charge=-0.059
C4 charge=-0.326
H5 charge= 0.096
H6 charge= 0.095
H7 charge= 0.097
H8 charge= 0.040
H9 charge= 0.042
C10 charge=-0.709
H11 charge= 0.178
H12 charge= 0.177
H13 charge= 0.207
with a dipole moment of 3.03449 Debye

Bond Lengths:

between O1 and C2: distance=1.230 ang___ between O1 and C3: distance=2.416 ang___
between O1 and C4: distance=2.838 ang___ between C2 and C3: distance=1.528 ang___
between C2 and C10: distance=1.523 ang___ between C2 and H13: distance=2.162 ang___
between C3 and C4: distance=1.534 ang___ between C3 and H8: distance=1.109 ang___
between C3 and H9: distance=1.110 ang___ between C3 and C10: distance=2.595 ang___
between C4 and H5: distance=1.103 ang___ between C4 and H6: distance=1.103 ang___
between C4 and H7: distance=1.103 ang___ between C10 and H11: distance=1.106 ang___
between C10 and H12: distance=1.106 ang___ between C10 and H13: distance=1.100 ang___

Bond Angles:

for C3-C2-O1: angle=121.9 deg___ for C4-C3-C2: angle=114.5 deg___
for H5-C4-C3: angle=110.9 deg___ for H6-C4-C3: angle=110.9 deg___
for H7-C4-C3: angle=110.6 deg___ for H8-C3-C2: angle=107.5 deg___
for H9-C3-C2: angle=106.9 deg___ for C10-C2-O1: angle=121.5 deg___
for H11-C10-C2: angle=109.9 deg___ for H12-C10-C2: angle=110.5 deg___
for H13-C10-C2: angle=109.9 deg___

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Bond Orders (Mulliken):

between O1 and C2: order=1.930___ between O1 and C3: order=-0.140___
between O1 and C4: order=0.059___ between C2 and C3: order=0.725___
between C2 and C10: order=0.738___ between C2 and H13: order=-0.065___
between C3 and C4: order=0.798___ between C3 and H8: order=1.001___
between C3 and H9: order=0.991___ between C3 and C10: order=-0.256___
between C4 and H5: order=0.979___ between C4 and H6: order=0.979___
between C4 and H7: order=0.997___ between C10 and H11: order=0.981___
between C10 and H12: order=0.994___ between C10 and H13: order=1.010___

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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.

Hybridization in the Best Lewis Structure

1. A bonding orbital for O1-C2 with 1.9972 electrons
__has 65.08% O 1 character in a sp1.43 hybrid
__has 34.92% C 2 character in a sp2.07 hybrid

2. A bonding orbital for O1-C2 with 1.9872 electrons
__has 70.50% O 1 character in a p-pi orbital ( 99.81% p 0.18% d)
__has 29.50% C 2 character in a p-pi orbital ( 99.40% p 0.60% d)

3. A bonding orbital for C2-C3 with 1.9898 electrons
__has 48.14% C 2 character in a sp1.94 hybrid
__has 51.86% C 3 character in a sp2.84 hybrid

4. A bonding orbital for C2-C10 with 1.9924 electrons
__has 48.47% C 2 character in a sp1.94 hybrid
__has 51.53% C10 character in a sp2.66 hybrid

5. A bonding orbital for C3-C4 with 1.9931 electrons
__has 52.00% C 3 character in a sp2.31 hybrid
__has 48.00% C 4 character in a sp2.52 hybrid

6. A bonding orbital for C3-H8 with 1.9740 electrons
__has 59.60% C 3 character in a s0.85 p3 hybrid
__has 40.40% H 8 character in a s orbital

7. A bonding orbital for C3-H9 with 1.9722 electrons
__has 59.65% C 3 character in a s0.84 p3 hybrid
__has 40.35% H 9 character in a s orbital

8. A bonding orbital for C4-H5 with 1.9916 electrons
__has 59.87% C 4 character in a s0.94 p3 hybrid
__has 40.13% H 5 character in a s orbital

9. A bonding orbital for C4-H6 with 1.9916 electrons
__has 59.72% C 4 character in a s0.94 p3 hybrid
__has 40.28% H 6 character in a s orbital

10. A bonding orbital for C4-H7 with 1.9911 electrons
__has 59.08% C 4 character in a s0.94 p3 hybrid
__has 40.92% H 7 character in a s orbital

11. A bonding orbital for C10-H11 with 1.9802 electrons
__has 60.01% C10 character in a s0.93 p3 hybrid
__has 39.99% H11 character in a s orbital

12. A bonding orbital for C10-H12 with 1.9818 electrons
__has 59.96% C10 character in a s0.94 p3 hybrid
__has 40.04% H12 character in a s orbital

13. A bonding orbital for C10-H13 with 1.9927 electrons
__has 60.89% C10 character in a sp2.95 hybrid
__has 39.11% H13 character in a s orbital

19. A lone pair orbital for O1 with 1.9780 electrons
__made from a sp0.69 hybrid

20. A lone pair orbital for O1 with 1.9156 electrons
__made from a p3 hybrid

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

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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 C3-H8 with the second antibonding acceptor orbital, 157, for O1-C2 is 25.6 kJ/mol.

The interaction of bonding donor orbital, 7, for C3-H9 with the second antibonding acceptor orbital, 157, for O1-C2 is 28.9 kJ/mol.

The interaction of bonding donor orbital, 11, for C10-H11 with the second antibonding acceptor orbital, 157, for O1-C2 is 26.7 kJ/mol.

The interaction of bonding donor orbital, 12, for C10-H12 with the second antibonding acceptor orbital, 157, for O1-C2 is 23.6 kJ/mol.

The interaction of the second lone pair donor orbital, 20, for O1 with the antibonding acceptor orbital, 158, for C2-C3 is 109. kJ/mol.

The interaction of the second lone pair donor orbital, 20, for O1 with the antibonding acceptor orbital, 159, for C2-C10 is 107. 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.

24 ----- 2.187

23 ----- 1.386

22 ----- 1.113


21 ----- -1.817


20 -^-v- -5.759


19 -^-v- -8.346

18 -^-v- -8.753
17 -^-v- -8.837

16 -^-v- -8.996

15 -^-v- -9.855

14 -^-v- -10.34

13 -^-v- -10.76

12 -^-v- -11.57

11 -^-v- -11.67


10 -^-v- -12.79


9 -^-v- -15.69


8 -^-v- -18.14


7 -^-v- -19.38


6 -^-v- -25.74


5 -^-v- -266.0

4 -^-v- -266.4

3 -^-v- -266.7


2 -^-v- -268.8


1 -^-v- -506.1

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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 = -232.5464817068 Hartrees

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