(CH3)2CHCH2O•, 2-methylpropoxy radical, O-dehydro-2methylpropanol radical

H10H11
\ |
H6H7C3 - H12
\ | /
C1 - C2H14
/ | \ |
H8H9C4 - H13
/
O5
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=-0.470
C2 charge= 0.337
C3 charge=-0.693
C4 charge= 0.257
O5 charge=-0.393
H6 charge= 0.116
H7 charge= 0.128
H8 charge= 0.111
H9 charge= 0.008
H10 charge= 0.195
H11 charge= 0.151
H12 charge= 0.153
H13 charge= 0.026
H14 charge= 0.072
with a dipole moment of 2.50551 Debye

Bond Lengths:

between C1 and C2: distance=1.540 ang___ between C1 and C3: distance=2.558 ang___
between C1 and C4: distance=2.534 ang___ between C1 and H6: distance=1.104 ang___
between C1 and H7: distance=1.107 ang___ between C1 and H8: distance=1.104 ang___
between C2 and C3: distance=1.541 ang___ between C2 and C4: distance=1.548 ang___
between C2 and O5: distance=2.490 ang___ between C2 and H9: distance=1.110 ang___
between C3 and C4: distance=2.538 ang___ between C3 and H10: distance=1.104 ang___
between C3 and H11: distance=1.107 ang___ between C3 and H12: distance=1.106 ang___
between C4 and O5: distance=1.356 ang___ between C4 and H13: distance=1.129 ang___
between C4 and H14: distance=1.136 ang___

Bond Angles:

for C3-C2-C1: angle=112.2 deg___ for C4-C2-C1: angle=110.3 deg___
for O5-C4-C2: angle=117.9 deg___ for H6-C1-C2: angle=111.4 deg___
for H7-C1-C2: angle=110.7 deg___ for H8-C1-C2: angle=110.3 deg___
for H9-C2-C1: angle=108.4 deg___ for H10-C3-C2: angle=110.8 deg___
for H11-C3-C2: angle=110.9 deg___ for H12-C3-C2: angle=112.0 deg___
for H13-C4-C2: angle=112.1 deg___ for H14-C4-C2: angle=109.4 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=0.926___ between C1 and C3: order=-0.115___
between C1 and C4: order=-0.123___ between C1 and H6: order=0.976___
between C1 and H7: order=0.973___ between C1 and H8: order=0.981___
between C2 and C3: order=0.888___ between C2 and C4: order=0.973___
between C2 and O5: order=-0.080___ between C2 and H9: order=0.929___
between C3 and C4: order=-0.060___ between C3 and H10: order=0.982___
between C3 and H11: order=0.979___ between C3 and H12: order=0.972___
between C4 and O5: order=0.909___ between C4 and H13: order=0.951___
between C4 and H14: order=0.982___

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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 0.9945 electrons
__has 48.30% C 1 character in a sp2.51 hybrid
__has 51.70% C 2 character in a sp2.65 hybrid

2. A bonding orbital for C1-H6 with 0.9961 electrons
__has 59.30% C 1 character in a s0.95 p3 hybrid
__has 40.70% H 6 character in a s orbital

3. A bonding orbital for C1-H7 with 0.9962 electrons
__has 59.13% C 1 character in a s0.93 p3 hybrid
__has 40.87% H 7 character in a s orbital

4. A bonding orbital for C1-H8 with 0.9959 electrons
__has 59.71% C 1 character in a s0.94 p3 hybrid
__has 40.29% H 8 character in a s orbital

5. A bonding orbital for C2-C3 with 0.9941 electrons
__has 51.66% C 2 character in a sp2.62 hybrid
__has 48.34% C 3 character in a sp2.47 hybrid

6. A bonding orbital for C2-C4 with 0.9948 electrons
__has 51.31% C 2 character in a s0.99 p3 hybrid
__has 48.69% C 4 character in a sp2.17 hybrid

7. A bonding orbital for C2-H9 with 0.9875 electrons
__has 59.22% C 2 character in a s0.77 p3 hybrid
__has 40.78% H 9 character in a s orbital

8. A bonding orbital for C3-H10 with 0.9959 electrons
__has 59.48% C 3 character in a s0.93 p3 hybrid
__has 40.52% H10 character in a s orbital

9. A bonding orbital for C3-H11 with 0.9962 electrons
__has 59.22% C 3 character in a s0.93 p3 hybrid
__has 40.78% H11 character in a s orbital

10. A bonding orbital for C3-H12 with 0.9962 electrons
__has 59.37% C 3 character in a s0.94 p3 hybrid
__has 40.63% H12 character in a s orbital

11. A bonding orbital for C4-O5 with 0.9985 electrons
__has 33.87% C 4 character in a s0.99 p3 hybrid
__has 66.13% O 5 character in a sp2.29 hybrid

12. A bonding orbital for C4-H13 with 0.9953 electrons
__has 56.69% C 4 character in a s0.89 p3 hybrid
__has 43.31% H13 character in a s orbital

13. A bonding orbital for C4-H14 with 0.9947 electrons
__has 56.38% C 4 character in a s0.80 p3 hybrid
__has 43.62% H14 character in a s orbital

19. A lone pair orbital for O5 with 0.9959 electrons
__made from a sp0.43 hybrid

20. A lone pair orbital for O5 with 0.9820 electrons
__made from a p3 hybrid

21. A lone pair orbital for O5 with 0.9776 electrons
__made from a p3 hybrid

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

Up Electrons

1. A bonding orbital for C1-C2 with 0.9945 electrons
__has 48.63% C 1 character in a sp2.49 hybrid
__has 51.37% C 2 character in a sp2.59 hybrid

2. A bonding orbital for C1-H6 with 0.9957 electrons
__has 59.29% C 1 character in a s0.94 p3 hybrid
__has 40.71% H 6 character in a s orbital

3. A bonding orbital for C1-H7 with 0.9961 electrons
__has 59.18% C 1 character in a s0.93 p3 hybrid
__has 40.82% H 7 character in a s orbital

4. A bonding orbital for C1-H8 with 0.9957 electrons
__has 59.66% C 1 character in a s0.94 p3 hybrid
__has 40.34% H 8 character in a s orbital

5. A bonding orbital for C2-C3 with 0.9935 electrons
__has 51.59% C 2 character in a sp2.52 hybrid
__has 48.41% C 3 character in a sp2.47 hybrid

6. A bonding orbital for C2-C4 with 0.9797 electrons
__has 46.57% C 2 character in a s0.91 p3 hybrid
__has 53.43% C 4 character in a sp2.15 hybrid

7. A bonding orbital for C2-H9 with 0.9878 electrons
__has 58.79% C 2 character in a s0.78 p3 hybrid
__has 41.21% H 9 character in a s orbital

8. A bonding orbital for C3-H10 with 0.9949 electrons
__has 59.56% C 3 character in a s0.94 p3 hybrid
__has 40.44% H10 character in a s orbital

9. A bonding orbital for C3-H11 with 0.9962 electrons
__has 59.23% C 3 character in a s0.92 p3 hybrid
__has 40.77% H11 character in a s orbital

10. A bonding orbital for C3-H12 with 0.9962 electrons
__has 59.38% C 3 character in a s0.93 p3 hybrid
__has 40.62% H12 character in a s orbital

11. A bonding orbital for C4-O5 with 0.9982 electrons
__has 38.16% C 4 character in a sp2.96 hybrid
__has 61.84% O 5 character in a sp2.06 hybrid

12. A bonding orbital for C4-H13 with 0.9845 electrons
__has 59.49% C 4 character in a s0.88 p3 hybrid
__has 40.51% H13 character in a s orbital

13. A bonding orbital for C4-H14 with 0.9909 electrons
__has 57.47% C 4 character in a s0.78 p3 hybrid
__has 42.53% H14 character in a s orbital

19. A lone pair orbital for O5 with 0.9954 electrons
__made from a sp0.48 hybrid

20. A lone pair orbital for O5 with 0.9737 electrons
__made from a p3 hybrid

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

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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-C4 with the third lone pair acceptor orbital, 21, for O5 is 22.0 kJ/mol.

The interaction of the second lone pair donor orbital, 20, for O5 with the antibonding acceptor orbital, 173, for C4-H13 is 21.0 kJ/mol.

The interaction of the second lone pair donor orbital, 20, for O5 with the antibonding acceptor orbital, 174, for C4-H14 is 33.8 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.

25 ----- 1.939
24 ----- 1.782

23 ----- 1.409
22 ----- 1.271


21 -^--- -6.340

20 -^-v- -7.115


19 -^-v- -8.188

18 -^-v- -8.392

17 -^-v- -8.867

16 -^-v- -9.358

15 -^-v- -9.683

14 -^-v- -10.58

13 -^-v- -11.09

12 -^-v- -11.24

11 -^-v- -12.11


10 -^-v- -14.07


9 -^-v- -16.29

8 -^-v- -16.88


7 -^-v- -19.80


6 -^-v- -25.28


5 -^-v- -266.0

4 -^-v- -266.2

3 -^-v- -266.7


2 -^-v- -268.0


1 -^-v- -507.2

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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 = -233.0735067897 Hartrees

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