2-dehydro-butane radical, CH3CH2CH(•)CH3

H4H6
\ |
H12H13C3 - H5
\ | /
C1 - C2
/ \
H10 - C8H7
| \
H11H9
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= 0.030
C2 charge=-0.105
C3 charge=-0.449
H4 charge= 0.128
H5 charge= 0.140
H6 charge= 0.134
H7 charge= 0.093
C8 charge=-0.439
H9 charge= 0.108
H10 charge= 0.117
H11 charge= 0.121
H12 charge= 0.051
H13 charge= 0.067
with a dipole moment of 0.36094 Debye

Bond Lengths:

between C1 and C2: distance=1.497 ang___ between C1 and C3: distance=2.611 ang___
between C1 and C8: distance=1.545 ang___ between C1 and H12: distance=1.118 ang___
between C1 and H13: distance=1.111 ang___ between C2 and C3: distance=1.496 ang___
between C2 and H4: distance=2.165 ang___ between C2 and H7: distance=1.098 ang___
between C2 and H13: distance=2.141 ang___ between C3 and H4: distance=1.109 ang___
between C3 and H5: distance=1.104 ang___ between C3 and H6: distance=1.116 ang___
between C8 and H9: distance=1.104 ang___ between C8 and H10: distance=1.104 ang___
between C8 and H11: distance=1.105 ang___

Bond Angles:

for C3-C2-C1: angle=121.4 deg___ for H4-C3-C2: angle=111.5 deg___
for H5-C3-C2: angle=112.1 deg___ for H6-C3-C2: angle=112.3 deg___
for H7-C2-C1: angle=118.2 deg___ for C8-C1-C2: angle=113.8 deg___
for H9-C8-C1: angle=110.8 deg___ for H10-C8-C1: angle=111.5 deg___
for H11-C8-C1: angle=110.8 deg___ for H12-C1-C2: angle=109.8 deg___
for H13-C1-C2: angle=109.4 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=0.723___ between C1 and C3: order=0.059___
between C1 and C8: order=0.807___ between C1 and H12: order=0.970___
between C1 and H13: order=1.030___ between C2 and C3: order=0.735___
between C2 and H4: order=-0.070___ between C2 and H7: order=0.893___
between C2 and H13: order=-0.085___ between C3 and H4: order=1.019___
between C3 and H5: order=1.001___ between C3 and H6: order=0.964___
between C8 and H9: order=0.989___ between C8 and H10: order=0.996___
between C8 and H11: 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 0.9957 electrons
__has 49.99% C 1 character in a sp2.51 hybrid
__has 50.01% C 2 character in a sp1.90 hybrid

2. A bonding orbital for C1-C8 with 0.9966 electrons
__has 50.49% C 1 character in a sp2.49 hybrid
__has 49.51% C 8 character in a sp2.43 hybrid

3. A bonding orbital for C1-H12 with 0.9945 electrons
__has 56.65% C 1 character in a s0.80 p3 hybrid
__has 43.35% H12 character in a s orbital

4. A bonding orbital for C1-H13 with 0.9926 electrons
__has 58.01% C 1 character in a s0.85 p3 hybrid
__has 41.99% H13 character in a s orbital

5. A bonding orbital for C2-C3 with 0.9969 electrons
__has 50.49% C 2 character in a sp1.88 hybrid
__has 49.51% C 3 character in a sp2.34 hybrid

6. A bonding orbital for C2-H7 with 0.9926 electrons
__has 60.25% C 2 character in a sp2.39 hybrid
__has 39.75% H 7 character in a s orbital

7. A bonding orbital for C3-H4 with 0.9965 electrons
__has 58.37% C 3 character in a s0.93 p3 hybrid
__has 41.63% H 4 character in a s orbital

8. A bonding orbital for C3-H5 with 0.9964 electrons
__has 59.08% C 3 character in a s0.94 p3 hybrid
__has 40.92% H 5 character in a s orbital

9. A bonding orbital for C3-H6 with 0.9984 electrons
__has 57.03% C 3 character in a s0.88 p3 hybrid
__has 42.97% H 6 character in a s orbital

10. A bonding orbital for C8-H9 with 0.9962 electrons
__has 59.14% C 8 character in a s0.93 p3 hybrid
__has 40.86% H 9 character in a s orbital

11. A bonding orbital for C8-H10 with 0.9962 electrons
__has 59.19% C 8 character in a s0.93 p3 hybrid
__has 40.81% H10 character in a s orbital

12. A bonding orbital for C8-H11 with 0.9961 electrons
__has 59.00% C 8 character in a s0.92 p3 hybrid
__has 41.00% H11 character in a s orbital

17. A lone pair orbital for C2 with 0.9479 electrons
__made from a s0.05 p3 hybrid

-With core pairs on: C 1 C 2 C 3 C 8 -

Up Electrons

1. A bonding orbital for C1-C2 with 0.9955 electrons
__has 54.97% C 1 character in a sp2.38 hybrid
__has 45.03% C 2 character in a sp1.88 hybrid

2. A bonding orbital for C1-C8 with 0.9958 electrons
__has 51.28% C 1 character in a sp2.57 hybrid
__has 48.72% C 8 character in a sp2.46 hybrid

3. A bonding orbital for C1-H12 with 0.9809 electrons
__has 61.17% C 1 character in a s0.81 p3 hybrid
__has 38.83% H12 character in a s orbital

4. A bonding orbital for C1-H13 with 0.9886 electrons
__has 59.89% C 1 character in a s0.82 p3 hybrid
__has 40.11% H13 character in a s orbital

5. A bonding orbital for C2-C3 with 0.9971 electrons
__has 45.52% C 2 character in a sp1.86 hybrid
__has 54.48% C 3 character in a sp2.23 hybrid

6. A bonding orbital for C2-H7 with 0.9938 electrons
__has 54.72% C 2 character in a sp2.31 hybrid
__has 45.28% H 7 character in a s orbital

7. A bonding orbital for C3-H4 with 0.9923 electrons
__has 60.32% C 3 character in a s0.89 p3 hybrid
__has 39.68% H 4 character in a s orbital

8. A bonding orbital for C3-H5 with 0.9947 electrons
__has 60.06% C 3 character in a s0.91 p3 hybrid
__has 39.94% H 5 character in a s orbital

9. A bonding orbital for C3-H6 with 0.9847 electrons
__has 61.69% C 3 character in a s0.89 p3 hybrid
__has 38.31% H 6 character in a s orbital

10. A bonding orbital for C8-H9 with 0.9964 electrons
__has 59.01% C 8 character in a s0.93 p3 hybrid
__has 40.99% H 9 character in a s orbital

11. A bonding orbital for C8-H10 with 0.9966 electrons
__has 59.05% C 8 character in a s0.94 p3 hybrid
__has 40.95% H10 character in a s orbital

12. A bonding orbital for C8-H11 with 0.9962 electrons
__has 58.84% C 8 character in a s0.92 p3 hybrid
__has 41.16% H11 character in a s orbital

-With core pairs on: C 1 C 2 C 3 C 8 -

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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 C1-H12 with the lone pair acceptor orbital, 17, for C2 is 29.2 kJ/mol.

The interaction of bonding donor orbital, 9, for C3-H6 with the lone pair acceptor orbital, 17, for C2 is 27.6 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.

21 ----- 2.457

20 ----- 2.143

19 ----- 1.721

18 ----- 1.351


17 -^--- -3.919


16 -^-v- -8.084
15 -^-v- -8.130

14 -^-v- -8.450

13 -^-v- -8.930

12 -^-v- -9.749

11 -^-v- -10.47
10 -^-v- -10.52

9 -^-v- -11.04


8 -^-v- -13.66


7 -^-v- -15.38


6 -^-v- -17.76


5 -^-v- -19.46


4 -^-v- -265.9

3 -^-v- -266.0

2 -^-v- -266.2

1 -^-v- -266.4

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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 = -157.8327933656 Hartrees

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