CH2=CH-CHOH., allylalcohol radical

H9H3
\ /
C1 - C2
// \
H8 - C5H4
\
O6
/
H7
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=-0.151
C2 charge=-0.383
H3 charge= 0.151
H4 charge= 0.179
C5 charge=-0.032
O6 charge=-0.430
H7 charge= 0.409
H8 charge= 0.115
H9 charge= 0.141
with a dipole moment of 2.38557 Debye

Bond Lengths:

between C1 and C2: distance=1.390 ang___ between C1 and H4: distance=2.169 ang___
between C1 and C5: distance=1.396 ang___ between C1 and O6: distance=2.406 ang___
between C1 and H9: distance=1.098 ang___ between C2 and H3: distance=1.093 ang___
between C2 and H4: distance=1.095 ang___ between C2 and C5: distance=2.482 ang___
between C2 and O6: distance=2.908 ang___ between C5 and O6: distance=1.378 ang___
between C5 and H8: distance=1.095 ang___ between O6 and H7: distance=0.974 ang___

Bond Angles:

for H3-C2-C1: angle=120.6 deg___ for H4-C2-C1: angle=121.1 deg___
for C5-C1-C2: angle=125.9 deg___ for O6-C5-C1: angle=120.2 deg___
for H7-O6-C5: angle=109.4 deg___ for H8-C5-C1: angle=122.6 deg___
for H9-C1-C2: angle=119.2 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=1.167___ between C1 and H4: order=-0.059___
between C1 and C5: order=1.247___ between C1 and O6: order=-0.191___
between C1 and H9: order=0.937___ between C2 and H3: order=0.969___
between C2 and H4: order=0.973___ between C2 and C5: order=0.224___
between C2 and O6: order=0.055___ between C5 and O6: order=0.982___
between C5 and H8: order=0.988___ between O6 and H7: order=0.851___

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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. Please note that your structure can't be well described by a single Lewis structure, because of extensive delocalization.

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 0.9962 electrons
__has 49.80% C 1 character in a sp1.64 hybrid
__has 50.20% C 2 character in a sp1.59 hybrid

2. A bonding orbital for C1-C5 with 0.9953 electrons
__has 48.04% C 1 character in a sp1.91 hybrid
__has 51.96% C 5 character in a sp1.38 hybrid

3. A bonding orbital for C1-H9 with 0.9889 electrons
__has 58.08% C 1 character in a sp2.57 hybrid
__has 41.92% H 9 character in a s orbital

4. A bonding orbital for C2-H3 with 0.9944 electrons
__has 60.60% C 2 character in a sp2.26 hybrid
__has 39.40% H 3 character in a s orbital

5. A bonding orbital for C2-H4 with 0.9943 electrons
__has 61.21% C 2 character in a sp2.23 hybrid
__has 38.79% H 4 character in a s orbital

6. A bonding orbital for C5-O6 with 0.9979 electrons
__has 33.46% C 5 character in a sp2.74 hybrid
__has 66.54% O 6 character in a sp2.21 hybrid

7. A bonding orbital for C5-H8 with 0.9935 electrons
__has 59.85% C 5 character in a sp2.14 hybrid
__has 40.15% H 8 character in a s orbital

8. A bonding orbital for O6-H7 with 0.9950 electrons
__has 74.12% O 6 character in a s0.81 p3 hybrid
__has 25.88% H 7 character in a s orbital

13. A lone pair orbital for C1 with 0.3132 electrons
__made from a p-pi orbital ( 99.94% p 0.06% d)

14. A lone pair orbital for C2 with 0.8583 electrons
__made from a p-pi orbital ( 99.97% p)

15. A lone pair orbital for C5 with 0.8298 electrons
__made from a p-pi orbital ( 99.96% p)

16. A lone pair orbital for O6 with 0.9930 electrons
__made from a sp1.09 hybrid

17. A lone pair orbital for O6 with 0.9876 electrons
__made from a p-pi orbital ( 99.95% p)

-With core pairs on: C 1 C 2 C 5 O 6 -

Up Electrons

1. A bonding orbital for C1-C2 with 0.9958 electrons
__has 54.61% C 1 character in a sp1.61 hybrid
__has 45.39% C 2 character in a sp1.64 hybrid

2. A bonding orbital for C1-C2 with 0.8921 electrons
__has 83.93% C 1 character in a p-pi orbital ( 99.98% p)
__has 16.07% C 2 character in a p-pi orbital ( 99.78% p 0.22% d)

3. A bonding orbital for C1-C5 with 0.9949 electrons
__has 53.07% C 1 character in a sp1.87 hybrid
__has 46.93% C 5 character in a sp1.46 hybrid

4. A bonding orbital for C1-H9 with 0.9887 electrons
__has 60.96% C 1 character in a sp2.68 hybrid
__has 39.04% H 9 character in a s orbital

5. A bonding orbital for C2-H3 with 0.9951 electrons
__has 56.31% C 2 character in a sp2.23 hybrid
__has 43.69% H 3 character in a s orbital

6. A bonding orbital for C2-H4 with 0.9948 electrons
__has 57.04% C 2 character in a sp2.19 hybrid
__has 42.96% H 4 character in a s orbital

7. A bonding orbital for C5-O6 with 0.9982 electrons
__has 31.45% C 5 character in a sp2.58 hybrid
__has 68.55% O 6 character in a sp1.99 hybrid

8. A bonding orbital for C5-H8 with 0.9946 electrons
__has 55.36% C 5 character in a sp2.13 hybrid
__has 44.64% H 8 character in a s orbital

9. A bonding orbital for O6-H7 with 0.9948 electrons
__has 73.81% O 6 character in a s0.81 p3 hybrid
__has 26.19% H 7 character in a s orbital

14. A lone pair orbital for C5 with 0.1768 electrons
__made from a p-pi orbital ( 99.87% p 0.13% d)

15. A lone pair orbital for O6 with 0.9924 electrons
__made from a sp1.20 hybrid

16. A lone pair orbital for O6 with 0.9288 electrons
__made from a p-pi orbital ( 99.93% p 0.07% d)

-With core pairs on: C 1 C 2 C 5 O 6 -

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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 the second bonding donor orbital, 2, for C1-C2 with the lone pair acceptor orbital, 14, for C5 is 220. kJ/mol.

The interaction of lone pair donor orbital, 14, for C5 with the second antibonding acceptor orbital, 119, for C1-C2 is 21.7 kJ/mol.

The interaction of the second lone pair donor orbital, 16, for O6 with the lone pair acceptor orbital, 14, for C5 is 159. 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.

20 ----- 2.387

19 ----- 1.799

18 ----- 0.184
17 ----- 0.172


16 -^--- -3.890


15 -^-v- -6.965


14 -^-v- -8.677

13 -^-v- -8.805


12 -^-v- -9.870

11 -^-v- -10.26


10 -^-v- -11.37


9 -^-v- -13.05


8 -^-v- -14.33


7 -^-v- -16.50


6 -^-v- -19.26


5 -^-v- -26.58


4 -^-v- -266.0

3 -^-v- -266.2


2 -^-v- -268.0


1 -^-v- -507.6

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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 = -192.5533171860 Hartrees

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