CH2=CHOLi, lithium salt of vinyl alcohol

H3H7
\ /
C1 = C2
/ \
H4O5
/
LI6
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=-1.349
C2 charge= 0.663
H3 charge= 0.356
H4 charge= 0.344
O5 charge=-0.783
LI6 charge= 0.780
H7 charge=-0.013
with a dipole moment of 4.93816 Debye

Bond Lengths:

between C1 and C2: distance=1.390 ang___ between C1 and H3: distance=1.092 ang___
between C1 and H4: distance=1.103 ang___ between C1 and O5: distance=2.385 ang___
between C1 and LI6: distance=2.289 ang___ between C1 and H7: distance=2.156 ang___
between C2 and O5: distance=1.310 ang___ between C2 and LI6: distance=2.174 ang___
between C2 and H7: distance=1.114 ang___ between O5 and LI6: distance=1.823 ang___

Bond Angles:

for H3-C1-C2: angle=121.1 deg___ for H4-C1-C2: angle=119.4 deg___
for O5-C2-C1: angle=124.1 deg___ for LI6-C2-C1: angle=76.42 deg___
for H7-C2-C1: angle=118.4 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=1.607___ between C1 and H3: order=0.959___
between C1 and H4: order=0.947___ between C1 and O5: order=-0.071___
between C1 and LI6: order=0.234___ between C1 and H7: order=-0.064___
between C2 and O5: order=1.178___ between C2 and LI6: order=0.147___
between C2 and H7: order=1.012___ between O5 and LI6: order=0.430___

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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.

Hybridization in the Best Lewis Structure

1. A bonding orbital for C1-C2 with 1.9966 electrons
__has 49.84% C 1 character in a sp1.70 hybrid
__has 50.16% C 2 character in a sp1.46 hybrid

2. A bonding orbital for C1-C2 with 1.9672 electrons
__has 69.31% C 1 character in a p3 hybrid
__has 30.69% C 2 character in a p3 hybrid

3. A bonding orbital for C1-H3 with 1.9890 electrons
__has 60.17% C 1 character in a sp2.13 hybrid
__has 39.83% H 3 character in a s orbital

4. A bonding orbital for C1-H4 with 1.9843 electrons
__has 58.69% C 1 character in a sp2.27 hybrid
__has 41.31% H 4 character in a s orbital

5. A bonding orbital for C2-O5 with 1.9966 electrons
__has 36.19% C 2 character in a sp2.23 hybrid
__has 63.81% O 5 character in a sp1.92 hybrid

6. A bonding orbital for C2-H7 with 1.9822 electrons
__has 57.53% C 2 character in a sp2.45 hybrid
__has 42.47% H 7 character in a s orbital

11. A lone pair orbital for O5 with 1.9750 electrons
__made from a sp0.54 hybrid

12. A lone pair orbital for O5 with 1.9293 electrons
__made from a p3 hybrid

13. A lone pair orbital for O5 with 1.7619 electrons
__made from a p3 hybrid

109. A antibonding orbital for C1-C2 with 0.2238 electrons
__has 30.69% C 1 character in a p3 hybrid
__has 69.31% C 2 character in a p3 hybrid

-With core pairs on: C 1 C 2 O 5 Li 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 bonding donor orbital, 3, for C1-H3 with the antibonding acceptor orbital, 112, for C2-O5 is 25.8 kJ/mol.

The interaction of bonding donor orbital, 4, for C1-H4 with the antibonding acceptor orbital, 113, for C2-H7 is 20.7 kJ/mol.

The interaction of bonding donor orbital, 6, for C2-H7 with the antibonding acceptor orbital, 111, for C1-H4 is 20.2 kJ/mol.

The interaction of the second lone pair donor orbital, 12, for O5 with the antibonding acceptor orbital, 108, for C1-C2 is 44.0 kJ/mol.

The interaction of the second lone pair donor orbital, 12, for O5 with the antibonding acceptor orbital, 113, for C2-H7 is 94.4 kJ/mol.

The interaction of the third lone pair donor orbital, 13, for O5 with the second antibonding acceptor orbital, 109, for C1-C2 is 437. kJ/mol.

The interaction of the second bonding donor orbital, 2, for C1-C2 with the lone pair acceptor orbital, 14, for Li6 is 36.7 kJ/mol.

The interaction of bonding donor orbital, 4, for C1-H4 with the lone pair acceptor orbital, 14, for Li6 is 8.61 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-O5 with the lone pair acceptor orbital, 14, for Li6 is 3.38 kJ/mol.

The interaction of bonding donor orbital, 6, for C2-H7 with the lone pair acceptor orbital, 14, for Li6 is 4.76 kJ/mol.

The interaction of lone pair donor orbital, 11, for O5 with the lone pair acceptor orbital, 14, for Li6 is 19.9 kJ/mol.

The interaction of the second lone pair donor orbital, 12, for O5 with the lone pair acceptor orbital, 14, for Li6 is 16.0 kJ/mol.

The interaction of the third lone pair donor orbital, 13, for O5 with the lone pair acceptor orbital, 14, for Li6 is 2.51 kJ/mol.

The interaction of the second antibonding donor orbital, 109, for C1-C2 with the lone pair acceptor orbital, 14, for Li6 is 4.64 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.

17 ----- 1.297

16 ----- 0.585


15 ----- -0.216


14 ----- -1.547


13 -^-v- -4.826

12 -^-v- -5.413


11 -^-v- -8.445

10 -^-v- -8.735


9 -^-v- -9.939

8 -^-v- -10.87


7 -^-v- -13.05


6 -^-v- -17.28


5 -^-v- -24.02


4 -^-v- -51.15


3 -^-v- -265.4


2 -^-v- -267.3


1 -^-v- -504.8

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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 = -160.8214349604 Hartrees

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