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 1.9365 electrons
__has 74.42% C 1 character in a sp0.09 hybrid
__has 25.58% C 2 character in a sp0.76 d0.05 hybrid
2. A antibonding orbital for C1-C2 with 1.6261 electrons
__has 56.74% C 1 character in a sp1.52 d0.08 hybrid
__has 43.26% C 2 character in a sp1.28 d0.25 hybrid
3. A bonding orbital for C1-C3 with 1.7355 electrons
__has 75.07% C 1 character in a sp0.73 hybrid
__has 24.93% C 3 character in a p3 hybrid
4. A antibonding orbital for C1-C3 with 1.6225 electrons
__has 22.74% C 1 character in a sp2.16 d0.21 hybrid
__has 77.26% C 3 character in a sp1.87 hybrid
5. A antibonding orbital for C2-C3 with 1.5247 electrons
__has 21.04% C 2 character in a s0.79 p3 d0.20 hybrid
__has 78.96% C 3 character in a sp0.56 d0.10 hybrid
9. A lone pair orbital for C2 with 1.9148 electrons
__made from a s orbital
10. A lone pair orbital for C3 with 0.4229 electrons
__made from a sp2.27 d0.14 hybrid
69. A bonding orbital for C1-C2 with 0.1710 electrons
__has 43.26% C 1 character in a sp1.52 d0.08 hybrid
__has 56.74% C 2 character in a sp1.28 d0.25 hybrid
-With core pairs on: C 1 C 2 C 3 -
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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, 1, for C1-C2 with
the antibonding acceptor orbital, 5, for C2-C3 is 1823 kJ/mol.
The interaction of bonding donor orbital, 1, for C1-C2 with
the lone pair acceptor orbital, 10, for C3 is 5982 kJ/mol.
The interaction of bonding donor orbital, 1, for C1-C2 with
the antibonding acceptor orbital, 68, for C1-C2 is 422. kJ/mol.
The interaction of bonding donor orbital, 1, for C1-C2 with
the antibonding acceptor orbital, 70, for C1-C3 is 919. kJ/mol.
The interaction of bonding donor orbital, 1, for C1-C2 with
the bonding acceptor orbital, 72, for C2-C3 is 2537 kJ/mol.
The interaction of the second antibonding donor orbital, 2, for C1-C2 with
the second antibonding acceptor orbital, 4, for C1-C3 is 1713 kJ/mol.
The interaction of the second antibonding donor orbital, 2, for C1-C2 with
the antibonding acceptor orbital, 5, for C2-C3 is 2646 kJ/mol.
The interaction of the second antibonding donor orbital, 2, for C1-C2 with
the lone pair acceptor orbital, 10, for C3 is 1344 kJ/mol.
The interaction of the second antibonding donor orbital, 2, for C1-C2 with
the antibonding acceptor orbital, 68, for C1-C2 is 443. kJ/mol.
The interaction of the second antibonding donor orbital, 2, for C1-C2 with
the second bonding acceptor orbital, 69, for C1-C2 is 1914 kJ/mol.
The interaction of the second antibonding donor orbital, 2, for C1-C2 with
the antibonding acceptor orbital, 70, for C1-C3 is 1436 kJ/mol.
The interaction of the second antibonding donor orbital, 2, for C1-C2 with
the bonding acceptor orbital, 72, for C2-C3 is 8951 kJ/mol.
The interaction of bonding donor orbital, 3, for C1-C3 with
the second antibonding acceptor orbital, 2, for C1-C2 is 1450 kJ/mol.
The interaction of bonding donor orbital, 3, for C1-C3 with
the second antibonding acceptor orbital, 4, for C1-C3 is 1939 kJ/mol.
The interaction of bonding donor orbital, 3, for C1-C3 with
the antibonding acceptor orbital, 5, for C2-C3 is 78.6 kJ/mol.
The interaction of bonding donor orbital, 3, for C1-C3 with
the lone pair acceptor orbital, 10, for C3 is 6140 kJ/mol.
The interaction of bonding donor orbital, 3, for C1-C3 with
the antibonding acceptor orbital, 68, for C1-C2 is 1383 kJ/mol.
The interaction of bonding donor orbital, 3, for C1-C3 with
the second bonding acceptor orbital, 69, for C1-C2 is 2288 kJ/mol.
The interaction of bonding donor orbital, 3, for C1-C3 with
the antibonding acceptor orbital, 70, for C1-C3 is 747. kJ/mol.
The interaction of bonding donor orbital, 3, for C1-C3 with
the second bonding acceptor orbital, 71, for C1-C3 is 4530 kJ/mol.
The interaction of bonding donor orbital, 3, for C1-C3 with
the bonding acceptor orbital, 72, for C2-C3 is 3105 kJ/mol.
The interaction of the second antibonding donor orbital, 4, for C1-C3 with
the antibonding acceptor orbital, 5, for C2-C3 is 3543 kJ/mol.
The interaction of the second antibonding donor orbital, 4, for C1-C3 with
the lone pair acceptor orbital, 10, for C3 is 1815 kJ/mol.
The interaction of the second antibonding donor orbital, 4, for C1-C3 with
the antibonding acceptor orbital, 68, for C1-C2 is 406. kJ/mol.
The interaction of the second antibonding donor orbital, 4, for C1-C3 with
the antibonding acceptor orbital, 70, for C1-C3 is 1057 kJ/mol.
The interaction of the second antibonding donor orbital, 4, for C1-C3 with
the second bonding acceptor orbital, 71, for C1-C3 is 1392 kJ/mol.
The interaction of the second antibonding donor orbital, 4, for C1-C3 with
the bonding acceptor orbital, 72, for C2-C3 is 5653 kJ/mol.
The interaction of antibonding donor orbital, 5, for C2-C3 with
the lone pair acceptor orbital, 10, for C3 is 4511 kJ/mol.
The interaction of antibonding donor orbital, 5, for C2-C3 with
the antibonding acceptor orbital, 68, for C1-C2 is 3280 kJ/mol.
The interaction of antibonding donor orbital, 5, for C2-C3 with
the antibonding acceptor orbital, 70, for C1-C3 is 3361 kJ/mol.
The interaction of antibonding donor orbital, 5, for C2-C3 with
the second bonding acceptor orbital, 71, for C1-C3 is 2792 kJ/mol.
The interaction of antibonding donor orbital, 5, for C2-C3 with
the bonding acceptor orbital, 72, for C2-C3 is 7287 kJ/mol.
The interaction of lone pair donor orbital, 9, for C2 with
the second antibonding acceptor orbital, 2, for C1-C2 is 144. kJ/mol.
The interaction of lone pair donor orbital, 9, for C2 with
the second antibonding acceptor orbital, 4, for C1-C3 is 3273 kJ/mol.
The interaction of lone pair donor orbital, 9, for C2 with
the antibonding acceptor orbital, 5, for C2-C3 is 1565 kJ/mol.
The interaction of lone pair donor orbital, 9, for C2 with
the lone pair acceptor orbital, 10, for C3 is 9277 kJ/mol.
The interaction of lone pair donor orbital, 9, for C2 with
the second bonding acceptor orbital, 69, for C1-C2 is 2721 kJ/mol.
The interaction of lone pair donor orbital, 9, for C2 with
the antibonding acceptor orbital, 70, for C1-C3 is 1180 kJ/mol.
The interaction of lone pair donor orbital, 9, for C2 with
the second bonding acceptor orbital, 71, for C1-C3 is 1581 kJ/mol.
The interaction of lone pair donor orbital, 9, for C2 with
the bonding acceptor orbital, 72, for C2-C3 is 3166 kJ/mol.
The interaction of lone pair donor orbital, 10, for C3 with
the antibonding acceptor orbital, 70, for C1-C3 is 1455 kJ/mol.
The interaction of lone pair donor orbital, 10, for C3 with
the second bonding acceptor orbital, 71, for C1-C3 is 2194 kJ/mol.
The interaction of lone pair donor orbital, 10, for C3 with
the bonding acceptor orbital, 72, for C2-C3 is 1252 kJ/mol.
The interaction of the second bonding donor orbital, 69, for C1-C2 with
the second antibonding acceptor orbital, 4, for C1-C3 is 9567 kJ/mol.
The interaction of the second bonding donor orbital, 69, for C1-C2 with
the antibonding acceptor orbital, 5, for C2-C3 is 6763 kJ/mol.
The interaction of the second bonding donor orbital, 69, for C1-C2 with
the lone pair acceptor orbital, 10, for C3 is 9418 kJ/mol.
The interaction of the second bonding donor orbital, 69, for C1-C2 with
the antibonding acceptor orbital, 70, for C1-C3 is 8029 kJ/mol.
The interaction of the second bonding donor orbital, 69, for C1-C2 with
the second bonding acceptor orbital, 71, for C1-C3 is 1219 kJ/mol.
The interaction of the second bonding donor orbital, 69, for C1-C2 with
the bonding acceptor orbital, 72, for C2-C3 is 2774 kJ/mol.
The interaction of the second bonding donor orbital, 71, for C1-C3 with
the antibonding acceptor orbital, 70, for C1-C3 is 6092 kJ/mol.
The interaction of bonding donor orbital, 72, for C2-C3 with
the antibonding acceptor orbital, 70, for C1-C3 is 867. kJ/mol.
The interaction of bonding donor orbital, 72, for C2-C3 with
the second bonding acceptor orbital, 71, for C1-C3 is 1051 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.
13 ----- 0.170 12 ----- 0.169
11 ----- -5.777 10 ----- -5.778
9 -^-v- -7.986
8 -^-v- -8.799
7 -^-v- -9.782 6 -^-v- -9.782
5 -^-v- -18.22
4 -^-v- -21.05
3 -^-v- -267.8
2 -^-v- -270.0 1 -^-v- -270.0
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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 = -114.0745290781 Hartrees
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