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-O2 with 1.9977 electrons
__has 36.11% C 1 character in a sp1.74 hybrid
__has 63.89% O 2 character in a sp1.72 hybrid
2. A bonding orbital for C1-O2 with 1.9936 electrons
__has 21.11% C 1 character in a p-pi orbital ( 99.27% p 0.73% d)
__has 78.89% O 2 character in a p-pi orbital ( 99.87% p 0.13% d)
3. A bonding orbital for C1-C3 with 1.9906 electrons
__has 43.00% C 1 character in a sp2.45 hybrid
__has 57.00% C 3 character in a sp2.34 hybrid
4. A bonding orbital for C1-O7 with 1.9935 electrons
__has 36.22% C 1 character in a sp1.87 hybrid
__has 63.78% O 7 character in a sp1.88 hybrid
5. A bonding orbital for C3-Cl4 with 1.9926 electrons
__has 38.14% C 3 character in a s0.67 p3 hybrid
__has 61.86% Cl 4 character in a s0.56 p3 hybrid
6. A bonding orbital for C3-H5 with 1.9873 electrons
__has 59.74% C 3 character in a sp2.82 hybrid
__has 40.26% H 5 character in a s orbital
7. A bonding orbital for C3-H6 with 1.9872 electrons
__has 59.73% C 3 character in a sp2.83 hybrid
__has 40.27% H 6 character in a s orbital
17. A lone pair orbital for O2 with 1.9773 electrons
__made from a sp0.57 hybrid
18. A lone pair orbital for O2 with 1.9011 electrons
__made from a p3 hybrid
19. A lone pair orbital for Cl4 with 1.9984 electrons
__made from a sp0.19 hybrid
20. A lone pair orbital for Cl4 with 1.9886 electrons
__made from a p-pi orbital ( 99.99% p)
21. A lone pair orbital for Cl4 with 1.9837 electrons
__made from a p3 hybrid
22. A lone pair orbital for O7 with 1.9784 electrons
__made from a sp0.52 hybrid
23. A lone pair orbital for O7 with 1.8978 electrons
__made from a p3 hybrid
24. A lone pair orbital for O7 with 1.6926 electrons
__made from a p3 hybrid
134. A antibonding orbital for C1-O2 with 0.3069 electrons
__has 78.89% C 1 character in a p-pi orbital ( 99.27% p 0.73% d)
__has 21.11% O 2 character in a p-pi orbital ( 99.87% p 0.13% d)
135. A antibonding orbital for C1-C3 with 0.1057 electrons
__has 57.00% C 1 character in a sp2.45 hybrid
__has 43.00% C 3 character in a sp2.34 hybrid
-With core pairs on: C 1 O 2 C 3 Cl 4 Cl 4 Cl 4 Cl 4 Cl 4 O 7 -
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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 lone pair donor orbital, 17, for O2 with
the antibonding acceptor orbital, 136, for C1-O7 is 24.0 kJ/mol.
The interaction of the second lone pair donor orbital, 18, for O2 with
the antibonding acceptor orbital, 135, for C1-C3 is 134. kJ/mol.
The interaction of the second lone pair donor orbital, 18, for O2 with
the antibonding acceptor orbital, 136, for C1-O7 is 104. kJ/mol.
The interaction of the third lone pair donor orbital, 21, for Cl4 with
the antibonding acceptor orbital, 135, for C1-C3 is 23.4 kJ/mol.
The interaction of lone pair donor orbital, 22, for O7 with
the antibonding acceptor orbital, 133, for C1-O2 is 21.5 kJ/mol.
The interaction of the second lone pair donor orbital, 23, for O7 with
the antibonding acceptor orbital, 133, for C1-O2 is 93.3 kJ/mol.
The interaction of the second lone pair donor orbital, 23, for O7 with
the antibonding acceptor orbital, 135, for C1-C3 is 94.6 kJ/mol.
The interaction of the second lone pair donor orbital, 23, for O7 with
the antibonding acceptor orbital, 137, for C3-Cl4 is 25.4 kJ/mol.
The interaction of the third lone pair donor orbital, 24, for O7 with
the second antibonding acceptor orbital, 134, for C1-O2 is 626. 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.
28 ----- 7.115
27 ----- 6.098
26 ----- 4.903
25 ----- 3.497
24 -^-v- -0.531
23 -^-v- -0.772
22 -^-v- -1.172
21 -^-v- -2.812
20 -^-v- -2.951
19 -^-v- -4.260
18 -^-v- -4.623
17 -^-v- -5.595
16 -^-v- -5.838
15 -^-v- -6.811
14 -^-v- -7.661
13 -^-v- -12.35
12 -^-v- -16.19
11 -^-v- -18.32
10 -^-v- -20.42
9 -^-v- -185.4
8 -^-v- -185.4
7 -^-v- -185.7
6 -^-v- -243.8
5 -^-v- -263.3
4 -^-v- -263.8
3 -^-v- -500.0
2 -^-v- -500.1
1 -^-v- -2724.
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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 = -688.2724270871 Hartrees
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