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.
Hybridization in the Best Lewis Structure
1. A bonding orbital for H1-C2 with 1.9846 electrons
__has 39.65% H 1 character in a s orbital
__has 60.35% C 2 character in a sp2.25 hybrid
2. A bonding orbital for C2-C3 with 1.9939 electrons
__has 48.70% C 2 character in a sp1.53 hybrid
__has 51.30% C 3 character in a sp1.36 hybrid
3. A bonding orbital for C2-C3 with 1.9790 electrons
__has 50.00% C 2 character in a p-pi orbital ( 99.82% p 0.18% d)
__has 50.00% C 3 character in a p-pi orbital ( 99.86% p 0.14% d)
4. A bonding orbital for C2-H9 with 1.9769 electrons
__has 59.68% C 2 character in a sp2.34 hybrid
__has 40.32% H 9 character in a s orbital
5. A bonding orbital for C3-C4 with 1.9903 electrons
__has 50.96% C 3 character in a sp1.79 hybrid
__has 49.04% C 4 character in a sp2.38 hybrid
6. A bonding orbital for C3-Cl8 with 1.9864 electrons
__has 43.47% C 3 character in a s0.85 p3 hybrid
__has 56.53% Cl 8 character in a s0.63 p3 hybrid
7. A bonding orbital for C4-H5 with 1.9834 electrons
__has 59.91% C 4 character in a s0.94 p3 hybrid
__has 40.09% H 5 character in a s orbital
8. A bonding orbital for C4-H6 with 1.9827 electrons
__has 60.35% C 4 character in a s0.91 p3 hybrid
__has 39.65% H 6 character in a s orbital
9. A bonding orbital for C4-H7 with 1.9824 electrons
__has 60.34% C 4 character in a s0.91 p3 hybrid
__has 39.66% H 7 character in a s orbital
18. A lone pair orbital for Cl8 with 1.9910 electrons
__made from a sp0.20 hybrid
19. A lone pair orbital for Cl8 with 1.9775 electrons
__made from a p3 hybrid
20. A lone pair orbital for Cl8 with 1.9533 electrons
__made from a p-pi orbital ( 99.98% p)
-With core pairs on: C 2 C 3 C 4 Cl 8 Cl 8 Cl 8 Cl 8 Cl 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, 1, for H1-C2 with
the antibonding acceptor orbital, 129, for C3-C4 is 36.4 kJ/mol.
The interaction of bonding donor orbital, 4, for C2-H9 with
the antibonding acceptor orbital, 130, for C3-Cl8 is 49.2 kJ/mol.
The interaction of bonding donor orbital, 7, for C4-H5 with
the antibonding acceptor orbital, 130, for C3-Cl8 is 35.1 kJ/mol.
The interaction of bonding donor orbital, 8, for C4-H6 with
the second antibonding acceptor orbital, 127, for C2-C3 is 21.8 kJ/mol.
The interaction of bonding donor orbital, 9, for C4-H7 with
the second antibonding acceptor orbital, 127, for C2-C3 is 22.6 kJ/mol.
The interaction of the second lone pair donor orbital, 19, for Cl8 with
the antibonding acceptor orbital, 126, for C2-C3 is 20.5 kJ/mol.
The interaction of the second lone pair donor orbital, 19, for Cl8 with
the antibonding acceptor orbital, 129, for C3-C4 is 22.1 kJ/mol.
The interaction of the third lone pair donor orbital, 20, for Cl8 with
the second antibonding acceptor orbital, 127, for C2-C3 is 76.7 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.
24 ----- 1.979
23 ----- 1.807
22 ----- -0.379
21 ----- -1.285
20 -^-v- -6.314
19 -^-v- -7.448
18 -^-v- -8.357
17 -^-v- -9.213
16 -^-v- -9.589
15 -^-v- -10.71
14 -^-v- -11.18
13 -^-v- -11.80
12 -^-v- -13.44
11 -^-v- -17.36
10 -^-v- -18.87
9 -^-v- -21.69
8 -^-v- -190.1
7 -^-v- -190.1
6 -^-v- -190.5
5 -^-v- -248.5
4 -^-v- -266.4
3 -^-v- -266.6
2 -^-v- -268.3
1 -^-v- -2729.
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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 = -577.5885652334 Hartrees
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