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 1.9825 electrons
__has 49.14% C 1 character in a sp1.97 hybrid
__has 50.86% C 2 character in a sp2.40 hybrid
2. A bonding orbital for C1-C9 with 1.9850 electrons
__has 48.95% C 1 character in a sp2.01 hybrid
__has 51.05% C 9 character in a sp2.21 hybrid
3. A bonding orbital for C1-C13 with 1.9850 electrons
__has 48.92% C 1 character in a sp2.01 hybrid
__has 51.08% C13 character in a sp2.21 hybrid
4. A bonding orbital for C2-C3 with 1.9244 electrons
__has 54.94% C 2 character in a s0.96 p3 hybrid
__has 45.06% C 3 character in a sp2.96 hybrid
5. A bonding orbital for C2-H7 with 1.9647 electrons
__has 62.14% C 2 character in a s0.88 p3 hybrid
__has 37.86% H 7 character in a s orbital
6. A bonding orbital for C2-H8 with 1.9764 electrons
__has 61.80% C 2 character in a s0.93 p3 hybrid
__has 38.20% H 8 character in a s orbital
7. A bonding orbital for C3-H4 with 1.9933 electrons
__has 60.31% C 3 character in a sp2.94 hybrid
__has 39.69% H 4 character in a s orbital
8. A bonding orbital for C3-H5 with 1.9931 electrons
__has 60.42% C 3 character in a sp2.93 hybrid
__has 39.58% H 5 character in a s orbital
9. A bonding orbital for C3-H6 with 1.9825 electrons
__has 61.78% C 3 character in a s0.95 p3 hybrid
__has 38.22% H 6 character in a s orbital
10. A bonding orbital for C9-H10 with 1.9881 electrons
__has 62.19% C 9 character in a sp2.91 hybrid
__has 37.81% H10 character in a s orbital
11. A bonding orbital for C9-H11 with 1.9471 electrons
__has 63.08% C 9 character in a s0.84 p3 hybrid
__has 36.92% H11 character in a s orbital
12. A bonding orbital for C9-H12 with 1.9410 electrons
__has 63.22% C 9 character in a s0.82 p3 hybrid
__has 36.78% H12 character in a s orbital
13. A bonding orbital for C13-H14 with 1.9262 electrons
__has 63.24% C13 character in a s0.77 p3 hybrid
__has 36.76% H14 character in a s orbital
14. A bonding orbital for C13-H15 with 1.9863 electrons
__has 62.28% C13 character in a sp2.94 hybrid
__has 37.72% H15 character in a s orbital
15. A bonding orbital for C13-H16 with 1.9628 electrons
__has 62.79% C13 character in a s0.90 p3 hybrid
__has 37.21% H16 character in a s orbital
21. A lone pair orbital for C1 with 0.2954 electrons
__made from a p3 hybrid
-With core pairs on: C 1 C 2 C 3 C 9 C13 -
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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, 4, for C2-C3 with
the lone pair acceptor orbital, 21, for C1 is 105. kJ/mol.
The interaction of bonding donor orbital, 5, for C2-H7 with
the lone pair acceptor orbital, 21, for C1 is 23.8 kJ/mol.
The interaction of bonding donor orbital, 5, for C2-H7 with
the antibonding acceptor orbital, 174, for C1-C13 is 24.9 kJ/mol.
The interaction of bonding donor orbital, 6, for C2-H8 with
the antibonding acceptor orbital, 173, for C1-C9 is 28.9 kJ/mol.
The interaction of bonding donor orbital, 10, for C9-H10 with
the antibonding acceptor orbital, 174, for C1-C13 is 30.0 kJ/mol.
The interaction of bonding donor orbital, 11, for C9-H11 with
the lone pair acceptor orbital, 21, for C1 is 64.0 kJ/mol.
The interaction of bonding donor orbital, 12, for C9-H12 with
the lone pair acceptor orbital, 21, for C1 is 77.1 kJ/mol.
The interaction of bonding donor orbital, 13, for C13-H14 with
the lone pair acceptor orbital, 21, for C1 is 109. kJ/mol.
The interaction of bonding donor orbital, 14, for C13-H15 with
the antibonding acceptor orbital, 172, for C1-C2 is 26.6 kJ/mol.
The interaction of bonding donor orbital, 15, for C13-H16 with
the lone pair acceptor orbital, 21, for C1 is 35.4 kJ/mol.
The interaction of bonding donor orbital, 15, for C13-H16 with
the antibonding acceptor orbital, 173, for C1-C9 is 23.3 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 ----- -2.658
23 ----- -3.028
22 ----- -3.711
21 ----- -9.380
20 -^-v- -13.45
19 -^-v- -13.66
18 -^-v- -14.25
17 -^-v- -14.56
16 -^-v- -14.89
15 -^-v- -14.93
14 -^-v- -15.20
13 -^-v- -16.51
12 -^-v- -17.04
11 -^-v- -17.11
10 -^-v- -18.65
9 -^-v- -20.86
8 -^-v- -23.01
7 -^-v- -23.68
6 -^-v- -26.54
5 -^-v- -271.3
4 -^-v- -271.8 3 -^-v- -271.9
2 -^-v- -272.0
1 -^-v- -274.6
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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 = -196.9184380995 Hartrees
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