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.
The Lewis structure is built for the up and down electrons,
separately. Note that the up and down structures can be very
different.
Hybridization in the Best Lewis Structure
Down Electrons
1. A bonding orbital for C1-C2 with 0.9821 electrons
__has 47.14% C 1 character in a s0.41 p3 hybrid
__has 52.86% C 2 character in a s0.51 p3 hybrid
2. A bonding orbital for C1-C9 with 0.9957 electrons
__has 51.46% C 1 character in a sp2.10 hybrid
__has 48.54% C 9 character in a sp2.30 hybrid
3. A bonding orbital for C1-C13 with 0.9960 electrons
__has 51.33% C 1 character in a sp2.11 hybrid
__has 48.67% C13 character in a sp2.29 hybrid
4. A bonding orbital for C1-H17 with 0.9888 electrons
__has 61.00% C 1 character in a s0.94 p3 hybrid
__has 39.00% H17 character in a s orbital
5. A bonding orbital for C2-C3 with 0.9980 electrons
__has 51.27% C 2 character in a sp1.94 hybrid
__has 48.73% C 3 character in a sp2.33 hybrid
6. A bonding orbital for C2-H7 with 0.9943 electrons
__has 61.21% C 2 character in a sp2.90 hybrid
__has 38.79% H 7 character in a s orbital
7. A bonding orbital for C2-H8 with 0.9936 electrons
__has 61.25% C 2 character in a sp2.83 hybrid
__has 38.75% H 8 character in a s orbital
8. A bonding orbital for C3-H4 with 0.9949 electrons
__has 61.34% C 3 character in a sp2.97 hybrid
__has 38.66% H 4 character in a s orbital
9. A bonding orbital for C3-H5 with 0.9878 electrons
__has 60.82% C 3 character in a s0.77 p3 hybrid
__has 39.18% H 5 character in a s orbital
10. A bonding orbital for C3-H6 with 0.9945 electrons
__has 61.18% C 3 character in a s0.97 p3 hybrid
__has 38.82% H 6 character in a s orbital
11. A bonding orbital for C9-H10 with 0.9881 electrons
__has 60.80% C 9 character in a s0.79 p3 hybrid
__has 39.20% H10 character in a s orbital
12. A bonding orbital for C9-H11 with 0.9939 electrons
__has 61.20% C 9 character in a s0.96 p3 hybrid
__has 38.80% H11 character in a s orbital
13. A bonding orbital for C9-H12 with 0.9947 electrons
__has 61.26% C 9 character in a s0.97 p3 hybrid
__has 38.74% H12 character in a s orbital
14. A bonding orbital for C13-H14 with 0.9879 electrons
__has 60.77% C13 character in a s0.79 p3 hybrid
__has 39.23% H14 character in a s orbital
15. A bonding orbital for C13-H15 with 0.9944 electrons
__has 61.15% C13 character in a s0.96 p3 hybrid
__has 38.85% H15 character in a s orbital
16. A bonding orbital for C13-H16 with 0.9938 electrons
__has 61.33% C13 character in a s0.98 p3 hybrid
__has 38.67% H16 character in a s orbital
-With core pairs on: C 1 C 2 C 3 C 9 C13 -
Up Electrons
1. A bonding orbital for C1-C9 with 0.9926 electrons
__has 50.60% C 1 character in a sp1.85 hybrid
__has 49.40% C 9 character in a sp2.30 hybrid
2. A bonding orbital for C1-C13 with 0.9925 electrons
__has 50.50% C 1 character in a sp1.85 hybrid
__has 49.50% C13 character in a sp2.30 hybrid
3. A bonding orbital for C1-H17 with 0.9772 electrons
__has 61.24% C 1 character in a sp2.38 hybrid
__has 38.76% H17 character in a s orbital
4. A bonding orbital for C2-C3 with 0.9949 electrons
__has 49.99% C 2 character in a sp1.70 hybrid
__has 50.01% C 3 character in a sp2.33 hybrid
5. A bonding orbital for C2-H7 with 0.9840 electrons
__has 60.69% C 2 character in a sp2.19 hybrid
__has 39.31% H 7 character in a s orbital
6. A bonding orbital for C2-H8 with 0.9873 electrons
__has 60.27% C 2 character in a sp2.23 hybrid
__has 39.73% H 8 character in a s orbital
7. A bonding orbital for C3-H4 with 0.9937 electrons
__has 61.64% C 3 character in a s0.98 p3 hybrid
__has 38.36% H 4 character in a s orbital
8. A bonding orbital for C3-H5 with 0.9514 electrons
__has 63.92% C 3 character in a s0.81 p3 hybrid
__has 36.08% H 5 character in a s orbital
9. A bonding orbital for C3-H6 with 0.9900 electrons
__has 61.90% C 3 character in a s0.94 p3 hybrid
__has 38.10% H 6 character in a s orbital
10. A bonding orbital for C9-H10 with 0.9573 electrons
__has 63.65% C 9 character in a s0.84 p3 hybrid
__has 36.35% H10 character in a s orbital
11. A bonding orbital for C9-H11 with 0.9908 electrons
__has 61.61% C 9 character in a s0.94 p3 hybrid
__has 38.39% H11 character in a s orbital
12. A bonding orbital for C9-H12 with 0.9932 electrons
__has 61.60% C 9 character in a s0.95 p3 hybrid
__has 38.40% H12 character in a s orbital
13. A bonding orbital for C13-H14 with 0.9561 electrons
__has 63.82% C13 character in a s0.84 p3 hybrid
__has 36.18% H14 character in a s orbital
14. A bonding orbital for C13-H15 with 0.9912 electrons
__has 61.71% C13 character in a s0.93 p3 hybrid
__has 38.29% H15 character in a s orbital
15. A bonding orbital for C13-H16 with 0.9923 electrons
__has 61.62% C13 character in a s0.95 p3 hybrid
__has 38.38% H16 character in a s orbital
21. A lone pair orbital for C1 with 0.1152 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, 10, for C9-H10 with
the lone pair acceptor orbital, 21, for C1 is 67.0 kJ/mol.
The interaction of bonding donor orbital, 13, for C13-H14 with
the lone pair acceptor orbital, 21, for C1 is 69.1 kJ/mol.
The interaction of bonding donor orbital, 1, for C1-C9 with
the lone pair acceptor orbital, 22, for C2 is 18.8 kJ/mol.
The interaction of bonding donor orbital, 2, for C1-C13 with
the lone pair acceptor orbital, 22, for C2 is 20.8 kJ/mol.
The interaction of bonding donor orbital, 3, for C1-H17 with
the lone pair acceptor orbital, 22, for C2 is 45.8 kJ/mol.
The interaction of lone pair donor orbital, 21, for C1 with
the lone pair acceptor orbital, 22, for C2 is 865. kJ/mol.
The interaction of bonding donor orbital, 4, for C2-C3 with
the lone pair acceptor orbital, 21, for C1 is 19.9 kJ/mol.
The interaction of bonding donor orbital, 5, for C2-H7 with
the lone pair acceptor orbital, 21, for C1 is 42.6 kJ/mol.
The interaction of bonding donor orbital, 6, for C2-H8 with
the lone pair acceptor orbital, 21, for C1 is 31.5 kJ/mol.
The interaction of bonding donor orbital, 8, for C3-H5 with
the lone pair acceptor orbital, 22, for C2 is 77.0 kJ/mol.
Top of page.
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.
Only the spin up electron orbital energies are given.
25 ----- -2.806
24 ----- -3.061
23 ----- -3.735
22 ----- -5.762
21 -^--- -12.10
20 -^-v- -13.79
19 -^-v- -13.83
18 -^-v- -14.00
17 -^-v- -14.36
16 -^-v- -14.70
15 -^-v- -15.07
14 -^-v- -15.74
13 -^-v- -16.19
12 -^-v- -16.48
11 -^-v- -17.11
10 -^-v- -19.30
9 -^-v- -20.61
8 -^-v- -22.30
7 -^-v- -24.09
6 -^-v- -25.62
5 -^-v- -271.3 4 -^-v- -271.3
3 -^-v- -271.4
2 -^-v- -273.2
1 -^-v- -273.4
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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 = -197.4658767219 Hartrees
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