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 C1-C2 with 0.9909 electrons
__has 49.41% C 1 character in a sp2.27 hybrid
__has 50.59% C 2 character in a sp2.00 hybrid
2. A bonding orbital for C1-C6 with 0.9905 electrons
__has 49.58% C 1 character in a sp2.27 hybrid
__has 50.42% C 6 character in a sp2.00 hybrid
3. A bonding orbital for C1-C10 with 0.9909 electrons
__has 49.43% C 1 character in a sp2.26 hybrid
__has 50.57% C10 character in a sp2.00 hybrid
4. A bonding orbital for C1-C14 with 0.9670 electrons
__has 42.36% C 1 character in a s0.28 p3 hybrid
__has 57.64% C14 character in a s0.50 p3 hybrid
5. A bonding orbital for C2-H3 with 0.9919 electrons
__has 60.53% C 2 character in a s0.91 p3 hybrid
__has 39.47% H 3 character in a s orbital
6. A bonding orbital for C2-H4 with 0.9848 electrons
__has 60.13% C 2 character in a s0.75 p3 hybrid
__has 39.87% H 4 character in a s orbital
7. A bonding orbital for C2-H5 with 0.9919 electrons
__has 60.64% C 2 character in a s0.92 p3 hybrid
__has 39.36% H 5 character in a s orbital
8. A bonding orbital for C6-H7 with 0.9919 electrons
__has 60.54% C 6 character in a s0.91 p3 hybrid
__has 39.46% H 7 character in a s orbital
9. A bonding orbital for C6-H8 with 0.9919 electrons
__has 60.57% C 6 character in a s0.91 p3 hybrid
__has 39.43% H 8 character in a s orbital
10. A bonding orbital for C6-H9 with 0.9847 electrons
__has 60.25% C 6 character in a s0.76 p3 hybrid
__has 39.75% H 9 character in a s orbital
11. A bonding orbital for C10-H11 with 0.9847 electrons
__has 60.13% C10 character in a s0.75 p3 hybrid
__has 39.87% H11 character in a s orbital
12. A bonding orbital for C10-H12 with 0.9920 electrons
__has 60.55% C10 character in a s0.91 p3 hybrid
__has 39.45% H12 character in a s orbital
13. A bonding orbital for C10-H13 with 0.9919 electrons
__has 60.64% C10 character in a s0.92 p3 hybrid
__has 39.36% H13 character in a s orbital
14. A bonding orbital for C14-C15 with 0.9972 electrons
__has 50.98% C14 character in a sp1.89 hybrid
__has 49.02% C15 character in a sp2.24 hybrid
15. A bonding orbital for C14-H19 with 0.9928 electrons
__has 60.32% C14 character in a sp2.88 hybrid
__has 39.68% H19 character in a s orbital
16. A bonding orbital for C14-H20 with 0.9928 electrons
__has 60.33% C14 character in a sp2.88 hybrid
__has 39.67% H20 character in a s orbital
17. A bonding orbital for C15-H16 with 0.9868 electrons
__has 60.12% C15 character in a s0.76 p3 hybrid
__has 39.88% H16 character in a s orbital
18. A bonding orbital for C15-H17 with 0.9941 electrons
__has 60.48% C15 character in a s0.97 p3 hybrid
__has 39.52% H17 character in a s orbital
19. A bonding orbital for C15-H18 with 0.9941 electrons
__has 60.49% C15 character in a s0.97 p3 hybrid
__has 39.51% H18 character in a s orbital
-With core pairs on: C 1 C 2 C 6 C10 C14 C15 -
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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, 366, for C6-H8 is 5.27 kJ/mol.
The interaction of bonding donor orbital, 1, for C1-C2 with
the antibonding acceptor orbital, 369, for C10-H12 is 5.23 kJ/mol.
The interaction of bonding donor orbital, 2, for C1-C6 with
the antibonding acceptor orbital, 364, for C2-H5 is 5.27 kJ/mol.
The interaction of bonding donor orbital, 2, for C1-C6 with
the antibonding acceptor orbital, 370, for C10-H13 is 5.23 kJ/mol.
The interaction of bonding donor orbital, 3, for C1-C10 with
the antibonding acceptor orbital, 362, for C2-H3 is 5.18 kJ/mol.
The interaction of bonding donor orbital, 3, for C1-C10 with
the antibonding acceptor orbital, 365, for C6-H7 is 5.23 kJ/mol.
The interaction of bonding donor orbital, 4, for C1-C14 with
the antibonding acceptor orbital, 362, for C2-H3 is 1.12 kJ/mol.
The interaction of bonding donor orbital, 4, for C1-C14 with
the antibonding acceptor orbital, 363, for C2-H4 is 12.4 kJ/mol.
The interaction of bonding donor orbital, 4, for C1-C14 with
the antibonding acceptor orbital, 367, for C6-H9 is 11.5 kJ/mol.
The interaction of bonding donor orbital, 4, for C1-C14 with
the antibonding acceptor orbital, 368, for C10-H11 is 12.3 kJ/mol.
The interaction of bonding donor orbital, 4, for C1-C14 with
the antibonding acceptor orbital, 369, for C10-H12 is 1.08 kJ/mol.
The interaction of bonding donor orbital, 4, for C1-C14 with
the antibonding acceptor orbital, 374, for C15-H16 is 8.36 kJ/mol.
The interaction of bonding donor orbital, 5, for C2-H3 with
the antibonding acceptor orbital, 360, for C1-C10 is 16.0 kJ/mol.
The interaction of bonding donor orbital, 5, for C2-H3 with
the antibonding acceptor orbital, 361, for C1-C14 is 1.08 kJ/mol.
The interaction of bonding donor orbital, 6, for C2-H4 with
the antibonding acceptor orbital, 361, for C1-C14 is 24.5 kJ/mol.
The interaction of bonding donor orbital, 7, for C2-H5 with
the antibonding acceptor orbital, 359, for C1-C6 is 15.8 kJ/mol.
The interaction of bonding donor orbital, 8, for C6-H7 with
the antibonding acceptor orbital, 360, for C1-C10 is 15.9 kJ/mol.
The interaction of bonding donor orbital, 9, for C6-H8 with
the antibonding acceptor orbital, 358, for C1-C2 is 15.8 kJ/mol.
The interaction of bonding donor orbital, 10, for C6-H9 with
the antibonding acceptor orbital, 361, for C1-C14 is 24.4 kJ/mol.
The interaction of bonding donor orbital, 11, for C10-H11 with
the antibonding acceptor orbital, 361, for C1-C14 is 24.7 kJ/mol.
The interaction of bonding donor orbital, 12, for C10-H12 with
the antibonding acceptor orbital, 358, for C1-C2 is 16.0 kJ/mol.
The interaction of bonding donor orbital, 12, for C10-H12 with
the antibonding acceptor orbital, 361, for C1-C14 is 1.04 kJ/mol.
The interaction of bonding donor orbital, 13, for C10-H13 with
the antibonding acceptor orbital, 359, for C1-C6 is 15.8 kJ/mol.
The interaction of bonding donor orbital, 13, for C10-H13 with
the antibonding acceptor orbital, 361, for C1-C14 is 1.04 kJ/mol.
The interaction of bonding donor orbital, 15, for C14-H19 with
the antibonding acceptor orbital, 360, for C1-C10 is 2.46 kJ/mol.
The interaction of bonding donor orbital, 15, for C14-H19 with
the antibonding acceptor orbital, 376, for C15-H18 is 8.40 kJ/mol.
The interaction of bonding donor orbital, 16, for C14-H20 with
the antibonding acceptor orbital, 358, for C1-C2 is 2.42 kJ/mol.
The interaction of bonding donor orbital, 16, for C14-H20 with
the antibonding acceptor orbital, 375, for C15-H17 is 8.40 kJ/mol.
The interaction of bonding donor orbital, 17, for C15-H16 with
the antibonding acceptor orbital, 361, for C1-C14 is 18.8 kJ/mol.
The interaction of bonding donor orbital, 18, for C15-H17 with
the antibonding acceptor orbital, 373, for C14-H20 is 10.0 kJ/mol.
The interaction of bonding donor orbital, 19, for C15-H18 with
the antibonding acceptor orbital, 372, for C14-H19 is 10.0 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.
Only the spin up electron orbital energies are given.
29 ----- -2.627
28 ----- -2.925
27 ----- -3.615
26 ----- -6.234
25 -^--- -11.45
24 -^-v- -13.56
23 -^-v- -13.58
22 -^-v- -13.61
21 -^-v- -13.82
20 -^-v- -14.09
19 -^-v- -14.17
18 -^-v- -14.56
17 -^-v- -15.13
16 -^-v- -15.85
15 -^-v- -16.03
14 -^-v- -16.48
13 -^-v- -16.63
12 -^-v- -18.15
11 -^-v- -20.23
10 -^-v- -22.04
9 -^-v- -22.07
8 -^-v- -23.96
7 -^-v- -25.67
6 -^-v- -271.0
5 -^-v- -271.1 4 -^-v- -271.1
3 -^-v- -271.2
2 -^-v- -272.9
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 = -236.8007139879 Hartrees
*The calculation of the best Lewis Structure (NBO analysis)
was done without diffuse functions to save time.
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