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 O1-C2 with 0.9955 electrons
__has 75.97% O 1 character in a sp1.72 hybrid
__has 24.03% C 2 character in a s0.61 p3 hybrid
2. A bonding orbital for O1-C15 with 0.9964 electrons
__has 73.44% O 1 character in a sp2.43 hybrid
__has 26.56% C15 character in a s0.81 p3 hybrid
3. A bonding orbital for C2-C3 with 0.9946 electrons
__has 51.27% C 2 character in a sp2.16 hybrid
__has 48.73% C 3 character in a sp2.27 hybrid
4. A bonding orbital for C2-C7 with 0.9897 electrons
__has 50.65% C 2 character in a s0.93 p3 hybrid
__has 49.35% C 7 character in a sp2.69 hybrid
5. A bonding orbital for C2-C11 with 0.9902 electrons
__has 51.70% C 2 character in a sp2.62 hybrid
__has 48.30% C11 character in a sp2.44 hybrid
6. A bonding orbital for C3-H4 with 0.9937 electrons
__has 60.08% C 3 character in a s0.92 p3 hybrid
__has 39.92% H 4 character in a s orbital
7. A bonding orbital for C3-H5 with 0.9924 electrons
__has 60.10% C 3 character in a s0.88 p3 hybrid
__has 39.90% H 5 character in a s orbital
8. A bonding orbital for C3-H6 with 0.9877 electrons
__has 61.57% C 3 character in a s0.91 p3 hybrid
__has 38.43% H 6 character in a s orbital
9. A bonding orbital for C7-H8 with 0.9953 electrons
__has 59.89% C 7 character in a s0.96 p3 hybrid
__has 40.11% H 8 character in a s orbital
10. A bonding orbital for C7-H9 with 0.9954 electrons
__has 60.68% C 7 character in a sp2.96 hybrid
__has 39.32% H 9 character in a s orbital
11. A bonding orbital for C7-H10 with 0.9928 electrons
__has 60.44% C 7 character in a s0.92 p3 hybrid
__has 39.56% H10 character in a s orbital
12. A bonding orbital for C11-H12 with 0.9911 electrons
__has 60.65% C11 character in a s0.93 p3 hybrid
__has 39.35% H12 character in a s orbital
13. A bonding orbital for C11-H13 with 0.9941 electrons
__has 59.91% C11 character in a s0.89 p3 hybrid
__has 40.09% H13 character in a s orbital
14. A bonding orbital for C11-H14 with 0.9941 electrons
__has 60.56% C11 character in a s0.96 p3 hybrid
__has 39.44% H14 character in a s orbital
15. A bonding orbital for C15-H16 with 0.9976 electrons
__has 60.04% C15 character in a sp2.59 hybrid
__has 39.96% H16 character in a s orbital
16. A bonding orbital for C15-H17 with 0.9977 electrons
__has 59.13% C15 character in a s0.97 p3 hybrid
__has 40.87% H17 character in a s orbital
17. A bonding orbital for C15-H18 with 0.9960 electrons
__has 60.63% C15 character in a sp2.75 hybrid
__has 39.37% H18 character in a s orbital
24. A lone pair orbital for O1 with 0.9893 electrons
__made from a sp1.91 hybrid
25. A lone pair orbital for O1 with 0.9859 electrons
__made from a p3 hybrid
-With core pairs on: O 1 C 2 C 3 C 7 C11 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 O1-C2 with
the antibonding acceptor orbital, 339, for C3-H6 is 1.38 kJ/mol.
The interaction of bonding donor orbital, 1, for O1-C2 with
the antibonding acceptor orbital, 342, for C7-H10 is 1.79 kJ/mol.
The interaction of bonding donor orbital, 1, for O1-C2 with
the antibonding acceptor orbital, 343, for C11-H12 is 1.84 kJ/mol.
The interaction of bonding donor orbital, 1, for O1-C2 with
the antibonding acceptor orbital, 346, for C15-H16 is 1.08 kJ/mol.
The interaction of bonding donor orbital, 2, for O1-C15 with
the antibonding acceptor orbital, 335, for C2-C7 is 1.04 kJ/mol.
The interaction of bonding donor orbital, 2, for O1-C15 with
the antibonding acceptor orbital, 336, for C2-C11 is 3.30 kJ/mol.
The interaction of bonding donor orbital, 3, for C2-C3 with
the antibonding acceptor orbital, 336, for C2-C11 is 1.21 kJ/mol.
The interaction of bonding donor orbital, 3, for C2-C3 with
the antibonding acceptor orbital, 341, for C7-H9 is 2.42 kJ/mol.
The interaction of bonding donor orbital, 3, for C2-C3 with
the antibonding acceptor orbital, 345, for C11-H14 is 2.88 kJ/mol.
The interaction of bonding donor orbital, 4, for C2-C7 with
the antibonding acceptor orbital, 332, for O1-C2 is 1.88 kJ/mol.
The interaction of bonding donor orbital, 4, for C2-C7 with
the antibonding acceptor orbital, 333, for O1-C15 is 3.43 kJ/mol.
The interaction of bonding donor orbital, 4, for C2-C7 with
the antibonding acceptor orbital, 338, for C3-H5 is 5.56 kJ/mol.
The interaction of bonding donor orbital, 4, for C2-C7 with
the antibonding acceptor orbital, 344, for C11-H13 is 4.93 kJ/mol.
The interaction of bonding donor orbital, 5, for C2-C11 with
the antibonding acceptor orbital, 333, for O1-C15 is 6.52 kJ/mol.
The interaction of bonding donor orbital, 5, for C2-C11 with
the antibonding acceptor orbital, 334, for C2-C3 is 1.21 kJ/mol.
The interaction of bonding donor orbital, 5, for C2-C11 with
the antibonding acceptor orbital, 337, for C3-H4 is 4.93 kJ/mol.
The interaction of bonding donor orbital, 5, for C2-C11 with
the antibonding acceptor orbital, 340, for C7-H8 is 3.47 kJ/mol.
The interaction of bonding donor orbital, 6, for C3-H4 with
the antibonding acceptor orbital, 336, for C2-C11 is 11.9 kJ/mol.
The interaction of bonding donor orbital, 7, for C3-H5 with
the antibonding acceptor orbital, 332, for O1-C2 is 1.58 kJ/mol.
The interaction of bonding donor orbital, 7, for C3-H5 with
the antibonding acceptor orbital, 335, for C2-C7 is 12.9 kJ/mol.
The interaction of bonding donor orbital, 8, for C3-H6 with
the antibonding acceptor orbital, 332, for O1-C2 is 25.8 kJ/mol.
The interaction of bonding donor orbital, 9, for C7-H8 with
the antibonding acceptor orbital, 332, for O1-C2 is 1.42 kJ/mol.
The interaction of bonding donor orbital, 9, for C7-H8 with
the antibonding acceptor orbital, 336, for C2-C11 is 7.69 kJ/mol.
The interaction of bonding donor orbital, 10, for C7-H9 with
the antibonding acceptor orbital, 332, for O1-C2 is 1.67 kJ/mol.
The interaction of bonding donor orbital, 10, for C7-H9 with
the antibonding acceptor orbital, 334, for C2-C3 is 8.36 kJ/mol.
The interaction of bonding donor orbital, 11, for C7-H10 with
the antibonding acceptor orbital, 332, for O1-C2 is 12.4 kJ/mol.
The interaction of bonding donor orbital, 12, for C11-H12 with
the antibonding acceptor orbital, 332, for O1-C2 is 15.8 kJ/mol.
The interaction of bonding donor orbital, 13, for C11-H13 with
the antibonding acceptor orbital, 335, for C2-C7 is 10.7 kJ/mol.
The interaction of bonding donor orbital, 14, for C11-H14 with
the antibonding acceptor orbital, 332, for O1-C2 is 2.59 kJ/mol.
The interaction of bonding donor orbital, 14, for C11-H14 with
the antibonding acceptor orbital, 334, for C2-C3 is 10.8 kJ/mol.
The interaction of bonding donor orbital, 15, for C15-H16 with
the antibonding acceptor orbital, 332, for O1-C2 is 1.17 kJ/mol.
The interaction of bonding donor orbital, 15, for C15-H16 with
the antibonding acceptor orbital, 333, for O1-C15 is 4.60 kJ/mol.
The interaction of bonding donor orbital, 15, for C15-H16 with
the antibonding acceptor orbital, 339, for C3-H6 is 1.25 kJ/mol.
The interaction of bonding donor orbital, 16, for C15-H17 with
the antibonding acceptor orbital, 332, for O1-C2 is 3.30 kJ/mol.
The interaction of bonding donor orbital, 16, for C15-H17 with
the antibonding acceptor orbital, 333, for O1-C15 is 3.97 kJ/mol.
The interaction of bonding donor orbital, 17, for C15-H18 with
the antibonding acceptor orbital, 332, for O1-C2 is 8.91 kJ/mol.
The interaction of bonding donor orbital, 17, for C15-H18 with
the antibonding acceptor orbital, 333, for O1-C15 is 2.80 kJ/mol.
The interaction of lone pair donor orbital, 24, for O1 with
the antibonding acceptor orbital, 334, for C2-C3 is 13.0 kJ/mol.
The interaction of lone pair donor orbital, 24, for O1 with
the antibonding acceptor orbital, 336, for C2-C11 is 1.21 kJ/mol.
The interaction of lone pair donor orbital, 24, for O1 with
the antibonding acceptor orbital, 346, for C15-H16 is 6.31 kJ/mol.
The interaction of lone pair donor orbital, 24, for O1 with
the antibonding acceptor orbital, 348, for C15-H18 is 5.18 kJ/mol.
The interaction of the second lone pair donor orbital, 25, for O1 with
the antibonding acceptor orbital, 335, for C2-C7 is 11.4 kJ/mol.
The interaction of the second lone pair donor orbital, 25, for O1 with
the antibonding acceptor orbital, 336, for C2-C11 is 5.31 kJ/mol.
The interaction of the second lone pair donor orbital, 25, for O1 with
the antibonding acceptor orbital, 346, for C15-H16 is 2.84 kJ/mol.
The interaction of the second lone pair donor orbital, 25, for O1 with
the antibonding acceptor orbital, 347, for C15-H17 is 12.5 kJ/mol.
The interaction of the second lone pair donor orbital, 25, for O1 with
the antibonding acceptor orbital, 348, for C15-H18 is 2.67 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 ----- -2.670
28 ----- -2.925
27 ----- -3.552
26 ----- -4.441
25 -^--- -12.47
24 -^-v- -13.54
23 -^-v- -13.83
22 -^-v- -13.96
21 -^-v- -14.11
20 -^-v- -14.45
19 -^-v- -14.72
18 -^-v- -15.00
17 -^-v- -15.67
16 -^-v- -15.83
15 -^-v- -17.39
14 -^-v- -17.59
13 -^-v- -17.69
12 -^-v- -19.56
11 -^-v- -22.01
10 -^-v- -22.20
9 -^-v- -23.07
8 -^-v- -25.61
7 -^-v- -32.96
6 -^-v- -271.2
5 -^-v- -271.2
4 -^-v- -271.7
3 -^-v- -273.2
2 -^-v- -274.3
1 -^-v- -514.7
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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 = -272.7314864144 Hartrees
*The Lewis Strucutre calculations (NBO analysis) was done without
diffuse functions to decrease the size of the calculation.
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