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 O1-C2 with 1.9947 electrons
__has 63.60% O 1 character in a sp1.62 hybrid
__has 36.40% C 2 character in a sp1.94 hybrid
2. A bonding orbital for O1-C2 with 1.9919 electrons
__has 75.51% O 1 character in a p-pi orbital ( 99.84% p 0.16% d)
__has 24.49% C 2 character in a p-pi orbital ( 99.32% p 0.68% d)
3. A bonding orbital for C2-N3 with 1.9913 electrons
__has 36.54% C 2 character in a sp2.17 hybrid
__has 63.46% N 3 character in a sp1.82 hybrid
4. A bonding orbital for C2-C12 with 1.9878 electrons
__has 49.08% C 2 character in a sp1.86 hybrid
__has 50.92% C12 character in a sp2.74 hybrid
5. A bonding orbital for N3-C4 with 1.9898 electrons
__has 63.45% N 3 character in a sp2.12 hybrid
__has 36.55% C 4 character in a s0.94 p3 hybrid
6. A bonding orbital for N3-C8 with 1.9917 electrons
__has 62.73% N 3 character in a sp2.05 hybrid
__has 37.27% C 8 character in a s0.99 p3 hybrid
7. A bonding orbital for C4-H5 with 1.9925 electrons
__has 58.56% C 4 character in a sp2.98 hybrid
__has 41.44% H 5 character in a s orbital
8. A bonding orbital for C4-H6 with 1.9925 electrons
__has 58.56% C 4 character in a sp2.98 hybrid
__has 41.44% H 6 character in a s orbital
9. A bonding orbital for C4-H7 with 1.9910 electrons
__has 61.68% C 4 character in a sp2.84 hybrid
__has 38.32% H 7 character in a s orbital
10. A bonding orbital for C8-H9 with 1.9927 electrons
__has 58.98% C 8 character in a sp2.99 hybrid
__has 41.02% H 9 character in a s orbital
11. A bonding orbital for C8-H10 with 1.9906 electrons
__has 59.40% C 8 character in a sp2.94 hybrid
__has 40.60% H10 character in a s orbital
12. A bonding orbital for C8-H11 with 1.9926 electrons
__has 58.98% C 8 character in a sp2.99 hybrid
__has 41.02% H11 character in a s orbital
13. A bonding orbital for C12-H13 with 1.9839 electrons
__has 60.00% C12 character in a s0.96 p3 hybrid
__has 40.00% H13 character in a s orbital
14. A bonding orbital for C12-H14 with 1.9840 electrons
__has 60.00% C12 character in a s0.96 p3 hybrid
__has 40.00% H14 character in a s orbital
15. A bonding orbital for C12-H15 with 1.9915 electrons
__has 61.23% C12 character in a s0.98 p3 hybrid
__has 38.77% H15 character in a s orbital
22. A lone pair orbital for O1 with 1.9777 electrons
__made from a sp0.61 hybrid
23. A lone pair orbital for O1 with 1.9004 electrons
__made from a p3 hybrid
24. A lone pair orbital for N3 with 1.7424 electrons
__made from a p-pi orbital ( 99.98% p)
185. A antibonding orbital for O1-C2 with 0.2293 electrons
__has 24.49% O 1 character in a p-pi orbital ( 99.84% p 0.16% d)
__has 75.51% C 2 character in a p-pi orbital ( 99.32% p 0.68% d)
-With core pairs on: O 1 C 2 N 3 C 4 C 8 C12 -
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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-C12 with
the antibonding acceptor orbital, 188, for N3-C4 is 22.4 kJ/mol.
The interaction of bonding donor orbital, 9, for C4-H7 with
the antibonding acceptor orbital, 189, for N3-C8 is 20.9 kJ/mol.
The interaction of bonding donor orbital, 13, for C12-H13 with
the second antibonding acceptor orbital, 185, for O1-C2 is 21.8 kJ/mol.
The interaction of bonding donor orbital, 14, for C12-H14 with
the second antibonding acceptor orbital, 185, for O1-C2 is 21.4 kJ/mol.
The interaction of bonding donor orbital, 15, for C12-H15 with
the antibonding acceptor orbital, 186, for C2-N3 is 22.0 kJ/mol.
The interaction of the second lone pair donor orbital, 23, for O1 with
the antibonding acceptor orbital, 186, for C2-N3 is 130. kJ/mol.
The interaction of the second lone pair donor orbital, 23, for O1 with
the antibonding acceptor orbital, 187, for C2-C12 is 101. kJ/mol.
The interaction of lone pair donor orbital, 24, for N3 with
the second antibonding acceptor orbital, 185, for O1-C2 is 385. kJ/mol.
The interaction of lone pair donor orbital, 24, for N3 with
the antibonding acceptor orbital, 190, for C4-H5 is 30.2 kJ/mol.
The interaction of lone pair donor orbital, 24, for N3 with
the antibonding acceptor orbital, 191, for C4-H6 is 30.3 kJ/mol.
The interaction of lone pair donor orbital, 24, for N3 with
the antibonding acceptor orbital, 193, for C8-H9 is 33.4 kJ/mol.
The interaction of lone pair donor orbital, 24, for N3 with
the antibonding acceptor orbital, 195, for C8-H11 is 33.5 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.
28 ----- 1.535
27 ----- 1.358
26 ----- 1.102
25 ----- -0.544
24 -^-v- -5.632
23 -^-v- -5.749
22 -^-v- -8.519
21 -^-v- -9.067
20 -^-v- -9.538
19 -^-v- -9.758
18 -^-v- -9.870
17 -^-v- -9.884
16 -^-v- -10.46
15 -^-v- -11.59
14 -^-v- -11.83
13 -^-v- -12.16
12 -^-v- -13.45
11 -^-v- -16.65
10 -^-v- -17.76
9 -^-v- -18.48
8 -^-v- -23.09
7 -^-v- -25.36
6 -^-v- -266.3
5 -^-v- -266.9
4 -^-v- -267.4
3 -^-v- -268.8
2 -^-v- -378.3
1 -^-v- -505.2
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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 = -287.9278525270 Hartrees
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