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 O1-C2 with 0.9916 electrons
__has 84.22% O 1 character in a s0.23 p3 hybrid
__has 15.78% C 2 character in a s0.18 p3 hybrid
2. A bonding orbital for O1-C2 with 0.9866 electrons
__has 69.78% O 1 character in a sp2.39 hybrid
__has 30.22% C 2 character in a sp2.82 hybrid
3. A bonding orbital for C2-N3 with 0.9968 electrons
__has 33.30% C 2 character in a sp2.65 hybrid
__has 66.70% N 3 character in a sp1.88 hybrid
4. A bonding orbital for C2-C9 with 0.9957 electrons
__has 51.41% C 2 character in a sp1.44 hybrid
__has 48.59% C 9 character in a sp2.93 hybrid
5. A bonding orbital for N3-C4 with 0.9960 electrons
__has 66.80% N 3 character in a sp1.77 hybrid
__has 33.20% C 4 character in a s0.91 p3 hybrid
6. A bonding orbital for N3-H8 with 0.9934 electrons
__has 74.68% N 3 character in a sp2.69 hybrid
__has 25.32% H 8 character in a s orbital
7. A bonding orbital for C4-H5 with 0.9975 electrons
__has 60.56% C 4 character in a sp2.98 hybrid
__has 39.44% H 5 character in a s orbital
8. A bonding orbital for C4-H6 with 0.9966 electrons
__has 61.04% C 4 character in a s0.98 p3 hybrid
__has 38.96% H 6 character in a s orbital
9. A bonding orbital for C4-H7 with 0.9956 electrons
__has 61.53% C 4 character in a sp2.69 hybrid
__has 38.47% H 7 character in a s orbital
10. A bonding orbital for C9-H10 with 0.9906 electrons
__has 63.52% C 9 character in a sp2.90 hybrid
__has 36.48% H10 character in a s orbital
11. A bonding orbital for C9-H11 with 0.9808 electrons
__has 63.11% C 9 character in a s0.97 p3 hybrid
__has 36.89% H11 character in a s orbital
12. A bonding orbital for C9-H12 with 0.9895 electrons
__has 61.86% C 9 character in a s0.98 p3 hybrid
__has 38.14% H12 character in a s orbital
18. A lone pair orbital for O1 with 0.9915 electrons
__made from a sp0.57 hybrid
19. A lone pair orbital for O1 with 0.9601 electrons
__made from a p3 hybrid
20. A lone pair orbital for N3 with 0.9525 electrons
__made from a s0.07 p3 hybrid
-With core pairs on: O 1 C 2 N 3 C 4 C 9 -
Up Electrons
1. A bonding orbital for O1-C2 with 0.9969 electrons
__has 61.62% O 1 character in a sp1.72 hybrid
__has 38.38% C 2 character in a sp2.16 hybrid
2. A bonding orbital for O1-C2 with 0.8671 electrons
__has 27.88% O 1 character in a p3 hybrid
__has 72.12% C 2 character in a p3 hybrid
3. A bonding orbital for C2-N3 with 0.9966 electrons
__has 38.95% C 2 character in a sp2.60 hybrid
__has 61.05% N 3 character in a sp1.86 hybrid
4. A bonding orbital for C2-C9 with 0.9956 electrons
__has 53.91% C 2 character in a sp1.45 hybrid
__has 46.09% C 9 character in a s0.99 p3 hybrid
5. A bonding orbital for N3-C4 with 0.9972 electrons
__has 62.16% N 3 character in a sp1.69 hybrid
__has 37.84% C 4 character in a s0.95 p3 hybrid
6. A bonding orbital for N3-H8 with 0.9937 electrons
__has 70.47% N 3 character in a sp2.57 hybrid
__has 29.53% H 8 character in a s orbital
7. A bonding orbital for C4-H5 with 0.9694 electrons
__has 64.66% C 4 character in a sp2.93 hybrid
__has 35.34% H 5 character in a s orbital
8. A bonding orbital for C4-H6 with 0.9797 electrons
__has 63.48% C 4 character in a s0.95 p3 hybrid
__has 36.52% H 6 character in a s orbital
9. A bonding orbital for C4-H7 with 0.9946 electrons
__has 62.03% C 4 character in a sp2.75 hybrid
__has 37.97% H 7 character in a s orbital
10. A bonding orbital for C9-H10 with 0.9926 electrons
__has 63.00% C 9 character in a sp2.86 hybrid
__has 37.00% H10 character in a s orbital
11. A bonding orbital for C9-H11 with 0.9917 electrons
__has 61.09% C 9 character in a s0.96 p3 hybrid
__has 38.91% H11 character in a s orbital
12. A bonding orbital for C9-H12 with 0.9929 electrons
__has 61.10% C 9 character in a sp2.97 hybrid
__has 38.90% H12 character in a s orbital
18. A lone pair orbital for O1 with 0.9906 electrons
__made from a sp0.58 hybrid
19. A lone pair orbital for O1 with 0.9451 electrons
__made from a p3 hybrid
20. A lone pair orbital for N3 with 0.1819 electrons
__made from a p3 hybrid
-With core pairs on: O 1 C 2 N 3 C 4 C 9 -
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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 the second bonding donor orbital, 2, for O1-C2 with
the lone pair acceptor orbital, 20, for N3 is 235. kJ/mol.
The interaction of bonding donor orbital, 7, for C4-H5 with
the lone pair acceptor orbital, 20, for N3 is 42.7 kJ/mol.
The interaction of bonding donor orbital, 8, for C4-H6 with
the lone pair acceptor orbital, 20, for N3 is 22.8 kJ/mol.
The interaction of the second lone pair donor orbital, 19, for O1 with
the antibonding acceptor orbital, 153, for C2-N3 is 71.7 kJ/mol.
The interaction of the second lone pair donor orbital, 19, for O1 with
the antibonding acceptor orbital, 154, for C2-C9 is 39.8 kJ/mol.
The interaction of antibonding donor orbital, 153, for C2-N3 with
the antibonding acceptor orbital, 154, for C2-C9 is 33.6 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.
24 ----- -3.254
23 ----- -3.527
22 ----- -4.621
21 ----- -7.959
20 -^--- -13.31
19 -^-v- -13.59
18 -^-v- -15.06
17 -^-v- -15.36
16 -^-v- -15.92
15 -^-v- -16.50
14 -^-v- -16.75
13 -^-v- -18.05
12 -^-v- -18.32
11 -^-v- -18.88
10 -^-v- -20.96
9 -^-v- -23.75
8 -^-v- -24.53
7 -^-v- -30.00
6 -^-v- -33.42
5 -^-v- -272.1
4 -^-v- -273.4
3 -^-v- -276.0
2 -^-v- -386.1
1 -^-v- -513.9
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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 = -248.2775750316 Hartrees
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