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.
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-O2 with 0.9994 electrons
__has 34.51% C 1 character in a sp1.20 hybrid
__has 65.49% O 2 character in a sp1.75 hybrid
2. A bonding orbital for C1-N3 with 0.9992 electrons
__has 44.31% C 1 character in a sp0.83 hybrid
__has 55.69% N 3 character in a sp2.22 hybrid
3. A bonding orbital for C1-N3 with 0.9986 electrons
__has 26.39% C 1 character in a p-pi orbital ( 99.41% p 0.59% d)
__has 73.61% N 3 character in a p-pi orbital ( 99.68% p 0.32% d)
7. A lone pair orbital for C1 with 0.2870 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)
8. A lone pair orbital for O2 with 0.9884 electrons
__made from a sp0.56 hybrid
9. A lone pair orbital for O2 with 0.9068 electrons
__made from a p-pi orbital ( 99.85% p 0.15% d)
10. A lone pair orbital for O2 with 0.8943 electrons
__made from a p-pi orbital ( 99.84% p 0.16% d)
11. A lone pair orbital for N3 with 0.9850 electrons
__made from a sp0.44 hybrid
12. A lone pair orbital for N3 with 0.8017 electrons
__made from a p-pi orbital ( 99.68% p 0.32% d)
72. A antibonding orbital for C1-N3 with 0.1007 electrons
__has 73.61% C 1 character in a p-pi orbital ( 99.41% p 0.59% d)
__has 26.39% N 3 character in a p-pi orbital ( 99.68% p 0.32% d)
-With core pairs on: C 1 O 2 N 3 -
Up Electrons
1. A bonding orbital for C1-O2 with 0.9996 electrons
__has 37.92% C 1 character in a sp1.21 hybrid
__has 62.08% O 2 character in a sp1.71 hybrid
2. A bonding orbital for C1-O2 with 0.9506 electrons
__has 55.93% C 1 character in a p-pi orbital ( 99.83% p 0.17% d)
__has 44.07% O 2 character in a p-pi orbital ( 99.67% p 0.33% d)
3. A bonding orbital for C1-N3 with 0.9995 electrons
__has 48.09% C 1 character in a sp0.82 hybrid
__has 51.91% N 3 character in a sp1.96 hybrid
4. A bonding orbital for C1-N3 with 0.9976 electrons
__has 38.92% C 1 character in a p-pi orbital ( 99.58% p 0.42% d)
__has 61.08% N 3 character in a p-pi orbital ( 99.63% p 0.37% d)
8. A lone pair orbital for O2 with 0.9875 electrons
__made from a sp0.58 hybrid
9. A lone pair orbital for O2 with 0.8952 electrons
__made from a p-pi orbital ( 99.85% p 0.15% d)
10. A lone pair orbital for N3 with 0.9846 electrons
__made from a sp0.50 hybrid
-With core pairs on: C 1 O 2 N 3 -
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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 C1-O2 with
the second lone pair acceptor orbital, 11, for N3 is 107. kJ/mol.
The interaction of lone pair donor orbital, 8, for O2 with
the antibonding acceptor orbital, 71, for C1-N3 is 37.6 kJ/mol.
The interaction of the second lone pair donor orbital, 9, for O2 with
the second antibonding acceptor orbital, 72, for C1-N3 is 231. kJ/mol.
The interaction of lone pair donor orbital, 10, for N3 with
the antibonding acceptor orbital, 69, for C1-O2 is 48.4 kJ/mol.
The interaction of the second lone pair donor orbital, 11, for N3 with
the second antibonding acceptor orbital, 70, for C1-O2 is 246. 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.
15 ----- 3.713
14 ----- 0.777
13 ----- -0.670
12 ----- -1.244
11 -^--- -8.280
10 -^-v- -9.112
9 -^-v- -10.67
8 -^-v- -12.32
7 -^-v- -12.90
6 -^-v- -13.99
5 -^-v- -24.06
4 -^-v- -28.99
3 -^-v- -270.7
2 -^-v- -379.7
1 -^-v- -509.7
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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 = -168.0681818876 Hartrees
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