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 C1-N3 with 1.9971 electrons
__has 41.07% C 1 character in a sp1.67 hybrid
__has 58.93% N 3 character in a sp1.72 hybrid
2. A bonding orbital for C1-N3 with 1.9965 electrons
__has 22.06% C 1 character in a p3 hybrid
__has 77.94% N 3 character in a p3 hybrid
3. A bonding orbital for C1-H4 with 1.9830 electrons
__has 53.70% C 1 character in a sp2.55 hybrid
__has 46.30% H 4 character in a s orbital
4. A bonding orbital for C1-O5 with 1.9971 electrons
__has 35.91% C 1 character in a sp1.84 hybrid
__has 64.09% O 5 character in a sp1.78 hybrid
5. A bonding orbital for O2-H6 with 1.9986 electrons
__has 71.36% O 2 character in a s0.78 p3 hybrid
__has 28.64% H 6 character in a s orbital
6. A bonding orbital for O2-H7 with 1.9976 electrons
__has 80.25% O 2 character in a sp2.35 hybrid
__has 19.75% H 7 character in a s orbital
7. A bonding orbital for N3-H8 with 1.9822 electrons
__has 66.24% N 3 character in a s0.91 p3 hybrid
__has 33.76% H 8 character in a s orbital
12. A lone pair orbital for O2 with 1.9977 electrons
__made from a s0.28 p3 hybrid
13. A lone pair orbital for O2 with 1.9974 electrons
__made from a sp1.45 hybrid
14. A lone pair orbital for N3 with 1.8861 electrons
__made from a sp1.48 hybrid
15. A lone pair orbital for O5 with 1.9810 electrons
__made from a sp0.56 hybrid
16. A lone pair orbital for O5 with 1.9108 electrons
__made from a p3 hybrid
17. A lone pair orbital for O5 with 1.6761 electrons
__made from a p3 hybrid
115. A antibonding orbital for C1-N3 with 0.3098 electrons
__has 77.94% C 1 character in a p3 hybrid
__has 22.06% N 3 character in a p3 hybrid
-With core pairs on: C 1 O 2 N 3 O 5 -
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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, 3, for C1-H4 with
the antibonding acceptor orbital, 120, for N3-H8 is 24.6 kJ/mol.
The interaction of bonding donor orbital, 7, for N3-H8 with
the antibonding acceptor orbital, 116, for C1-H4 is 30.8 kJ/mol.
The interaction of lone pair donor orbital, 14, for N3 with
the antibonding acceptor orbital, 117, for C1-O5 is 64.3 kJ/mol.
The interaction of the second lone pair donor orbital, 16, for O5 with
the antibonding acceptor orbital, 114, for C1-N3 is 89.9 kJ/mol.
The interaction of the second lone pair donor orbital, 16, for O5 with
the antibonding acceptor orbital, 116, for C1-H4 is 117. kJ/mol.
The interaction of the third lone pair donor orbital, 17, for O5 with
the second antibonding acceptor orbital, 115, for C1-N3 is 660. kJ/mol.
The interaction of bonding donor orbital, 1, for C1-N3 with
the antibonding acceptor orbital, 119, for O2-H7 is 2.92 kJ/mol.
The interaction of lone pair donor orbital, 14, for N3 with
the antibonding acceptor orbital, 119, for O2-H7 is 238. 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.
21 ----- 7.999
20 ----- 6.654
19 ----- 5.829
18 ----- 5.014
17 -^-v- -0.143
16 -^-v- -0.380
15 -^-v- -1.499
14 -^-v- -1.680
13 -^-v- -3.833
12 -^-v- -3.929
11 -^-v- -4.989
10 -^-v- -5.430
9 -^-v- -7.169
8 -^-v- -8.845
7 -^-v- -15.46
6 -^-v- -18.90
5 -^-v- -19.25
4 -^-v- -262.8
3 -^-v- -371.0
2 -^-v- -499.8
1 -^-v- -500.5
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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 = -245.8725828710 Hartrees
* For an interesting discussion of this ion see C&ENews, 1996, Sept. 30, p 37.
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