HON=C, (*see note)

C4
//
N3
|
H1 - O2
Tell me about the atomic charges, dipole moment, bond lengths, angles, bond orders,
molecular orbital energies, or total energy.
Tell me about the best Lewis structure.

Atomic Charges and Dipole Moment

H1 charge= 0.387
O2 charge=-0.360
N3 charge= 0.368
C4 charge=-0.395
with a dipole moment of 3.63055 Debye

Bond Lengths:

between H1 and O2: distance=0.984 ang___ between O2 and N3: distance=1.345 ang___
between O2 and C4: distance=2.529 ang___ between N3 and C4: distance=1.192 ang___

Bond Angles:

for N3-H1-O2: angle=44.06 deg___ for C4-H1-O2: angle=52.58 deg___

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Bond Orders (Mulliken):

between H1 and O2: order=0.829___ between O2 and N3: order=0.680___
between O2 and C4: order=0.061___ between N3 and C4: order=2.186___

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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 H1-O2 with 1.9845 electrons
__has 25.03% H 1 character in a s orbital
__has 74.97% O 2 character in a s0.79 p3 hybrid

2. A bonding orbital for O2-N3 with 1.9972 electrons
__has 50.87% O 2 character in a s0.76 p3 hybrid
__has 49.13% N 3 character in a sp1.72 hybrid

3. A bonding orbital for N3-C4 with 1.9967 electrons
__has 69.08% N 3 character in a sp0.64 hybrid
__has 30.92% C 4 character in a sp2.81 hybrid

4. A bonding orbital for N3-C4 with 1.9958 electrons
__has 72.34% N 3 character in a p-pi orbital ( 99.86% p 0.14% d)
__has 27.66% C 4 character in a p-pi orbital ( 99.33% p 0.67% d)

5. A bonding orbital for N3-C4 with 1.9880 electrons
__has 74.73% N 3 character in a s0.08 p3 hybrid
__has 25.27% C 4 character in a s0.07 p3 hybrid

9. A lone pair orbital for O2 with 1.9801 electrons
__made from a sp0.69 hybrid

10. A lone pair orbital for O2 with 1.9541 electrons
__made from a p-pi orbital ( 99.94% p 0.06% d)

11. A lone pair orbital for C4 with 1.9706 electrons
__made from a sp0.38 hybrid

-With core pairs on: O 2 N 3 C 4 -

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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 H1-O2 with the third antibonding acceptor orbital, 78, for N3-C4 is 29.9 kJ/mol.

The interaction of lone pair donor orbital, 9, for O2 with the antibonding acceptor orbital, 76, for N3-C4 is 46.0 kJ/mol.

The interaction of the second lone pair donor orbital, 10, for O2 with the second antibonding acceptor orbital, 77, for N3-C4 is 92.1 kJ/mol.

The interaction of lone pair donor orbital, 11, for C4 with the antibonding acceptor orbital, 75, for O2-N3 is 93.9 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.

15 ----- 1.090


14 ----- -0.582

13 ----- -0.895

12 ----- -1.428


11 -^-v- -7.607

10 -^-v- -7.801


9 -^-v- -8.874


8 -^-v- -11.84


7 -^-v- -13.10


6 -^-v- -17.24


5 -^-v- -22.89


4 -^-v- -29.36


3 -^-v- -267.9


2 -^-v- -380.1


1 -^-v- -510.0

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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 = -168.6134015021 Hartrees

* see also HOCN

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