N2O2, cyclic

N3 - O4
|| \ ||
O1 - N2
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

O1 charge= 0.053
N2 charge=-0.053
N3 charge=-0.053
O4 charge= 0.053
with a dipole moment of 0.00146 Debye

Bond Lengths:

between O1 and N2: distance=2.300 ang___ between O1 and N3: distance=1.166 ang___
between N2 and N3: distance=2.662 ang___ between N2 and O4: distance=1.166 ang___
between N3 and O4: distance=2.300 ang___

Bond Angles:

for N3-O1-N2: angle=94.67 deg___ for O4-O1-N2: angle=27.79 deg___

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Bond Orders (Mulliken):

between O1 and N2: order=0.273___ between O1 and N3: order=1.834___
between N2 and N3: order=0.347___ between N2 and O4: order=1.834___
between N3 and O4: order=0.273___

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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 O1-N3 with 1.9998 electrons
__has 70.72% O 1 character in a p-pi orbital ( 99.75% p 0.25% d)
__has 29.28% N 3 character in a p-pi orbital ( 99.27% p 0.73% d)

2. A bonding orbital for O1-N3 with 1.9981 electrons
__has 59.88% O 1 character in a sp2.07 hybrid
__has 40.12% N 3 character in a sp2.70 hybrid

3. A antibonding orbital for N2-N3 with 1.9891 electrons
__has 50.01% N 2 character in a p3 hybrid
__has 49.99% N 3 character in a p3 hybrid

4. A bonding orbital for N2-O4 with 1.9998 electrons
__has 29.27% N 2 character in a p-pi orbital ( 99.27% p 0.73% d)
__has 70.73% O 4 character in a p-pi orbital ( 99.75% p 0.25% d)

5. A bonding orbital for N2-O4 with 1.9981 electrons
__has 40.12% N 2 character in a sp2.70 hybrid
__has 59.88% O 4 character in a sp2.07 hybrid

10. A lone pair orbital for O1 with 1.9950 electrons
__made from a sp0.47 hybrid

11. A lone pair orbital for O1 with 1.6392 electrons
__made from a p3 hybrid

12. A lone pair orbital for N2 with 1.9975 electrons
__made from a sp0.34 hybrid

13. A lone pair orbital for N3 with 1.9975 electrons
__made from a sp0.34 hybrid

14. A lone pair orbital for O4 with 1.9950 electrons
__made from a sp0.47 hybrid

15. A lone pair orbital for O4 with 1.6393 electrons
__made from a p3 hybrid

94. A bonding orbital for N2-N3 with 0.6883 electrons
__has 49.99% N 2 character in a p3 hybrid
__has 50.01% N 3 character in a p3 hybrid

-With core pairs on: O 1 N 2 N 3 O 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 the second lone pair donor orbital, 11, for O1 with the antibonding acceptor orbital, 3, for N2-N3 is 93.3 kJ/mol.

The interaction of the second lone pair donor orbital, 11, for O1 with the bonding acceptor orbital, 94, for N2-N3 is 1199 kJ/mol.

The interaction of the second lone pair donor orbital, 15, for O4 with the antibonding acceptor orbital, 3, for N2-N3 is 93.3 kJ/mol.

The interaction of the second lone pair donor orbital, 15, for O4 with the bonding acceptor orbital, 94, for N2-N3 is 1199 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.

19 ----- 3.932


18 ----- -2.808


17 ----- -4.217

16 ----- -4.753

15 -^-v- -4.918


14 -^-v- -10.65


13 -^-v- -11.67
12 -^-v- -11.69


11 -^-v- -12.71

10 -^-v- -13.28

9 -^-v- -13.79


8 -^-v- -16.13

7 -^-v- -16.97


6 -^-v- -30.98

5 -^-v- -31.52


4 -^-v- -381.0 3 -^-v- -381.0


2 -^-v- -510.5 1 -^-v- -510.5

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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 = -259.8886332012 Hartrees

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