CH3NO2, Nitromethane

H3O7
\ //
H5 - C1 - N2
/ \\
H4O6
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

C1 charge=-0.470
N2 charge= 0.766
H3 charge= 0.177
H4 charge= 0.185
H5 charge= 0.179
O6 charge=-0.421
O7 charge=-0.418
with a dipole moment of 3.68650 Debye

Bond Lengths:

between C1 and N2: distance=1.511 ang___ between C1 and H3: distance=1.097 ang___
between C1 and H4: distance=1.101 ang___ between C1 and H5: distance=1.099 ang___
between N2 and O6: distance=1.242 ang___ between N2 and O7: distance=1.242 ang___

Bond Angles:

for H3-C1-N2: angle=108.3 deg___ for H4-C1-N2: angle=106.4 deg___
for H5-C1-N2: angle=108.0 deg___ for O6-N2-C1: angle=117.0 deg___
for O7-N2-C1: angle=117.2 deg___

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Bond Orders (Mulliken):

between C1 and N2: order=0.838___ between C1 and H3: order=0.966___
between C1 and H4: order=0.942___ between C1 and H5: order=0.961___
between N2 and O6: order=1.451___ between N2 and O7: order=1.453___

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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 C1-N2 with 1.9941 electrons
__has 35.44% C 1 character in a s0.78 p3 hybrid
__has 64.56% N 2 character in a sp1.99 hybrid

2. A bonding orbital for C1-H3 with 1.9909 electrons
__has 60.90% C 1 character in a sp2.71 hybrid
__has 39.10% H 3 character in a s orbital

3. A bonding orbital for C1-H4 with 1.9809 electrons
__has 60.75% C 1 character in a sp2.88 hybrid
__has 39.25% H 4 character in a s orbital

4. A bonding orbital for C1-H5 with 1.9890 electrons
__has 60.89% C 1 character in a sp2.74 hybrid
__has 39.11% H 5 character in a s orbital

5. A bonding orbital for N2-O6 with 1.9973 electrons
__has 50.64% N 2 character in a sp1.98 hybrid
__has 49.36% O 6 character in a s0.87 p3 hybrid

6. A bonding orbital for N2-O7 with 1.9973 electrons
__has 50.63% N 2 character in a sp1.98 hybrid
__has 49.37% O 7 character in a s0.87 p3 hybrid

7. A bonding orbital for N2-O7 with 1.9939 electrons
__has 33.65% N 2 character in a p-pi orbital ( 99.64% p 0.36% d)
__has 66.35% O 7 character in a p-pi orbital ( 99.84% p 0.16% d)

12. A lone pair orbital for O6 with 1.9833 electrons
__made from a sp0.29 hybrid

13. A lone pair orbital for O6 with 1.9317 electrons
__made from a p3 hybrid

14. A lone pair orbital for O6 with 1.4997 electrons
__made from a p3 hybrid

15. A lone pair orbital for O7 with 1.9833 electrons
__made from a sp0.29 hybrid

16. A lone pair orbital for O7 with 1.9326 electrons
__made from a p3 hybrid

114. A antibonding orbital for N2-O7 with 0.5103 electrons
__has 66.35% N 2 character in a p-pi orbital ( 99.64% p 0.36% d)
__has 33.65% O 7 character in a p-pi orbital ( 99.84% p 0.16% d)

-With core pairs on: C 1 N 2 O 6 O 7 -

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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 second antibonding acceptor orbital, 114, for N2-O7 is 26.9 kJ/mol.

The interaction of the second bonding donor orbital, 7, for N2-O7 with the third lone pair acceptor orbital, 14, for O6 is 53.9 kJ/mol.

The interaction of the second bonding donor orbital, 7, for N2-O7 with the second antibonding acceptor orbital, 114, for N2-O7 is 22.3 kJ/mol.

The interaction of the second lone pair donor orbital, 13, for O6 with the antibonding acceptor orbital, 108, for C1-N2 is 61.4 kJ/mol.

The interaction of the second lone pair donor orbital, 13, for O6 with the antibonding acceptor orbital, 113, for N2-O7 is 98.7 kJ/mol.

The interaction of the third lone pair donor orbital, 14, for O6 with the second antibonding acceptor orbital, 114, for N2-O7 is 1136 kJ/mol.

The interaction of the second lone pair donor orbital, 16, for O7 with the antibonding acceptor orbital, 108, for C1-N2 is 61.7 kJ/mol.

The interaction of the second lone pair donor orbital, 16, for O7 with the antibonding acceptor orbital, 112, for N2-O6 is 98.3 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.

20 ----- 2.763

19 ----- 1.537

18 ----- 0.696


17 ----- -3.549


16 -^-v- -7.075

15 -^-v- -7.556

14 -^-v- -8.137


13 -^-v- -10.75

12 -^-v- -11.21


11 -^-v- -12.95

10 -^-v- -13.45

9 -^-v- -13.86


8 -^-v- -15.45


7 -^-v- -20.35


6 -^-v- -26.59


5 -^-v- -30.90


4 -^-v- -268.2


3 -^-v- -383.8


2 -^-v- -507.7
1 -^-v- -507.7

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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 = -245.1237915154 Hartrees

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