CH=NH2 (*see note)

H3
\
N1 = C2
/ \
H4H5
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

N1 charge= 0.203
C2 charge=-0.764
H3 charge= 0.156
H4 charge= 0.104
H5 charge= 0.299
with a dipole moment of 3.57291 Debye

Bond Lengths:

between N1 and C2: distance=1.322 ang___ between N1 and H3: distance=1.027 ang___
between N1 and H4: distance=1.036 ang___ between C2 and H5: distance=1.122 ang___

Bond Angles:

for H3-N1-C2: angle=119.0 deg___ for H4-N1-C2: angle=127.2 deg___
for H5-C2-N1: angle=106.4 deg___

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Bond Orders (Mulliken):

between N1 and C2: order=1.410___ between N1 and H3: order=0.875___
between N1 and H4: order=0.869___ between C2 and H5: order=0.930___

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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.

Hybridization in the Best Lewis Structure

1. A bonding orbital for N1-C2 with 1.9996 electrons
__has 83.72% N 1 character in a p-pi orbital ( 99.96% p)
__has 16.28% C 2 character in a p-pi orbital ( 99.42% p 0.58% d)

2. A bonding orbital for N1-C2 with 1.9970 electrons
__has 67.02% N 1 character in a sp1.29 hybrid
__has 32.98% C 2 character in a sp2.45 hybrid

3. A bonding orbital for N1-H3 with 1.9915 electrons
__has 69.97% N 1 character in a sp2.59 hybrid
__has 30.03% H 3 character in a s orbital

4. A bonding orbital for N1-H4 with 1.9942 electrons
__has 69.84% N 1 character in a sp2.45 hybrid
__has 30.16% H 4 character in a s orbital

5. A bonding orbital for C2-H5 with 1.9742 electrons
__has 52.97% C 2 character in a s0.81 p3 hybrid
__has 47.03% H 5 character in a s orbital

8. A lone pair orbital for C2 with 1.9569 electrons
__made from a sp0.95 hybrid

-With core pairs on: N 1 C 2 -

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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, 5, for C2-H5 with the antibonding acceptor orbital, 64, for N1-H3 is 39.2 kJ/mol.

The interaction of lone pair donor orbital, 8, for C2 with the antibonding acceptor orbital, 65, for N1-H4 is 62.8 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.

12 ----- 3.334

11 ----- 1.959

10 ----- 0.625


9 ----- -1.891


8 -^-v- -4.546


7 -^-v- -8.894


6 -^-v- -10.32


5 -^-v- -13.64


4 -^-v- -15.92


3 -^-v- -23.32


2 -^-v- -266.7


1 -^-v- -378.9

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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 = -94.6062933353 Hartrees

*Note: This isomer is higher in energy than imine, CH2=NH

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