trans-CH3CH=NH, trans-ethanimine

H3N7 - H8
\ //
H5 - C1 - C2
/ \
H4H6
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=-0.367
C2 charge= 0.407
H3 charge= 0.138
H4 charge= 0.106
H5 charge= 0.105
H6 charge=-0.008
N7 charge=-0.731
H8 charge= 0.348
with a dipole moment of 2.18619 Debye

Bond Lengths:

between C1 and C2: distance=1.504 ang___ between C1 and H3: distance=1.102 ang___
between C1 and H4: distance=1.106 ang___ between C1 and H5: distance=1.106 ang___
between C1 and N7: distance=2.435 ang___ between C2 and H3: distance=2.152 ang___
between C2 and H6: distance=1.112 ang___ between C2 and N7: distance=1.286 ang___
between N7 and H8: distance=1.033 ang___

Bond Angles:

for H3-C1-C2: angle=110.4 deg___ for H4-C1-C2: angle=110.3 deg___
for H5-C1-C2: angle=110.4 deg___ for H6-C2-C1: angle=115.5 deg___
for N7-C2-C1: angle=121.3 deg___ for H8-C2-C1: angle=151.5 deg___

Top of page.

Bond Orders (Mulliken):

between C1 and C2: order=0.811___ between C1 and H3: order=1.005___
between C1 and H4: order=0.971___ between C1 and H5: order=0.971___
between C1 and N7: order=-0.087___ between C2 and H3: order=-0.068___
between C2 and H6: order=0.964___ between C2 and N7: order=2.042___
between N7 and H8: order=0.897___

Top of page.

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 C1-C2 with 1.9912 electrons
__has 50.70% C 1 character in a sp2.47 hybrid
__has 49.30% C 2 character in a sp1.91 hybrid

2. A bonding orbital for C1-H3 with 1.9922 electrons
__has 60.72% C 1 character in a sp2.99 hybrid
__has 39.28% H 3 character in a s orbital

3. A bonding orbital for C1-H4 with 1.9818 electrons
__has 59.71% C 1 character in a s0.90 p3 hybrid
__has 40.29% H 4 character in a s orbital

4. A bonding orbital for C1-H5 with 1.9820 electrons
__has 59.70% C 1 character in a s0.90 p3 hybrid
__has 40.30% H 5 character in a s orbital

5. A bonding orbital for C2-H6 with 1.9882 electrons
__has 57.62% C 2 character in a sp2.36 hybrid
__has 42.38% H 6 character in a s orbital

6. A bonding orbital for C2-N7 with 1.9969 electrons
__has 41.95% C 2 character in a sp1.73 hybrid
__has 58.05% N 7 character in a sp1.48 hybrid

7. A bonding orbital for C2-N7 with 1.9887 electrons
__has 39.39% C 2 character in a p-pi orbital ( 99.71% p 0.29% d)
__has 60.61% N 7 character in a p-pi orbital ( 99.77% p 0.23% d)

8. A bonding orbital for N7-H8 with 1.9770 electrons
__has 66.41% N 7 character in a s0.81 p3 hybrid
__has 33.59% H 8 character in a s orbital

12. A lone pair orbital for N7 with 1.9590 electrons
__made from a sp1.58 hybrid

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

Top of page.

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, 101, for C2-N7 is 24.1 kJ/mol.

The interaction of bonding donor orbital, 4, for C1-H5 with the second antibonding acceptor orbital, 101, for C2-N7 is 23.8 kJ/mol.

The interaction of bonding donor orbital, 8, for N7-H8 with the antibonding acceptor orbital, 95, for C1-C2 is 44.0 kJ/mol.

The interaction of lone pair donor orbital, 12, for N7 with the antibonding acceptor orbital, 99, for C2-H6 is 62.5 kJ/mol.

Top of page.

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.

16 ----- 2.407

15 ----- 2.035

14 ----- 1.266


13 ----- -1.493


12 -^-v- -6.057


11 -^-v- -7.681


10 -^-v- -9.383

9 -^-v- -9.862

8 -^-v- -10.41


7 -^-v- -12.54


6 -^-v- -13.83


5 -^-v- -18.02


4 -^-v- -22.24


3 -^-v- -266.3


2 -^-v- -267.7


1 -^-v- -376.9

Top of page.

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 = -133.9984218856 Hartrees

Top of page.

-> Return to Molecular Structure Page. -> Return to Chemistry Home Page