N-deH-ethanimine radical, CH3CH=N•

H3H7H6
\ | /
C1 - C2
// \
N4H5
The multiplicity is 2.

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= 0.373
C2 charge=-0.465
H3 charge= 0.070
N4 charge=-0.439
H5 charge= 0.195
H6 charge= 0.133
H7 charge= 0.132
with a dipole moment of 3.15771 Debye

Bond Lengths:

between C1 and C2: distance=1.524 ang___ between C1 and H3: distance=1.117 ang___
between C1 and N4: distance=1.255 ang___ between C1 and H5: distance=2.173 ang___
between C2 and H5: distance=1.100 ang___ between C2 and H6: distance=1.104 ang___
between C2 and H7: distance=1.104 ang___

Bond Angles:

for H3-C1-C2: angle=116.0 deg___ for N4-C1-C2: angle=125.3 deg___
for H5-C2-C1: angle=110.7 deg___ for H6-C2-C1: angle=109.4 deg___
for H7-C2-C1: angle=109.5 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=0.818___ between C1 and H3: order=0.904___
between C1 and N4: order=1.718___ between C1 and H5: order=-0.052___
between C2 and H5: order=0.994___ between C2 and H6: order=0.966___
between C2 and H7: order=0.967___

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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. The Lewis structure is built for the up and down electrons, separately. Note that the up and down structures can be very different.

Hybridization in the Best Lewis Structure

Down Electrons

1. A bonding orbital for C1-C2 with 0.9979 electrons
__has 46.67% C 1 character in a sp1.83 hybrid
__has 53.33% C 2 character in a sp2.55 hybrid

2. A bonding orbital for C1-H3 with 0.9953 electrons
__has 54.36% C 1 character in a sp2.49 hybrid
__has 45.64% H 3 character in a s orbital

3. A bonding orbital for C1-N4 with 0.9988 electrons
__has 41.52% C 1 character in a sp1.72 hybrid
__has 58.48% N 4 character in a sp1.68 hybrid

4. A bonding orbital for C1-N4 with 0.9979 electrons
__has 24.19% C 1 character in a p-pi orbital ( 99.46% p 0.54% d)
__has 75.81% N 4 character in a p-pi orbital ( 99.77% p 0.23% d)

5. A bonding orbital for C2-H5 with 0.9963 electrons
__has 60.73% C 2 character in a s0.99 p3 hybrid
__has 39.27% H 5 character in a s orbital

6. A bonding orbital for C2-H6 with 0.9904 electrons
__has 60.79% C 2 character in a s0.92 p3 hybrid
__has 39.21% H 6 character in a s orbital

7. A bonding orbital for C2-H7 with 0.9906 electrons
__has 60.77% C 2 character in a s0.92 p3 hybrid
__has 39.23% H 7 character in a s orbital

11. A lone pair orbital for N4 with 0.9916 electrons
__made from a sp0.58 hybrid

12. A lone pair orbital for N4 with 0.9497 electrons
__made from a p3 hybrid

-With core pairs on: C 1 C 2 N 4 -

Up Electrons

1. A bonding orbital for C1-C2 with 0.9858 electrons
__has 53.92% C 1 character in a sp1.84 hybrid
__has 46.08% C 2 character in a sp2.83 hybrid

2. A bonding orbital for C1-H3 with 0.9764 electrons
__has 63.46% C 1 character in a sp2.48 hybrid
__has 36.54% H 3 character in a s orbital

3. A bonding orbital for C1-N4 with 0.9987 electrons
__has 47.42% C 1 character in a sp1.72 hybrid
__has 52.58% N 4 character in a sp1.39 hybrid

4. A bonding orbital for C1-N4 with 0.9912 electrons
__has 66.29% C 1 character in a p-pi orbital ( 99.83% p 0.17% d)
__has 33.71% N 4 character in a p-pi orbital ( 99.60% p 0.40% d)

5. A bonding orbital for C2-H5 with 0.9968 electrons
__has 60.04% C 2 character in a sp2.94 hybrid
__has 39.96% H 5 character in a s orbital

6. A bonding orbital for C2-H6 with 0.9941 electrons
__has 59.29% C 2 character in a s0.96 p3 hybrid
__has 40.71% H 6 character in a s orbital

7. A bonding orbital for C2-H7 with 0.9941 electrons
__has 59.30% C 2 character in a s0.96 p3 hybrid
__has 40.70% H 7 character in a s orbital

11. A lone pair orbital for N4 with 0.9907 electrons
__made from a sp0.71 hybrid

-With core pairs on: C 1 C 2 N 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 C1-C2 with the second lone pair acceptor orbital, 12, for N4 is 22.8 kJ/mol.

The interaction of bonding donor orbital, 2, for C1-H3 with the second lone pair acceptor orbital, 12, for N4 is 44.2 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. Only the spin up electron orbital energies are given.

16 ----- 2.737

15 ----- 1.950

14 ----- 1.599


13 ----- -1.471


12 -^--- -5.779


11 -^-v- -8.158

10 -^-v- -8.719


9 -^-v- -10.07

8 -^-v- -10.89

7 -^-v- -11.51


6 -^-v- -13.88


5 -^-v- -18.29


4 -^-v- -22.57


3 -^-v- -267.0

2 -^-v- -267.7


1 -^-v- -377.9

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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 = -133.3463377957 Hartrees

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