1-dehydro-acetonitrile radical, NCCH2

H3
\
C1 - C2 = N5
/
H4
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=-0.549
C2 charge= 0.499
H3 charge= 0.247
H4 charge= 0.247
N5 charge=-0.444
with a dipole moment of 3.48281 Debye

Bond Lengths:

between C1 and C2: distance=1.381 ang___ between C1 and H3: distance=1.094 ang___
between C1 and H4: distance=1.094 ang___ between C2 and N5: distance=1.187 ang___

Bond Angles:

for H3-C1-C2: angle=120.2 deg___ for H4-C1-C2: angle=120.2 deg___
for N5-C2-C1: angle=179.8 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=1.212___ between C1 and H3: order=0.938___
between C1 and H4: order=0.937___ between C2 and N5: order=2.230___

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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.

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 0.9964 electrons
__has 50.89% C 1 character in a sp1.81 hybrid
__has 49.11% C 2 character in a sp0.93 hybrid

2. A bonding orbital for C1-H3 with 0.9878 electrons
__has 62.99% C 1 character in a sp2.09 hybrid
__has 37.01% H 3 character in a s orbital

3. A bonding orbital for C1-H4 with 0.9878 electrons
__has 62.99% C 1 character in a sp2.09 hybrid
__has 37.01% H 4 character in a s orbital

4. A bonding orbital for C2-N5 with 0.9978 electrons
__has 41.67% C 2 character in a sp1.07 hybrid
__has 58.33% N 5 character in a sp1.34 hybrid

5. A bonding orbital for C2-N5 with 0.9967 electrons
__has 30.00% C 2 character in a p-pi orbital ( 99.65% p 0.35% d)
__has 70.00% N 5 character in a p-pi orbital ( 99.68% p 0.32% d)

9. A lone pair orbital for C1 with 0.8917 electrons
__made from a p-pi orbital ( 99.95% p)

10. A lone pair orbital for C2 with 0.3035 electrons
__made from a p-pi orbital ( 99.95% p)

11. A lone pair orbital for N5 with 0.9871 electrons
__made from a sp0.73 hybrid

12. A lone pair orbital for N5 with 0.8011 electrons
__made from a p-pi orbital ( 99.73% p 0.27% d)

-With core pairs on: C 1 C 2 N 5 -

Up Electrons

1. A bonding orbital for C1-C2 with 0.9972 electrons
__has 44.70% C 1 character in a sp1.88 hybrid
__has 55.30% C 2 character in a sp0.89 hybrid

2. A bonding orbital for C1-H3 with 0.9915 electrons
__has 57.16% C 1 character in a sp2.06 hybrid
__has 42.84% H 3 character in a s orbital

3. A bonding orbital for C1-H4 with 0.9915 electrons
__has 57.16% C 1 character in a sp2.06 hybrid
__has 42.84% H 4 character in a s orbital

4. A bonding orbital for C2-N5 with 0.9986 electrons
__has 46.48% C 2 character in a sp1.11 hybrid
__has 53.52% N 5 character in a sp1.22 hybrid

5. A bonding orbital for C2-N5 with 0.9888 electrons
__has 57.95% C 2 character in a p-pi orbital ( 99.86% p 0.14% d)
__has 42.05% N 5 character in a p-pi orbital ( 99.53% p 0.47% d)

6. A bonding orbital for C2-N5 with 0.9173 electrons
__has 74.12% C 2 character in a p-pi orbital ( 99.98% p)
__has 25.88% N 5 character in a p-pi orbital ( 99.53% p 0.47% d)

11. A lone pair orbital for N5 with 0.9857 electrons
__made from a sp0.80 hybrid

-With core pairs on: C 1 C 2 N 5 -

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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 third bonding donor orbital, 6, for C2-N5 with the lone pair acceptor orbital, 10, for C1 is 159. kJ/mol.

The interaction of lone pair donor orbital, 11, for N5 with the antibonding acceptor orbital, 79, for C1-C2 is 31.7 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.

15 ----- 2.462

14 ----- 1.413

13 ----- 0.287


12 ----- -1.116


11 -^--- -6.416


10 -^-v- -8.616

9 -^-v- -9.186

8 -^-v- -9.874


7 -^-v- -12.18


6 -^-v- -13.35


5 -^-v- -19.34


4 -^-v- -22.96


3 -^-v- -268.0

2 -^-v- -268.3


1 -^-v- -378.1

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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 = -132.1366571606 Hartrees

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