1-dehydro-acetonitrile anion, NCCH2-

H3
\
C1 - C2 E N5
/
H4
The ion charge is -1.

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=-1.653
C2 charge= 0.855
H3 charge= 0.359
H4 charge= 0.359
N5 charge=-0.921
with a dipole moment of 1.42094 Debye

Bond Lengths:

between C1 and C2: distance=1.385 ang___ between C1 and H3: distance=1.094 ang___
between C1 and H4: distance=1.094 ang___ between C2 and N5: distance=1.200 ang___

Bond Angles:

for H3-C1-C2: angle=120.5 deg___ for H4-C1-C2: angle=120.5 deg___
for N5-C2-C1: angle=179.3 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=1.194___ between C1 and H3: order=1.002___
between C1 and H4: order=1.001___ between C2 and N5: order=2.467___

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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-C2 with 1.9928 electrons
__has 48.41% C 1 character in a sp1.82 hybrid
__has 51.59% C 2 character in a sp0.87 hybrid

2. A bonding orbital for C1-H3 with 1.9769 electrons
__has 58.91% C 1 character in a sp2.11 hybrid
__has 41.09% H 3 character in a s orbital

3. A bonding orbital for C1-H4 with 1.9769 electrons
__has 58.92% C 1 character in a sp2.10 hybrid
__has 41.08% H 4 character in a s orbital

4. A bonding orbital for C2-N5 with 1.9964 electrons
__has 43.09% C 2 character in a sp1.14 hybrid
__has 56.91% N 5 character in a sp1.14 hybrid

5. A bonding orbital for C2-N5 with 1.9926 electrons
__has 31.71% C 2 character in a p3 hybrid
__has 68.29% N 5 character in a p3 hybrid

6. A bonding orbital for C2-N5 with 1.9821 electrons
__has 44.23% C 2 character in a p-pi orbital ( 99.78% p 0.22% d)
__has 55.77% N 5 character in a p-pi orbital ( 99.66% p 0.34% d)

10. A lone pair orbital for C1 with 1.6737 electrons
__made from a p3 hybrid

11. A lone pair orbital for N5 with 1.9632 electrons
__made from a sp0.86 hybrid

83. A antibonding orbital for C2-N5 with 0.3120 electrons
__has 68.29% C 2 character in a p3 hybrid
__has 31.71% N 5 character in a p3 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 bonding donor orbital, 1, for C1-C2 with the antibonding acceptor orbital, 82, for C2-N5 is 28.8 kJ/mol.

The interaction of bonding donor orbital, 2, for C1-H3 with the antibonding acceptor orbital, 82, for C2-N5 is 31.9 kJ/mol.

The interaction of bonding donor orbital, 2, for C1-H3 with the third antibonding acceptor orbital, 84, for C2-N5 is 28.4 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-H4 with the antibonding acceptor orbital, 82, for C2-N5 is 32.0 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-H4 with the third antibonding acceptor orbital, 84, for C2-N5 is 28.3 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-N5 with the antibonding acceptor orbital, 79, for C1-C2 is 27.7 kJ/mol.

The interaction of the third bonding donor orbital, 6, for C2-N5 with the antibonding acceptor orbital, 80, for C1-H3 is 20.7 kJ/mol.

The interaction of the third bonding donor orbital, 6, for C2-N5 with the antibonding acceptor orbital, 81, for C1-H4 is 20.7 kJ/mol.

The interaction of lone pair donor orbital, 10, for C1 with the second antibonding acceptor orbital, 83, for C2-N5 is 559. kJ/mol.

The interaction of lone pair donor orbital, 11, for N5 with the antibonding acceptor orbital, 79, for C1-C2 is 78.7 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.

15 ----- 8.091
14 ----- 7.315 13 ----- 7.256

12 ----- 5.653

11 -^-v- 1.655


10 -^-v- -1.495

9 -^-v- -2.181
8 -^-v- -2.250


7 -^-v- -4.727


6 -^-v- -5.816


5 -^-v- -11.36


4 -^-v- -15.33


3 -^-v- -259.8


2 -^-v- -260.9


1 -^-v- -370.2

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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 = -132.1931903890 Hartrees

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