## H2C=CH2CN, cyanoethylene

 H3 H7 \ / C1 = C6 / \ H4 C2 \\ N5
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=-0.313
C2 charge= 0.419
H3 charge= 0.185
H4 charge= 0.199
N5 charge=-0.452
C6 charge=-0.231
H7 charge= 0.192
with a dipole moment of 4.02238 Debye

## Bond Lengths:

between C1 and C2: distance=2.443 ang___ between C1 and H3: distance=1.094 ang___
between C1 and H4: distance=1.095 ang___ between C1 and N5: distance=3.533 ang___
between C1 and C6: distance=1.349 ang___ between C2 and N5: distance=1.172 ang___
between C2 and C6: distance=1.430 ang___ between H4 and C6: distance=2.138 ang___
between N5 and C6: distance=2.602 ang___ between C6 and H7: distance=1.098 ang___

## Bond Angles:

for H3-C1-C2: angle=149.8 deg___ for H4-C1-C2: angle=92.31 deg___
for N5-C2-C1: angle=153.8 deg___ for C6-C2-C1: angle=27.55 deg___
for H7-C2-C1: angle=54.96 deg___

## Bond Orders (Mulliken):

between C1 and C2: order=0.152___ between C1 and H3: order=0.974___
between C1 and H4: order=0.968___ between C1 and N5: order=0.079___
between C1 and C6: order=1.795___ between C2 and N5: order=2.740___
between C2 and C6: order=0.842___ between H4 and C6: order=-0.052___
between N5 and C6: order=-0.104___ between C6 and H7: order=0.928___

## 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-H3 with 1.9862 electrons
__has 59.82% C 1 character in a sp2.29 hybrid
__has 40.18% H 3 character in a s orbital

2. A bonding orbital for C1-H4 with 1.9880 electrons
__has 59.99% C 1 character in a sp2.27 hybrid
__has 40.01% H 4 character in a s orbital

3. A bonding orbital for C1-C6 with 1.9877 electrons
__has 47.89% C 1 character in a sp1.54 hybrid
__has 52.11% C 6 character in a sp1.48 hybrid

4. A bonding orbital for C1-C6 with 1.9407 electrons
__has 45.09% C 1 character in a p-pi orbital ( 99.83% p 0.17% d)
__has 54.91% C 6 character in a p-pi orbital ( 99.90% p 0.10% d)

5. A bonding orbital for C2-N5 with 1.9964 electrons
__has 43.50% C 2 character in a sp1.07 hybrid
__has 56.50% N 5 character in a sp1.17 hybrid

6. A bonding orbital for C2-N5 with 1.9892 electrons
__has 44.77% C 2 character in a p3 hybrid
__has 55.23% N 5 character in a p-pi orbital ( 99.61% p 0.39% d)

7. A bonding orbital for C2-N5 with 1.9732 electrons
__has 44.28% C 2 character in a p-pi orbital ( 99.79% p 0.21% d)
__has 55.72% N 5 character in a p-pi orbital ( 99.63% p 0.37% d)

8. A bonding orbital for C2-C6 with 1.9874 electrons
__has 50.80% C 2 character in a sp0.92 hybrid
__has 49.20% C 6 character in a sp2.28 hybrid

9. A bonding orbital for C6-H7 with 1.9716 electrons
__has 61.65% C 6 character in a sp2.38 hybrid
__has 38.35% H 7 character in a s orbital

14. A lone pair orbital for N5 with 1.9714 electrons

-With core pairs on: C 1 C 2 N 5 C 6 -

#### 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-H3 with the antibonding acceptor orbital, 113, for C2-C6 is 30.8 kJ/mol.

The interaction of bonding donor orbital, 2, for C1-H4 with the antibonding acceptor orbital, 114, for C6-H7 is 23.3 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C6 with the antibonding acceptor orbital, 110, for C2-N5 is 24.3 kJ/mol.

The interaction of the second bonding donor orbital, 4, for C1-C6 with the third antibonding acceptor orbital, 112, for C2-N5 is 104. kJ/mol.

The interaction of bonding donor orbital, 5, for C2-N5 with the antibonding acceptor orbital, 113, for C2-C6 is 26.1 kJ/mol.

The interaction of the third bonding donor orbital, 7, for C2-N5 with the second antibonding acceptor orbital, 109, for C1-C6 is 42.8 kJ/mol.

The interaction of bonding donor orbital, 8, for C2-C6 with the antibonding acceptor orbital, 110, for C2-N5 is 25.1 kJ/mol.

The interaction of bonding donor orbital, 9, for C6-H7 with the antibonding acceptor orbital, 110, for C2-N5 is 21.7 kJ/mol.

The interaction of bonding donor orbital, 9, for C6-H7 with the second antibonding acceptor orbital, 111, for C2-N5 is 26.7 kJ/mol.

The interaction of lone pair donor orbital, 14, for N5 with the antibonding acceptor orbital, 113, for C2-C6 is 66.4 kJ/mol.

## 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.

18 ----- 1.414

17 ----- 1.043

16 ----- -0.849

15 ----- -3.031

14 -^-v- -7.476

13 -^-v- -8.513

12 -^-v- -8.748

11 -^-v- -9.675

10 -^-v- -10.18

9 -^-v- -11.98

8 -^-v- -13.40

7 -^-v- -16.39

6 -^-v- -20.30

5 -^-v- -22.65

4 -^-v- -267.6

3 -^-v- -267.8

2 -^-v- -268.0

1 -^-v- -377.6

## 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 = -170.8849042014 Hartrees