C5 planar

C3
\ \
| C1 = C2
/
C4
||
C5
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= 0.454
C2 charge=-0.300
C3 charge=-0.299
C4 charge= 0.441
C5 charge=-0.295
with a dipole moment of 0.19080 Debye

Bond Lengths:

between C1 and C2: distance=1.326 ang___ between C1 and C3: distance=1.435 ang___
between C1 and C4: distance=1.494 ang___ between C1 and C5: distance=2.723 ang___
between C2 and C3: distance=2.676 ang___ between C2 and C4: distance=2.723 ang___
between C2 and C5: distance=3.787 ang___ between C3 and C4: distance=1.435 ang___
between C3 and C5: distance=2.676 ang___ between C4 and C5: distance=1.326 ang___

Bond Angles:

for C3-C1-C2: angle=151.4 deg___ for C4-C1-C2: angle=149.8 deg___
for C5-C1-C2: angle=135.7 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=1.766___ between C1 and C3: order=0.858___
between C1 and C4: order=0.654___ between C1 and C5: order=0.177___
between C2 and C3: order=0.292___ between C2 and C4: order=0.177___
between C2 and C5: order=0.257___ between C3 and C4: order=0.858___
between C3 and C5: order=0.292___ between C4 and C5: order=1.767___

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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 1.9923 electrons
__has 61.28% C 1 character in a sp1.07 hybrid
__has 38.72% C 2 character in a sp2.22 hybrid

2. A bonding orbital for C1-C2 with 1.8273 electrons
__has 66.60% C 1 character in a p-pi orbital ( 99.97% p)
__has 33.40% C 2 character in a p-pi orbital ( 99.56% p 0.44% d)

3. A bonding orbital for C1-C3 with 1.9124 electrons
__has 61.68% C 1 character in a sp2.49 hybrid
__has 38.32% C 3 character in a s0.68 p3 hybrid

4. A bonding orbital for C1-C4 with 1.8659 electrons
__has 50.00% C 1 character in a s0.91 p3 hybrid
__has 50.00% C 4 character in a s0.91 p3 hybrid

5. A bonding orbital for C3-C4 with 1.9123 electrons
__has 38.31% C 3 character in a s0.68 p3 hybrid
__has 61.69% C 4 character in a sp2.49 hybrid

6. A bonding orbital for C4-C5 with 1.9923 electrons
__has 61.28% C 4 character in a sp1.07 hybrid
__has 38.72% C 5 character in a sp2.22 hybrid

7. A bonding orbital for C4-C5 with 1.8273 electrons
__has 66.59% C 4 character in a p-pi orbital ( 99.97% p)
__has 33.41% C 5 character in a p-pi orbital ( 99.56% p 0.44% d)

13. A lone pair orbital for C2 with 1.9749 electrons
__made from a sp0.44 hybrid

14. A lone pair orbital for C2 with 0.1225 electrons
__made from a p3 hybrid

15. A lone pair orbital for C3 with 1.9544 electrons
__made from a sp0.57 hybrid

16. A lone pair orbital for C3 with 0.2200 electrons
__made from a p-pi orbital ( 99.19% p 0.81% d)

17. A lone pair orbital for C5 with 1.9749 electrons
__made from a sp0.44 hybrid

18. A lone pair orbital for C5 with 0.1225 electrons
__made from a p3 hybrid

-With core pairs on: C 1 C 2 C 3 C 4 C 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, 116, for C1-C3 is 20.0 kJ/mol.

The interaction of bonding donor orbital, 1, for C1-C2 with the antibonding acceptor orbital, 117, for C1-C4 is 22.6 kJ/mol.

The interaction of the second bonding donor orbital, 2, for C1-C2 with the second lone pair acceptor orbital, 16, for C3 is 186. kJ/mol.

The interaction of the second bonding donor orbital, 2, for C1-C2 with the second antibonding acceptor orbital, 120, for C4-C5 is 60.7 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C3 with the second lone pair acceptor orbital, 14, for C2 is 51.7 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C3 with the antibonding acceptor orbital, 117, for C1-C4 is 26.1 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C3 with the antibonding acceptor orbital, 119, for C4-C5 is 97.4 kJ/mol.

The interaction of bonding donor orbital, 4, for C1-C4 with the second lone pair acceptor orbital, 14, for C2 is 49.5 kJ/mol.

The interaction of bonding donor orbital, 4, for C1-C4 with the second lone pair acceptor orbital, 18, for C5 is 49.5 kJ/mol.

The interaction of bonding donor orbital, 4, for C1-C4 with the antibonding acceptor orbital, 116, for C1-C3 is 28.1 kJ/mol.

The interaction of bonding donor orbital, 4, for C1-C4 with the antibonding acceptor orbital, 118, for C3-C4 is 28.1 kJ/mol.

The interaction of bonding donor orbital, 5, for C3-C4 with the second lone pair acceptor orbital, 18, for C5 is 51.8 kJ/mol.

The interaction of bonding donor orbital, 5, for C3-C4 with the antibonding acceptor orbital, 114, for C1-C2 is 97.4 kJ/mol.

The interaction of bonding donor orbital, 5, for C3-C4 with the antibonding acceptor orbital, 117, for C1-C4 is 26.1 kJ/mol.

The interaction of bonding donor orbital, 6, for C4-C5 with the antibonding acceptor orbital, 117, for C1-C4 is 22.6 kJ/mol.

The interaction of bonding donor orbital, 6, for C4-C5 with the antibonding acceptor orbital, 118, for C3-C4 is 20.0 kJ/mol.

The interaction of the second bonding donor orbital, 7, for C4-C5 with the second lone pair acceptor orbital, 16, for C3 is 186. kJ/mol.

The interaction of the second bonding donor orbital, 7, for C4-C5 with the second antibonding acceptor orbital, 115, for C1-C2 is 60.7 kJ/mol.

The interaction of lone pair donor orbital, 13, for C2 with the antibonding acceptor orbital, 116, for C1-C3 is 34.7 kJ/mol.

The interaction of lone pair donor orbital, 13, for C2 with the antibonding acceptor orbital, 117, for C1-C4 is 37.6 kJ/mol.

The interaction of the second lone pair donor orbital, 14, for C2 with the antibonding acceptor orbital, 117, for C1-C4 is 23.1 kJ/mol.

The interaction of the second lone pair donor orbital, 16, for C3 with the second antibonding acceptor orbital, 115, for C1-C2 is 73.7 kJ/mol.

The interaction of the second lone pair donor orbital, 16, for C3 with the second antibonding acceptor orbital, 120, for C4-C5 is 73.6 kJ/mol.

The interaction of lone pair donor orbital, 17, for C5 with the antibonding acceptor orbital, 117, for C1-C4 is 37.6 kJ/mol.

The interaction of lone pair donor orbital, 17, for C5 with the antibonding acceptor orbital, 118, for C3-C4 is 34.7 kJ/mol.

The interaction of the second lone pair donor orbital, 18, for C5 with the antibonding acceptor orbital, 117, for C1-C4 is 23.1 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.

19 ----- -1.689


18 ----- -4.243


17 ----- -5.968

16 ----- -6.237


15 -^-v- -7.985

14 -^-v- -8.168
13 -^-v- -8.245

12 -^-v- -8.410


11 -^-v- -11.62

10 -^-v- -11.88


9 -^-v- -13.11


8 -^-v- -19.12

7 -^-v- -19.85


6 -^-v- -24.63


5 -^-v- -269.3 4 -^-v- -269.3

3 -^-v- -269.8 2 -^-v- -269.8

1 -^-v- -270.4

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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 = -190.1480554297 Hartrees

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