C3

C3 = C1 = C2
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= 0.648
C2 charge=-0.324
C3 charge=-0.324
with a dipole moment of 0.00015 Debye

Bond Lengths:

between C1 and C2: distance=1.307 ang___ between C1 and C3: distance=1.307 ang___
between C2 and C3: distance=2.614 ang___

Bond Angles:

for C3-C1-C2: angle=179.9 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=1.239___ between C1 and C3: order=1.369___
between C2 and C3: order=0.533___

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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 1.9365 electrons
__has 74.42% C 1 character in a sp0.09 hybrid
__has 25.58% C 2 character in a sp0.76 d0.05 hybrid

2. A antibonding orbital for C1-C2 with 1.6261 electrons
__has 56.74% C 1 character in a sp1.52 d0.08 hybrid
__has 43.26% C 2 character in a sp1.28 d0.25 hybrid

3. A bonding orbital for C1-C3 with 1.7355 electrons
__has 75.07% C 1 character in a sp0.73 hybrid
__has 24.93% C 3 character in a p3 hybrid

4. A antibonding orbital for C1-C3 with 1.6225 electrons
__has 22.74% C 1 character in a sp2.16 d0.21 hybrid
__has 77.26% C 3 character in a sp1.87 hybrid

5. A antibonding orbital for C2-C3 with 1.5247 electrons
__has 21.04% C 2 character in a s0.79 p3 d0.20 hybrid
__has 78.96% C 3 character in a sp0.56 d0.10 hybrid

9. A lone pair orbital for C2 with 1.9148 electrons
__made from a s orbital

10. A lone pair orbital for C3 with 0.4229 electrons
__made from a sp2.27 d0.14 hybrid

69. A bonding orbital for C1-C2 with 0.1710 electrons
__has 43.26% C 1 character in a sp1.52 d0.08 hybrid
__has 56.74% C 2 character in a sp1.28 d0.25 hybrid

-With core pairs on: C 1 C 2 C 3 -

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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, 5, for C2-C3 is 1823 kJ/mol.

The interaction of bonding donor orbital, 1, for C1-C2 with the lone pair acceptor orbital, 10, for C3 is 5982 kJ/mol.

The interaction of bonding donor orbital, 1, for C1-C2 with the antibonding acceptor orbital, 68, for C1-C2 is 422. kJ/mol.

The interaction of bonding donor orbital, 1, for C1-C2 with the antibonding acceptor orbital, 70, for C1-C3 is 919. kJ/mol.

The interaction of bonding donor orbital, 1, for C1-C2 with the bonding acceptor orbital, 72, for C2-C3 is 2537 kJ/mol.

The interaction of the second antibonding donor orbital, 2, for C1-C2 with the second antibonding acceptor orbital, 4, for C1-C3 is 1713 kJ/mol.

The interaction of the second antibonding donor orbital, 2, for C1-C2 with the antibonding acceptor orbital, 5, for C2-C3 is 2646 kJ/mol.

The interaction of the second antibonding donor orbital, 2, for C1-C2 with the lone pair acceptor orbital, 10, for C3 is 1344 kJ/mol.

The interaction of the second antibonding donor orbital, 2, for C1-C2 with the antibonding acceptor orbital, 68, for C1-C2 is 443. kJ/mol.

The interaction of the second antibonding donor orbital, 2, for C1-C2 with the second bonding acceptor orbital, 69, for C1-C2 is 1914 kJ/mol.

The interaction of the second antibonding donor orbital, 2, for C1-C2 with the antibonding acceptor orbital, 70, for C1-C3 is 1436 kJ/mol.

The interaction of the second antibonding donor orbital, 2, for C1-C2 with the bonding acceptor orbital, 72, for C2-C3 is 8951 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C3 with the second antibonding acceptor orbital, 2, for C1-C2 is 1450 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C3 with the second antibonding acceptor orbital, 4, for C1-C3 is 1939 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C3 with the antibonding acceptor orbital, 5, for C2-C3 is 78.6 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C3 with the lone pair acceptor orbital, 10, for C3 is 6140 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C3 with the antibonding acceptor orbital, 68, for C1-C2 is 1383 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C3 with the second bonding acceptor orbital, 69, for C1-C2 is 2288 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C3 with the antibonding acceptor orbital, 70, for C1-C3 is 747. kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C3 with the second bonding acceptor orbital, 71, for C1-C3 is 4530 kJ/mol.

The interaction of bonding donor orbital, 3, for C1-C3 with the bonding acceptor orbital, 72, for C2-C3 is 3105 kJ/mol.

The interaction of the second antibonding donor orbital, 4, for C1-C3 with the antibonding acceptor orbital, 5, for C2-C3 is 3543 kJ/mol.

The interaction of the second antibonding donor orbital, 4, for C1-C3 with the lone pair acceptor orbital, 10, for C3 is 1815 kJ/mol.

The interaction of the second antibonding donor orbital, 4, for C1-C3 with the antibonding acceptor orbital, 68, for C1-C2 is 406. kJ/mol.

The interaction of the second antibonding donor orbital, 4, for C1-C3 with the antibonding acceptor orbital, 70, for C1-C3 is 1057 kJ/mol.

The interaction of the second antibonding donor orbital, 4, for C1-C3 with the second bonding acceptor orbital, 71, for C1-C3 is 1392 kJ/mol.

The interaction of the second antibonding donor orbital, 4, for C1-C3 with the bonding acceptor orbital, 72, for C2-C3 is 5653 kJ/mol.

The interaction of antibonding donor orbital, 5, for C2-C3 with the lone pair acceptor orbital, 10, for C3 is 4511 kJ/mol.

The interaction of antibonding donor orbital, 5, for C2-C3 with the antibonding acceptor orbital, 68, for C1-C2 is 3280 kJ/mol.

The interaction of antibonding donor orbital, 5, for C2-C3 with the antibonding acceptor orbital, 70, for C1-C3 is 3361 kJ/mol.

The interaction of antibonding donor orbital, 5, for C2-C3 with the second bonding acceptor orbital, 71, for C1-C3 is 2792 kJ/mol.

The interaction of antibonding donor orbital, 5, for C2-C3 with the bonding acceptor orbital, 72, for C2-C3 is 7287 kJ/mol.

The interaction of lone pair donor orbital, 9, for C2 with the second antibonding acceptor orbital, 2, for C1-C2 is 144. kJ/mol.

The interaction of lone pair donor orbital, 9, for C2 with the second antibonding acceptor orbital, 4, for C1-C3 is 3273 kJ/mol.

The interaction of lone pair donor orbital, 9, for C2 with the antibonding acceptor orbital, 5, for C2-C3 is 1565 kJ/mol.

The interaction of lone pair donor orbital, 9, for C2 with the lone pair acceptor orbital, 10, for C3 is 9277 kJ/mol.

The interaction of lone pair donor orbital, 9, for C2 with the second bonding acceptor orbital, 69, for C1-C2 is 2721 kJ/mol.

The interaction of lone pair donor orbital, 9, for C2 with the antibonding acceptor orbital, 70, for C1-C3 is 1180 kJ/mol.

The interaction of lone pair donor orbital, 9, for C2 with the second bonding acceptor orbital, 71, for C1-C3 is 1581 kJ/mol.

The interaction of lone pair donor orbital, 9, for C2 with the bonding acceptor orbital, 72, for C2-C3 is 3166 kJ/mol.

The interaction of lone pair donor orbital, 10, for C3 with the antibonding acceptor orbital, 70, for C1-C3 is 1455 kJ/mol.

The interaction of lone pair donor orbital, 10, for C3 with the second bonding acceptor orbital, 71, for C1-C3 is 2194 kJ/mol.

The interaction of lone pair donor orbital, 10, for C3 with the bonding acceptor orbital, 72, for C2-C3 is 1252 kJ/mol.

The interaction of the second bonding donor orbital, 69, for C1-C2 with the second antibonding acceptor orbital, 4, for C1-C3 is 9567 kJ/mol.

The interaction of the second bonding donor orbital, 69, for C1-C2 with the antibonding acceptor orbital, 5, for C2-C3 is 6763 kJ/mol.

The interaction of the second bonding donor orbital, 69, for C1-C2 with the lone pair acceptor orbital, 10, for C3 is 9418 kJ/mol.

The interaction of the second bonding donor orbital, 69, for C1-C2 with the antibonding acceptor orbital, 70, for C1-C3 is 8029 kJ/mol.

The interaction of the second bonding donor orbital, 69, for C1-C2 with the second bonding acceptor orbital, 71, for C1-C3 is 1219 kJ/mol.

The interaction of the second bonding donor orbital, 69, for C1-C2 with the bonding acceptor orbital, 72, for C2-C3 is 2774 kJ/mol.

The interaction of the second bonding donor orbital, 71, for C1-C3 with the antibonding acceptor orbital, 70, for C1-C3 is 6092 kJ/mol.

The interaction of bonding donor orbital, 72, for C2-C3 with the antibonding acceptor orbital, 70, for C1-C3 is 867. kJ/mol.

The interaction of bonding donor orbital, 72, for C2-C3 with the second bonding acceptor orbital, 71, for C1-C3 is 1051 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.

13 ----- 0.170 12 ----- 0.169


11 ----- -5.777 10 ----- -5.778


9 -^-v- -7.986

8 -^-v- -8.799

7 -^-v- -9.782 6 -^-v- -9.782


5 -^-v- -18.22


4 -^-v- -21.05


3 -^-v- -267.8


2 -^-v- -270.0 1 -^-v- -270.0

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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 = -114.0745290781 Hartrees

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