ClCH2COO-, chloroacetate ion

H6Cl4
\ /
H5 - C3
\
C1 = O2
//
O7
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= 0.866
O2 charge=-0.738
C3 charge=-0.230
CL4 charge=-0.317
H5 charge= 0.099
H6 charge= 0.099
O7 charge=-0.780
with a dipole moment of 2.22706 Debye

Bond Lengths:

between C1 and O2: distance=1.254 ang___ between C1 and C3: distance=1.566 ang___
between C1 and O7: distance=1.276 ang___ between O2 and C3: distance=2.462 ang___
between O2 and O7: distance=2.302 ang___ between C3 and CL4: distance=1.888 ang___
between C3 and H5: distance=1.101 ang___ between C3 and H6: distance=1.101 ang___

Bond Angles:

for C3-C1-O2: angle=121.2 deg___ for CL4-C3-C1: angle=117.9 deg___
for H5-C3-CL4: angle=104.6 deg___ for H6-C3-CL4: angle=104.6 deg___
for O7-C1-O2: angle=131.0 deg___

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Bond Orders (Mulliken):

between C1 and O2: order=1.748___ between C1 and C3: order=0.786___
between C1 and O7: order=1.584___ between O2 and C3: order=-0.055___
between O2 and O7: order=-0.241___ between C3 and CL4: order=0.676___
between C3 and H5: order=0.974___ between C3 and H6: order=0.974___

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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-O2 with 1.9977 electrons
__has 36.11% C 1 character in a sp1.74 hybrid
__has 63.89% O 2 character in a sp1.72 hybrid

2. A bonding orbital for C1-O2 with 1.9936 electrons
__has 21.11% C 1 character in a p-pi orbital ( 99.27% p 0.73% d)
__has 78.89% O 2 character in a p-pi orbital ( 99.87% p 0.13% d)

3. A bonding orbital for C1-C3 with 1.9906 electrons
__has 43.00% C 1 character in a sp2.45 hybrid
__has 57.00% C 3 character in a sp2.34 hybrid

4. A bonding orbital for C1-O7 with 1.9935 electrons
__has 36.22% C 1 character in a sp1.87 hybrid
__has 63.78% O 7 character in a sp1.88 hybrid

5. A bonding orbital for C3-Cl4 with 1.9926 electrons
__has 38.14% C 3 character in a s0.67 p3 hybrid
__has 61.86% Cl 4 character in a s0.56 p3 hybrid

6. A bonding orbital for C3-H5 with 1.9873 electrons
__has 59.74% C 3 character in a sp2.82 hybrid
__has 40.26% H 5 character in a s orbital

7. A bonding orbital for C3-H6 with 1.9872 electrons
__has 59.73% C 3 character in a sp2.83 hybrid
__has 40.27% H 6 character in a s orbital

17. A lone pair orbital for O2 with 1.9773 electrons
__made from a sp0.57 hybrid

18. A lone pair orbital for O2 with 1.9011 electrons
__made from a p3 hybrid

19. A lone pair orbital for Cl4 with 1.9984 electrons
__made from a sp0.19 hybrid

20. A lone pair orbital for Cl4 with 1.9886 electrons
__made from a p-pi orbital ( 99.99% p)

21. A lone pair orbital for Cl4 with 1.9837 electrons
__made from a p3 hybrid

22. A lone pair orbital for O7 with 1.9784 electrons
__made from a sp0.52 hybrid

23. A lone pair orbital for O7 with 1.8978 electrons
__made from a p3 hybrid

24. A lone pair orbital for O7 with 1.6926 electrons
__made from a p3 hybrid

134. A antibonding orbital for C1-O2 with 0.3069 electrons
__has 78.89% C 1 character in a p-pi orbital ( 99.27% p 0.73% d)
__has 21.11% O 2 character in a p-pi orbital ( 99.87% p 0.13% d)

135. A antibonding orbital for C1-C3 with 0.1057 electrons
__has 57.00% C 1 character in a sp2.45 hybrid
__has 43.00% C 3 character in a sp2.34 hybrid

-With core pairs on: C 1 O 2 C 3 Cl 4 Cl 4 Cl 4 Cl 4 Cl 4 O 7 -

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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 lone pair donor orbital, 17, for O2 with the antibonding acceptor orbital, 136, for C1-O7 is 24.0 kJ/mol.

The interaction of the second lone pair donor orbital, 18, for O2 with the antibonding acceptor orbital, 135, for C1-C3 is 134. kJ/mol.

The interaction of the second lone pair donor orbital, 18, for O2 with the antibonding acceptor orbital, 136, for C1-O7 is 104. kJ/mol.

The interaction of the third lone pair donor orbital, 21, for Cl4 with the antibonding acceptor orbital, 135, for C1-C3 is 23.4 kJ/mol.

The interaction of lone pair donor orbital, 22, for O7 with the antibonding acceptor orbital, 133, for C1-O2 is 21.5 kJ/mol.

The interaction of the second lone pair donor orbital, 23, for O7 with the antibonding acceptor orbital, 133, for C1-O2 is 93.3 kJ/mol.

The interaction of the second lone pair donor orbital, 23, for O7 with the antibonding acceptor orbital, 135, for C1-C3 is 94.6 kJ/mol.

The interaction of the second lone pair donor orbital, 23, for O7 with the antibonding acceptor orbital, 137, for C3-Cl4 is 25.4 kJ/mol.

The interaction of the third lone pair donor orbital, 24, for O7 with the second antibonding acceptor orbital, 134, for C1-O2 is 626. 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.

28 ----- 7.115

27 ----- 6.098

26 ----- 4.903

25 ----- 3.497


24 -^-v- -0.531

23 -^-v- -0.772

22 -^-v- -1.172


21 -^-v- -2.812

20 -^-v- -2.951


19 -^-v- -4.260

18 -^-v- -4.623

17 -^-v- -5.595

16 -^-v- -5.838

15 -^-v- -6.811

14 -^-v- -7.661


13 -^-v- -12.35


12 -^-v- -16.19


11 -^-v- -18.32


10 -^-v- -20.42


9 -^-v- -185.4
8 -^-v- -185.4

7 -^-v- -185.7


6 -^-v- -243.8


5 -^-v- -263.3

4 -^-v- -263.8


3 -^-v- -500.0

2 -^-v- -500.1


1 -^-v- -2724.

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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 = -688.2724270871 Hartrees

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