bromoacetic acid, BrCH2COOH

H3O8
| //
C1 - C2
/ | \
BR4H5O6 - H7
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=-0.810
C2 charge= 0.860
H3 charge= 0.315
BR4 charge=-0.018
H5 charge= 0.314
O6 charge=-0.524
H7 charge= 0.406
O8 charge=-0.543
with a dipole moment of 0.46954 Debye

Bond Lengths:

between C1 and C2: distance=1.518 ang___ between C1 and H3: distance=1.101 ang___
between C1 and BR4: distance=1.981 ang___ between C1 and H5: distance=1.101 ang___
between C1 and O6: distance=2.444 ang___ between C1 and O8: distance=2.380 ang___
between C2 and BR4: distance=3.011 ang___ between C2 and O6: distance=1.357 ang___
between C2 and O8: distance=1.224 ang___ between O6 and H7: distance=0.985 ang___
between O6 and O8: distance=2.275 ang___

Bond Angles:

for H3-C1-C2: angle=108.0 deg___ for BR4-C1-C2: angle=118.1 deg___
for H5-C1-C2: angle=108.0 deg___ for O6-C2-C1: angle=116.3 deg___
for H7-C2-C1: angle=146.4 deg___ for O8-C2-C1: angle=120.1 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=0.989___ between C1 and H3: order=0.941___
between C1 and BR4: order=1.102___ between C1 and H5: order=0.941___
between C1 and O6: order=-0.228___ between C1 and O8: order=-0.071___
between C2 and BR4: order=-0.051___ between C2 and O6: order=1.127___
between C2 and O8: order=1.848___ between O6 and H7: order=0.819___
between O6 and O8: order=-0.182___

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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 1.9827 electrons
__has 51.62% C 1 character in a sp2.59 hybrid
__has 48.38% C 2 character in a sp1.68 hybrid

2. A bonding orbital for C1-H3 with 1.9801 electrons
__has 63.77% C 1 character in a sp2.72 hybrid
__has 36.23% H 3 character in a s orbital

3. A bonding orbital for C1-Br4 with 1.9904 electrons
__has 47.62% C 1 character in a s0.69 p3 hybrid
__has 52.38% Br 4 character in a s0.42 p3 hybrid

4. A bonding orbital for C1-H5 with 1.9802 electrons
__has 63.78% C 1 character in a sp2.72 hybrid
__has 36.22% H 5 character in a s orbital

5. A bonding orbital for C2-O6 with 1.9945 electrons
__has 30.78% C 2 character in a sp2.50 hybrid
__has 69.22% O 6 character in a sp2.07 hybrid

6. A bonding orbital for C2-O8 with 1.9955 electrons
__has 25.45% C 2 character in a p3 hybrid
__has 74.55% O 8 character in a p3 hybrid

7. A bonding orbital for C2-O8 with 1.9941 electrons
__has 33.95% C 2 character in a sp1.89 hybrid
__has 66.05% O 8 character in a sp1.54 hybrid

8. A bonding orbital for O6-H7 with 1.9870 electrons
__has 77.30% O 6 character in a s0.87 p3 hybrid
__has 22.70% H 7 character in a s orbital

27. A lone pair orbital for Br4 with 1.9977 electrons
__made from a sp0.14 hybrid

28. A lone pair orbital for Br4 with 1.9894 electrons
__made from a p-pi orbital ( 99.98% p)

29. A lone pair orbital for Br4 with 1.9817 electrons
__made from a p3 hybrid

30. A lone pair orbital for O6 with 1.9818 electrons
__made from a sp1.21 hybrid

31. A lone pair orbital for O6 with 1.8670 electrons
__made from a p-pi orbital ( 99.85% p 0.15% d)

32. A lone pair orbital for O8 with 1.9805 electrons
__made from a sp0.64 hybrid

33. A lone pair orbital for O8 with 1.8839 electrons
__made from a p-pi orbital ( 99.78% p 0.22% d)

123. A antibonding orbital for C2-O8 with 0.1520 electrons
__has 74.55% C 2 character in a p3 hybrid
__has 25.45% O 8 character in a p3 hybrid

-With core pairs on: C 1 C 2 Br 4 Br 4 Br 4 Br 4 Br 4 Br 4 Br 4 Br 4 Br 4 Br 4 Br 4 Br 4 Br 4 Br 4 O 6 O 8 -

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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, 125, for O6-H7 is 21.5 kJ/mol.

The interaction of bonding donor orbital, 2, for C1-H3 with the antibonding acceptor orbital, 123, for C2-O8 is 24.1 kJ/mol.

The interaction of bonding donor orbital, 4, for C1-H5 with the antibonding acceptor orbital, 123, for C2-O8 is 23.5 kJ/mol.

The interaction of bonding donor orbital, 8, for O6-H7 with the antibonding acceptor orbital, 118, for C1-C2 is 28.8 kJ/mol.

The interaction of the third lone pair donor orbital, 29, for Br4 with the antibonding acceptor orbital, 118, for C1-C2 is 24.3 kJ/mol.

The interaction of lone pair donor orbital, 30, for O6 with the second antibonding acceptor orbital, 124, for C2-O8 is 41.0 kJ/mol.

The interaction of the second lone pair donor orbital, 31, for O6 with the antibonding acceptor orbital, 123, for C2-O8 is 261. kJ/mol.

The interaction of the second lone pair donor orbital, 33, for O8 with the antibonding acceptor orbital, 118, for C1-C2 is 91.0 kJ/mol.

The interaction of the second lone pair donor orbital, 33, for O8 with the antibonding acceptor orbital, 122, for C2-O6 is 162. 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.

37 ----- 1.603

36 ----- 0.381


35 ----- -1.817

34 ----- -1.918


33 -^-v- -6.853

32 -^-v- -7.008

31 -^-v- -7.561

30 -^-v- -8.467


29 -^-v- -10.12

28 -^-v- -10.32

27 -^-v- -10.57


26 -^-v- -12.29

25 -^-v- -12.48
24 -^-v- -12.55


23 -^-v- -15.86


22 -^-v- -18.15


21 -^-v- -20.70


20 -^-v- -25.87


19 -^-v- -28.21


18 -^-v- -68.38 17 -^-v- -68.38

16 -^-v- -68.71 15 -^-v- -68.71

14 -^-v- -68.83


13 -^-v- -171.6 12 -^-v- -171.6

11 -^-v- -172.1


10 -^-v- -229.1


9 -^-v- -268.6


8 -^-v- -270.6


7 -^-v- -506.9


6 -^-v- -508.4


5 -^-v- -1517. 4 -^-v- -1517.
3 -^-v- -1517.


2 -^-v- -1680.


1 -^-v- -13067

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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 = -2802.5606925866 Hartrees

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