1,1-dibromoethylene

H3BR6
\ /
C1 = C2
/ \
H4BR5
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=-0.191
C2 charge=-0.251
H3 charge= 0.170
H4 charge= 0.170
BR5 charge= 0.049
BR6 charge= 0.051
with a dipole moment of 1.31182 Debye

Bond Lengths:

between C1 and C2: distance=1.336 ang___ between C1 and H3: distance=1.094 ang___
between C1 and H4: distance=1.094 ang___ between C1 and BR5: distance=2.871 ang___
between C1 and BR6: distance=2.872 ang___ between C2 and BR5: distance=1.922 ang___
between C2 and BR6: distance=1.921 ang___

Bond Angles:

for H3-C1-C2: angle=120.4 deg___ for H4-C1-C2: angle=120.5 deg___
for BR5-C2-C1: angle=122.5 deg___ for BR6-C2-C1: angle=122.7 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=1.873___ between C1 and H3: order=0.896___
between C1 and H4: order=0.896___ between C1 and BR5: order=0.096___
between C1 and BR6: order=0.097___ between C2 and BR5: order=1.024___
between C2 and BR6: order=1.025___

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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.

Hybridization in the Best Lewis Structure

1. A bonding orbital for C1-C2 with 1.9968 electrons
__has 49.44% C 1 character in a sp1.60 hybrid
__has 50.56% C 2 character in a sp1.12 hybrid

2. A bonding orbital for C1-C2 with 1.9953 electrons
__has 45.24% C 1 character in a p-pi orbital ( 99.74% p 0.26% d)
__has 54.76% C 2 character in a p-pi orbital ( 99.86% p 0.14% d)

3. A bonding orbital for C1-H3 with 1.9730 electrons
__has 61.92% C 1 character in a sp2.24 hybrid
__has 38.08% H 3 character in a s orbital

4. A bonding orbital for C1-H4 with 1.9730 electrons
__has 61.93% C 1 character in a sp2.23 hybrid
__has 38.07% H 4 character in a s orbital

5. A bonding orbital for C2-Br5 with 1.9846 electrons
__has 51.12% C 2 character in a sp2.75 hybrid
__has 48.88% Br 5 character in a s0.48 p3 hybrid

6. A bonding orbital for C2-Br6 with 1.9846 electrons
__has 51.16% C 2 character in a sp2.74 hybrid
__has 48.84% Br 6 character in a s0.48 p3 hybrid

37. A lone pair orbital for Br5 with 1.9897 electrons
__made from a sp0.23 hybrid

38. A lone pair orbital for Br5 with 1.9700 electrons
__made from a s0.17 p3 hybrid

39. A lone pair orbital for Br5 with 1.9541 electrons
__made from a p-pi orbital ( 99.97% p)

40. A lone pair orbital for Br6 with 1.9896 electrons
__made from a sp0.23 hybrid

41. A lone pair orbital for Br6 with 1.9697 electrons
__made from a s0.17 p3 hybrid

42. A lone pair orbital for Br6 with 1.9538 electrons
__made from a p-pi orbital ( 99.97% p)

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

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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, 3, for C1-H3 with the antibonding acceptor orbital, 115, for C2-Br5 is 51.4 kJ/mol.

The interaction of bonding donor orbital, 4, for C1-H4 with the antibonding acceptor orbital, 116, for C2-Br6 is 51.5 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-Br5 with the antibonding acceptor orbital, 113, for C1-H3 is 20.1 kJ/mol.

The interaction of the second lone pair donor orbital, 38, for Br5 with the antibonding acceptor orbital, 116, for C2-Br6 is 43.5 kJ/mol.

The interaction of the third lone pair donor orbital, 39, for Br5 with the second antibonding acceptor orbital, 112, for C1-C2 is 66.4 kJ/mol.

The interaction of lone pair donor orbital, 40, for Br6 with the antibonding acceptor orbital, 111, for C1-C2 is 19.9 kJ/mol.

The interaction of the second lone pair donor orbital, 41, for Br6 with the antibonding acceptor orbital, 115, for C2-Br5 is 43.9 kJ/mol.

The interaction of the third lone pair donor orbital, 42, for Br6 with the second antibonding acceptor orbital, 112, for C1-C2 is 66.9 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.

46 ----- 1.955


45 ----- -0.996

44 ----- -1.938

43 ----- -2.294


42 -^-v- -6.536

41 -^-v- -7.118

40 -^-v- -7.500

39 -^-v- -7.879


38 -^-v- -9.474

37 -^-v- -9.611


36 -^-v- -11.42

35 -^-v- -12.09


34 -^-v- -13.97


33 -^-v- -18.56


32 -^-v- -19.91


31 -^-v- -21.75


30 -^-v- -68.81 29 -^-v- -68.81 28 -^-v- -68.82 27 -^-v- -68.82

26 -^-v- -69.13 25 -^-v- -69.14 24 -^-v- -69.14 23 -^-v- -69.15

22 -^-v- -69.26 21 -^-v- -69.27


20 -^-v- -172.0 19 -^-v- -172.0 18 -^-v- -172.1 17 -^-v- -172.1

16 -^-v- -172.5 15 -^-v- -172.5


14 -^-v- -229.5 13 -^-v- -229.5


12 -^-v- -267.1


11 -^-v- -269.6


10 -^-v- -1518. 9 -^-v- -1518. 8 -^-v- -1518. 7 -^-v- -1518.
6 -^-v- -1518. 5 -^-v- -1518.


4 -^-v- -1681. 3 -^-v- -1681.


2 -^-v- -13067
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 = -5225.3908671299 Hartrees

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