## CH3SO3-, Methane sulfonate ion

 H3 O8 O7 \ | / H5 - C1 - S2 / \ H4 O6
The ion charge is -1.

## Atomic Charges and Dipole Moment

C1 charge=-0.582
S2 charge= 1.195
H3 charge= 0.147
H4 charge= 0.148
H5 charge= 0.149
O6 charge=-0.686
O7 charge=-0.685
O8 charge=-0.686
with a dipole moment of 3.61276 Debye

## Bond Lengths:

between C1 and S2: distance=1.858 ang___ between C1 and H3: distance=1.101 ang___
between C1 and H4: distance=1.102 ang___ between C1 and H5: distance=1.101 ang___
between S2 and O6: distance=1.512 ang___ between S2 and O7: distance=1.513 ang___
between S2 and O8: distance=1.513 ang___ between O6 and O7: distance=2.541 ang___
between O6 and O8: distance=2.539 ang___ between O7 and O8: distance=2.541 ang___

## Bond Angles:

for H3-C1-S2: angle=107.9 deg___ for H4-C1-S2: angle=107.9 deg___
for H5-C1-S2: angle=107.8 deg___ for O6-S2-C1: angle=104.0 deg___
for O7-S2-C1: angle=104.2 deg___ for O8-S2-C1: angle=104.2 deg___

## Bond Orders (Mulliken):

between C1 and S2: order=0.831___ between C1 and H3: order=0.966___
between C1 and H4: order=0.966___ between C1 and H5: order=0.966___
between S2 and O6: order=1.549___ between S2 and O7: order=1.547___
between S2 and O8: order=1.548___ between O6 and O7: order=-0.140___
between O6 and O8: order=-0.140___ between O7 and O8: order=-0.139___

## 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-S2 with 1.9774 electrons
__has 56.19% C 1 character in a s0.78 p3 hybrid
__has 43.81% S 2 character in a s0.79 p3 d0.07 hybrid

2. A bonding orbital for C1-H3 with 1.9952 electrons
__has 59.81% C 1 character in a sp2.77 hybrid
__has 40.19% H 3 character in a s orbital

3. A bonding orbital for C1-H4 with 1.9952 electrons
__has 59.82% C 1 character in a sp2.77 hybrid
__has 40.18% H 4 character in a s orbital

4. A bonding orbital for C1-H5 with 1.9952 electrons
__has 59.83% C 1 character in a sp2.77 hybrid
__has 40.17% H 5 character in a s orbital

5. A bonding orbital for S2-O6 with 1.9867 electrons
__has 36.42% S 2 character in a sp2.69 d0.06 hybrid
__has 63.58% O 6 character in a s0.80 p3 hybrid

6. A bonding orbital for S2-O7 with 1.9867 electrons
__has 36.47% S 2 character in a sp2.69 d0.06 hybrid
__has 63.53% O 7 character in a s0.80 p3 hybrid

7. A bonding orbital for S2-O8 with 1.9867 electrons
__has 36.47% S 2 character in a sp2.69 d0.06 hybrid
__has 63.53% O 8 character in a s0.80 p3 hybrid

17. A lone pair orbital for O6 with 1.9857 electrons

18. A lone pair orbital for O6 with 1.8882 electrons
__made from a p-pi orbital ( 99.91% p 0.09% d)

19. A lone pair orbital for O6 with 1.8795 electrons

20. A lone pair orbital for O7 with 1.9858 electrons

21. A lone pair orbital for O7 with 1.8884 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)

22. A lone pair orbital for O7 with 1.8795 electrons

23. A lone pair orbital for O8 with 1.9858 electrons

24. A lone pair orbital for O8 with 1.8888 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)

25. A lone pair orbital for O8 with 1.8795 electrons

139. A antibonding orbital for C1-S2 with 0.1840 electrons
__has 43.81% C 1 character in a s0.78 p3 hybrid
__has 56.19% S 2 character in a s0.79 p3 d0.07 hybrid

143. A antibonding orbital for S2-O6 with 0.1303 electrons
__has 63.58% S 2 character in a sp2.69 d0.06 hybrid
__has 36.42% O 6 character in a s0.80 p3 hybrid

144. A antibonding orbital for S2-O7 with 0.1305 electrons
__has 63.53% S 2 character in a sp2.69 d0.06 hybrid
__has 36.47% O 7 character in a s0.80 p3 hybrid

145. A antibonding orbital for S2-O8 with 0.1304 electrons
__has 63.53% S 2 character in a sp2.69 d0.06 hybrid
__has 36.47% O 8 character in a s0.80 p3 hybrid

-With core pairs on: C 1 S 2 S 2 S 2 S 2 S 2 O 6 O 7 O 8 -

#### 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 the second lone pair donor orbital, 18, for O6 with the antibonding acceptor orbital, 144, for S2-O7 is 83.7 kJ/mol.

The interaction of the second lone pair donor orbital, 18, for O6 with the antibonding acceptor orbital, 145, for S2-O8 is 82.9 kJ/mol.

The interaction of the third lone pair donor orbital, 19, for O6 with the antibonding acceptor orbital, 139, for C1-S2 is 104. kJ/mol.

The interaction of the third lone pair donor orbital, 19, for O6 with the antibonding acceptor orbital, 144, for S2-O7 is 23.4 kJ/mol.

The interaction of the third lone pair donor orbital, 19, for O6 with the antibonding acceptor orbital, 145, for S2-O8 is 24.0 kJ/mol.

The interaction of the second lone pair donor orbital, 21, for O7 with the antibonding acceptor orbital, 143, for S2-O6 is 80.8 kJ/mol.

The interaction of the second lone pair donor orbital, 21, for O7 with the antibonding acceptor orbital, 145, for S2-O8 is 85.1 kJ/mol.

The interaction of the third lone pair donor orbital, 22, for O7 with the antibonding acceptor orbital, 139, for C1-S2 is 104. kJ/mol.

The interaction of the third lone pair donor orbital, 22, for O7 with the antibonding acceptor orbital, 143, for S2-O6 is 25.9 kJ/mol.

The interaction of the third lone pair donor orbital, 22, for O7 with the antibonding acceptor orbital, 145, for S2-O8 is 21.5 kJ/mol.

The interaction of the second lone pair donor orbital, 24, for O8 with the antibonding acceptor orbital, 143, for S2-O6 is 84.0 kJ/mol.

The interaction of the second lone pair donor orbital, 24, for O8 with the antibonding acceptor orbital, 144, for S2-O7 is 81.7 kJ/mol.

The interaction of the third lone pair donor orbital, 25, for O8 with the antibonding acceptor orbital, 139, for C1-S2 is 104. kJ/mol.

The interaction of the third lone pair donor orbital, 25, for O8 with the antibonding acceptor orbital, 143, for S2-O6 is 22.5 kJ/mol.

The interaction of the third lone pair donor orbital, 25, for O8 with the antibonding acceptor orbital, 144, for S2-O7 is 24.8 kJ/mol.

## 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.

29 ----- 7.010
28 ----- 6.440
27 ----- 5.824

26 ----- 5.011

25 -^-v- -0.745

24 -^-v- -1.776 23 -^-v- -1.780

22 -^-v- -1.882

21 -^-v- -2.701 20 -^-v- -2.702

19 -^-v- -5.437 18 -^-v- -5.439

17 -^-v- -6.510 16 -^-v- -6.514

15 -^-v- -6.739

14 -^-v- -9.193

13 -^-v- -13.67

12 -^-v- -18.65 11 -^-v- -18.66

10 -^-v- -22.20

9 -^-v- -154.2 8 -^-v- -154.2
7 -^-v- -154.2

6 -^-v- -207.0

5 -^-v- -262.5

4 -^-v- -500.5 3 -^-v- -500.6 2 -^-v- -500.6

1 -^-v- -2387.

## 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 = -663.9619881609 Hartrees