CH3SO2Cl, Methane sulfonyl chloride

H3Cl7O8
\ | //
C1 - S2
/ | \
H4H5O6
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=-0.581
S2 charge= 0.762
H3 charge= 0.217
H4 charge= 0.219
H5 charge= 0.269
O6 charge=-0.372
CL7 charge=-0.143
O8 charge=-0.371
with a dipole moment of 4.18706 Debye

Bond Lengths:

between C1 and S2: distance=1.819 ang___ between C1 and H3: distance=1.100 ang___
between C1 and H4: distance=1.100 ang___ between C1 and H5: distance=1.103 ang___
between S2 and O6: distance=1.473 ang___ between S2 and CL7: distance=2.167 ang___
between S2 and O8: distance=1.473 ang___ between O6 and O8: distance=2.580 ang___

Bond Angles:

for H3-C1-S2: angle=108.1 deg___ for H4-C1-S2: angle=107.5 deg___
for H5-C1-S2: angle=105.4 deg___ for O6-S2-C1: angle=109.1 deg___
for CL7-S2-C1: angle=100.0 deg___ for O8-S2-C1: angle=109.8 deg___

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Bond Orders (Mulliken):

between C1 and S2: order=0.813___ between C1 and H3: order=0.932___
between C1 and H4: order=0.933___ between C1 and H5: order=0.928___
between S2 and O6: order=1.634___ between S2 and CL7: order=0.881___
between S2 and O8: order=1.629___ between O6 and O8: order=-0.164___

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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-S2 with 1.9689 electrons
__has 48.61% C 1 character in a s0.73 p3 hybrid
__has 51.39% S 2 character in a sp2.67 d0.06 hybrid

2. A bonding orbital for C1-H3 with 1.9911 electrons
__has 62.17% C 1 character in a sp2.69 hybrid
__has 37.83% H 3 character in a s orbital

3. A bonding orbital for C1-H4 with 1.9909 electrons
__has 62.19% C 1 character in a sp2.71 hybrid
__has 37.81% H 4 character in a s orbital

4. A bonding orbital for C1-H5 with 1.9870 electrons
__has 62.14% C 1 character in a sp2.76 hybrid
__has 37.86% H 5 character in a s orbital

5. A bonding orbital for S2-O6 with 1.9847 electrons
__has 36.91% S 2 character in a sp2.29 d0.05 hybrid
__has 63.09% O 6 character in a s0.87 p3 hybrid

6. A bonding orbital for S2-Cl7 with 1.9683 electrons
__has 39.93% S 2 character in a s0.52 p3 d0.10 hybrid
__has 60.07% Cl 7 character in a s0.21 p3 hybrid

7. A bonding orbital for S2-O8 with 1.9846 electrons
__has 36.97% S 2 character in a sp2.29 d0.05 hybrid
__has 63.03% O 8 character in a s0.87 p3 hybrid

21. A lone pair orbital for O6 with 1.9819 electrons
__made from a sp0.30 hybrid

22. A lone pair orbital for O6 with 1.8544 electrons
__made from a p3 hybrid

23. A lone pair orbital for O6 with 1.7899 electrons
__made from a p3 hybrid

24. A lone pair orbital for Cl7 with 1.9971 electrons
__made from a sp0.07 hybrid

25. A lone pair orbital for Cl7 with 1.9823 electrons
__made from a p-pi orbital ( 99.96% p)

26. A lone pair orbital for Cl7 with 1.9805 electrons
__made from a p3 hybrid

27. A lone pair orbital for O8 with 1.9818 electrons
__made from a sp0.30 hybrid

28. A lone pair orbital for O8 with 1.8531 electrons
__made from a p3 hybrid

29. A lone pair orbital for O8 with 1.7911 electrons
__made from a p3 hybrid

146. A antibonding orbital for C1-S2 with 0.1368 electrons
__has 51.39% C 1 character in a s0.73 p3 hybrid
__has 48.61% S 2 character in a sp2.67 d0.06 hybrid

150. A antibonding orbital for S2-O6 with 0.1105 electrons
__has 63.09% S 2 character in a sp2.29 d0.05 hybrid
__has 36.91% O 6 character in a s0.87 p3 hybrid

151. A antibonding orbital for S2-Cl7 with 0.3154 electrons
__has 60.07% S 2 character in a s0.52 p3 d0.10 hybrid
__has 39.93% Cl 7 character in a s0.21 p3 hybrid

152. A antibonding orbital for S2-O8 with 0.1105 electrons
__has 63.03% S 2 character in a sp2.29 d0.05 hybrid
__has 36.97% O 8 character in a s0.87 p3 hybrid

-With core pairs on: C 1 S 2 S 2 S 2 S 2 S 2 O 6 Cl 7 Cl 7 Cl 7 Cl 7 Cl 7 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-S2 with the antibonding acceptor orbital, 150, for S2-O6 is 21.5 kJ/mol.

The interaction of bonding donor orbital, 1, for C1-S2 with the antibonding acceptor orbital, 151, for S2-Cl7 is 24.3 kJ/mol.

The interaction of bonding donor orbital, 1, for C1-S2 with the antibonding acceptor orbital, 152, for S2-O8 is 21.6 kJ/mol.

The interaction of bonding donor orbital, 6, for S2-Cl7 with the antibonding acceptor orbital, 150, for S2-O6 is 23.9 kJ/mol.

The interaction of bonding donor orbital, 6, for S2-Cl7 with the antibonding acceptor orbital, 152, for S2-O8 is 24.0 kJ/mol.

The interaction of the second lone pair donor orbital, 22, for O6 with the antibonding acceptor orbital, 146, for C1-S2 is 87.3 kJ/mol.

The interaction of the second lone pair donor orbital, 22, for O6 with the antibonding acceptor orbital, 152, for S2-O8 is 100. kJ/mol.

The interaction of the third lone pair donor orbital, 23, for O6 with the antibonding acceptor orbital, 151, for S2-Cl7 is 231. kJ/mol.

The interaction of the third lone pair donor orbital, 23, for O6 with the antibonding acceptor orbital, 152, for S2-O8 is 23.8 kJ/mol.

The interaction of the second lone pair donor orbital, 28, for O8 with the antibonding acceptor orbital, 146, for C1-S2 is 88.2 kJ/mol.

The interaction of the second lone pair donor orbital, 28, for O8 with the antibonding acceptor orbital, 150, for S2-O6 is 100. kJ/mol.

The interaction of the third lone pair donor orbital, 29, for O8 with the antibonding acceptor orbital, 150, for S2-O6 is 23.8 kJ/mol.

The interaction of the third lone pair donor orbital, 29, for O8 with the antibonding acceptor orbital, 151, for S2-Cl7 is 230. 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.

33 ----- 0.596


32 ----- -0.243

31 ----- -0.803


30 ----- -3.754


29 -^-v- -7.866

28 -^-v- -8.305

27 -^-v- -8.508
26 -^-v- -8.575

25 -^-v- -9.225
24 -^-v- -9.245


23 -^-v- -11.53 22 -^-v- -11.53


21 -^-v- -12.56

20 -^-v- -12.88

19 -^-v- -13.48


18 -^-v- -15.96


17 -^-v- -19.91


16 -^-v- -21.39


15 -^-v- -26.04


14 -^-v- -28.73


13 -^-v- -160.8
12 -^-v- -160.8

11 -^-v- -160.9


10 -^-v- -190.7 9 -^-v- -190.7

8 -^-v- -191.1


7 -^-v- -213.7


6 -^-v- -249.2


5 -^-v- -268.5


4 -^-v- -507.6
3 -^-v- -507.6


2 -^-v- -2393.


1 -^-v- -2730.

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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 = -1048.8674735962 Hartrees

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