diethylether, CH3CH2OCH2CH3

H11
/
H12 - C4H15
| \ |
H8H7O3C5 - H14
\ | / /
C1 - C2H13
/ | \
H6H9H10
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=-0.451
C2 charge= 0.387
O3 charge=-0.538
C4 charge= 0.359
C5 charge=-0.447
H6 charge= 0.098
H7 charge= 0.124
H8 charge= 0.133
H9 charge=-0.041
H10 charge= 0.021
H11 charge= 0.030
H12 charge=-0.033
H13 charge= 0.133
H14 charge= 0.124
H15 charge= 0.099
with a dipole moment of 1.49881 Debye

Bond Lengths:

between C1 and C2: distance=1.536 ang___ between C1 and O3: distance=2.496 ang___
between C1 and H6: distance=1.105 ang___ between C1 and H7: distance=1.103 ang___
between C1 and H8: distance=1.105 ang___ between C1 and H9: distance=2.186 ang___
between C2 and O3: distance=1.442 ang___ between C2 and C4: distance=2.429 ang___
between C2 and H9: distance=1.110 ang___ between C2 and H10: distance=1.105 ang___
between O3 and C4: distance=1.442 ang___ between O3 and C5: distance=2.494 ang___
between C4 and C5: distance=1.536 ang___ between C4 and H11: distance=1.105 ang___
between C4 and H12: distance=1.111 ang___ between C5 and H12: distance=2.189 ang___
between C5 and H13: distance=1.104 ang___ between C5 and H14: distance=1.104 ang___
between C5 and H15: distance=1.104 ang___

Bond Angles:

for O3-C2-C1: angle=113.8 deg___ for C4-O3-C2: angle=114.7 deg___
for C5-C4-O3: angle=113.6 deg___ for H6-C1-C2: angle=109.7 deg___
for H7-C1-C2: angle=110.5 deg___ for H8-C1-C2: angle=112.2 deg___
for H9-C2-C1: angle=110.3 deg___ for H10-C2-C1: angle=110.0 deg___
for H11-C4-O3: angle=104.5 deg___ for H12-C4-O3: angle=110.5 deg___
for H13-C5-C4: angle=112.1 deg___ for H14-C5-C4: angle=110.4 deg___
for H15-C5-C4: angle=109.9 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=0.752___ between C1 and O3: order=-0.075___
between C1 and H6: order=1.003___ between C1 and H7: order=0.988___
between C1 and H8: order=0.982___ between C1 and H9: order=-0.057___
between C2 and O3: order=0.800___ between C2 and C4: order=0.138___
between C2 and H9: order=1.018___ between C2 and H10: order=1.003___
between O3 and C4: order=0.796___ between O3 and C5: order=-0.075___
between C4 and C5: order=0.750___ between C4 and H11: order=1.001___
between C4 and H12: order=1.018___ between C5 and H12: order=-0.058___
between C5 and H13: order=0.983___ between C5 and H14: order=0.988___
between C5 and H15: order=1.003___

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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 1.9960 electrons
__has 50.38% C 1 character in a sp2.53 hybrid
__has 49.62% C 2 character in a sp2.30 hybrid

2. A bonding orbital for C1-H6 with 1.9886 electrons
__has 59.17% C 1 character in a s0.92 p3 hybrid
__has 40.83% H 6 character in a s orbital

3. A bonding orbital for C1-H7 with 1.9922 electrons
__has 59.61% C 1 character in a s0.95 p3 hybrid
__has 40.39% H 7 character in a s orbital

4. A bonding orbital for C1-H8 with 1.9919 electrons
__has 58.99% C 1 character in a s0.95 p3 hybrid
__has 41.01% H 8 character in a s orbital

5. A bonding orbital for C2-O3 with 1.9928 electrons
__has 33.11% C 2 character in a s0.85 p3 hybrid
__has 66.89% O 3 character in a sp2.59 hybrid

6. A bonding orbital for C2-H9 with 1.9896 electrons
__has 57.38% C 2 character in a s0.95 p3 hybrid
__has 42.62% H 9 character in a s orbital

7. A bonding orbital for C2-H10 with 1.9860 electrons
__has 58.36% C 2 character in a s0.93 p3 hybrid
__has 41.64% H10 character in a s orbital

8. A bonding orbital for O3-C4 with 1.9927 electrons
__has 66.91% O 3 character in a sp2.60 hybrid
__has 33.09% C 4 character in a s0.85 p3 hybrid

9. A bonding orbital for C4-C5 with 1.9960 electrons
__has 49.60% C 4 character in a sp2.30 hybrid
__has 50.40% C 5 character in a sp2.53 hybrid

10. A bonding orbital for C4-H11 with 1.9859 electrons
__has 58.38% C 4 character in a s0.93 p3 hybrid
__has 41.62% H11 character in a s orbital

11. A bonding orbital for C4-H12 with 1.9897 electrons
__has 57.37% C 4 character in a s0.95 p3 hybrid
__has 42.63% H12 character in a s orbital

12. A bonding orbital for C5-H13 with 1.9918 electrons
__has 58.99% C 5 character in a s0.95 p3 hybrid
__has 41.01% H13 character in a s orbital

13. A bonding orbital for C5-H14 with 1.9921 electrons
__has 59.61% C 5 character in a s0.95 p3 hybrid
__has 40.39% H14 character in a s orbital

14. A bonding orbital for C5-H15 with 1.9887 electrons
__has 59.20% C 5 character in a s0.92 p3 hybrid
__has 40.80% H15 character in a s orbital

20. A lone pair orbital for O3 with 1.9719 electrons
__made from a sp1.24 hybrid

21. A lone pair orbital for O3 with 1.9432 electrons
__made from a p-pi orbital ( 99.97% p)

-With core pairs on: C 1 C 2 O 3 C 4 C 5 -

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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, 2, for C1-H6 with the antibonding acceptor orbital, 171, for C2-O3 is 20.4 kJ/mol.

The interaction of bonding donor orbital, 14, for C5-H15 with the antibonding acceptor orbital, 174, for O3-C4 is 20.1 kJ/mol.

The interaction of the second lone pair donor orbital, 21, for O3 with the antibonding acceptor orbital, 167, for C1-C2 is 36.3 kJ/mol.

The interaction of the second lone pair donor orbital, 21, for O3 with the antibonding acceptor orbital, 172, for C2-H9 is 26.3 kJ/mol.

The interaction of the second lone pair donor orbital, 21, for O3 with the antibonding acceptor orbital, 175, for C4-C5 is 34.8 kJ/mol.

The interaction of the second lone pair donor orbital, 21, for O3 with the antibonding acceptor orbital, 177, for C4-H12 is 28.7 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.

25 ----- 2.024

24 ----- 1.660
23 ----- 1.509

22 ----- 1.340


21 -^-v- -5.776


20 -^-v- -7.035


19 -^-v- -8.335

18 -^-v- -8.678

17 -^-v- -8.937

16 -^-v- -9.261

15 -^-v- -9.978

14 -^-v- -10.22

13 -^-v- -10.48


12 -^-v- -11.90

11 -^-v- -12.05


10 -^-v- -13.95


9 -^-v- -15.76


8 -^-v- -17.87

7 -^-v- -18.79


6 -^-v- -25.20


5 -^-v- -266.0 4 -^-v- -266.0


3 -^-v- -267.4
2 -^-v- -267.4


1 -^-v- -506.3

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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 = -233.7323986731 Hartrees

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