dehydro-methylethylether, CH3CH2OCH2

H4H3
\ /
H1 - C2
\
H7 - C5 - H6
/
O8
\
C9 - H11
/
H10
The multiplicity is 2.

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

H1 charge= 0.097
C2 charge=-0.251
H3 charge= 0.066
H4 charge= 0.087
C5 charge= 0.148
H6 charge= 0.058
H7 charge= 0.043
O8 charge=-0.176
C9 charge=-0.476
H10 charge= 0.215
H11 charge= 0.188
with a dipole moment of 1.62713 Debye

Bond Lengths:

between H1 and C2: distance=1.103 ang___ between C2 and H3: distance=1.104 ang___
between C2 and H4: distance=1.103 ang___ between C2 and C5: distance=1.530 ang___
between C2 and O8: distance=2.467 ang___ between C5 and H6: distance=1.110 ang___
between C5 and H7: distance=1.104 ang___ between C5 and O8: distance=1.452 ang___
between C5 and C9: distance=2.381 ang___ between O8 and C9: distance=1.371 ang___
between C9 and H10: distance=1.092 ang___ between C9 and H11: distance=1.098 ang___

Bond Angles:

for H3-C2-H1: angle=108.3 deg___ for H4-C2-H1: angle=108.3 deg___
for C5-C2-H1: angle=110.4 deg___ for H6-C5-C2: angle=111.4 deg___
for H7-C5-C2: angle=111.2 deg___ for O8-C5-C2: angle=111.6 deg___
for C9-O8-C5: angle=114.9 deg___ for H10-C9-O8: angle=113.7 deg___
for H11-C9-O8: angle=118.2 deg___

Top of page.

Bond Orders (Mulliken):

between H1 and C2: order=0.984___ between C2 and H3: order=0.993___
between C2 and H4: order=0.984___ between C2 and C5: order=0.789___
between C2 and O8: order=-0.083___ between C5 and H6: order=1.012___
between C5 and H7: order=1.003___ between C5 and O8: order=0.809___
between C5 and C9: order=0.080___ between O8 and C9: order=0.819___
between C9 and H10: order=0.975___ between C9 and H11: order=0.961___

Top of page.

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. The Lewis structure is built for the up and down electrons, separately. Note that the up and down structures can be very different.

Hybridization in the Best Lewis Structure

Down Electrons

1. A bonding orbital for H1-C2 with 0.9958 electrons
__has 40.28% H 1 character in a s orbital
__has 59.72% C 2 character in a s0.96 p3 hybrid

2. A bonding orbital for C2-H3 with 0.9942 electrons
__has 59.21% C 2 character in a s0.93 p3 hybrid
__has 40.79% H 3 character in a s orbital

3. A bonding orbital for C2-H4 with 0.9958 electrons
__has 59.55% C 2 character in a s0.95 p3 hybrid
__has 40.45% H 4 character in a s orbital

4. A bonding orbital for C2-C5 with 0.9982 electrons
__has 49.96% C 2 character in a sp2.57 hybrid
__has 50.04% C 5 character in a sp2.27 hybrid

5. A bonding orbital for C5-H6 with 0.9947 electrons
__has 57.51% C 5 character in a s0.95 p3 hybrid
__has 42.49% H 6 character in a s orbital

6. A bonding orbital for C5-H7 with 0.9937 electrons
__has 58.58% C 5 character in a s0.96 p3 hybrid
__has 41.42% H 7 character in a s orbital

7. A bonding orbital for C5-O8 with 0.9958 electrons
__has 31.57% C 5 character in a s0.81 p3 hybrid
__has 68.43% O 8 character in a sp2.55 hybrid

8. A bonding orbital for O8-C9 with 0.9972 electrons
__has 68.09% O 8 character in a sp2.37 hybrid
__has 31.91% C 9 character in a sp2.73 hybrid

9. A bonding orbital for C9-H10 with 0.9952 electrons
__has 59.65% C 9 character in a sp2.00 hybrid
__has 40.35% H10 character in a s orbital

10. A bonding orbital for C9-H11 with 0.9966 electrons
__has 58.55% C 9 character in a sp2.04 hybrid
__has 41.45% H11 character in a s orbital

15. A lone pair orbital for O8 with 0.9877 electrons
__made from a sp1.85 hybrid

16. A lone pair orbital for O8 with 0.9814 electrons
__made from a s0.23 p3 hybrid

17. A lone pair orbital for C9 with 0.9947 electrons
__made from a s0.24 p3 hybrid

-With core pairs on: C 2 C 5 O 8 C 9 -

Up Electrons

1. A bonding orbital for H1-C2 with 0.9958 electrons
__has 40.31% H 1 character in a s orbital
__has 59.69% C 2 character in a s0.95 p3 hybrid

2. A bonding orbital for C2-H3 with 0.9942 electrons
__has 59.07% C 2 character in a s0.93 p3 hybrid
__has 40.93% H 3 character in a s orbital

3. A bonding orbital for C2-H4 with 0.9954 electrons
__has 59.41% C 2 character in a s0.95 p3 hybrid
__has 40.59% H 4 character in a s orbital

4. A bonding orbital for C2-C5 with 0.9974 electrons
__has 49.71% C 2 character in a sp2.55 hybrid
__has 50.29% C 5 character in a sp2.24 hybrid

5. A bonding orbital for C5-H6 with 0.9946 electrons
__has 57.62% C 5 character in a s0.94 p3 hybrid
__has 42.38% H 6 character in a s orbital

6. A bonding orbital for C5-H7 with 0.9935 electrons
__has 58.51% C 5 character in a s0.94 p3 hybrid
__has 41.49% H 7 character in a s orbital

7. A bonding orbital for C5-O8 with 0.9957 electrons
__has 32.29% C 5 character in a s0.82 p3 hybrid
__has 67.71% O 8 character in a sp2.52 hybrid

8. A bonding orbital for O8-C9 with 0.9975 electrons
__has 70.09% O 8 character in a sp2.13 hybrid
__has 29.91% C 9 character in a sp2.42 hybrid

9. A bonding orbital for O8-C9 with 0.9879 electrons
__has 90.60% O 8 character in a p3 hybrid
__has 9.40% C 9 character in a p3 hybrid

10. A bonding orbital for C9-H10 with 0.9962 electrons
__has 54.73% C 9 character in a sp1.87 hybrid
__has 45.27% H10 character in a s orbital

11. A bonding orbital for C9-H11 with 0.9966 electrons
__has 53.93% C 9 character in a sp1.79 hybrid
__has 46.07% H11 character in a s orbital

16. A lone pair orbital for O8 with 0.9847 electrons
__made from a sp1.55 hybrid

-With core pairs on: C 2 C 5 O 8 C 9 -

Top of page.

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.

Top of page.

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. Only the spin up electron orbital energies are given.

21 ----- 2.095

20 ----- 1.766
19 ----- 1.606

18 ----- 1.189


17 -^--- -3.582


16 -^-v- -7.804

15 -^-v- -8.327

14 -^-v- -8.722

13 -^-v- -9.461

12 -^-v- -10.24

11 -^-v- -10.98


10 -^-v- -12.13

9 -^-v- -12.27


8 -^-v- -14.65


7 -^-v- -16.57


6 -^-v- -18.94


5 -^-v- -26.35


4 -^-v- -266.2


3 -^-v- -267.3

2 -^-v- -267.8


1 -^-v- -507.5

Top of page.

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 = -193.7470587872 Hartrees

Top of page.

-> Return to Molecular Structure Page. -> Return to Chemistry Home Page