cis-propene-1-ol, CH3CH=CHOH

H5
|
H7 - C4 - H6
\
C3 - H8
//
C2
/ \
O1H9
|
H10
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

O1 charge=-0.455
C2 charge=-0.116
C3 charge=-0.228
C4 charge= 0.057
H5 charge= 0.016
H6 charge= 0.015
H7 charge= 0.041
H8 charge= 0.112
H9 charge= 0.145
H10 charge= 0.412
with a dipole moment of 1.57890 Debye

Bond Lengths:

between O1 and C2: distance=1.391 ang___ between O1 and C3: distance=2.394 ang___
between O1 and H10: distance=0.972 ang___ between C2 and C3: distance=1.345 ang___
between C2 and C4: distance=2.531 ang___ between C2 and H9: distance=1.098 ang___
between C3 and C4: distance=1.506 ang___ between C3 and H7: distance=2.167 ang___
between C3 and H8: distance=1.096 ang___ between C4 and H5: distance=1.106 ang___
between C4 and H6: distance=1.106 ang___ between C4 and H7: distance=1.102 ang___

Bond Angles:

for C3-C2-O1: angle=122.1 deg___ for C4-C3-C2: angle=125.0 deg___
for H5-C4-C3: angle=111.1 deg___ for H6-C4-C3: angle=111.0 deg___
for H7-C4-C3: angle=111.3 deg___ for H8-C3-C2: angle=116.5 deg___
for H9-C2-O1: angle=115.9 deg___ for H10-O1-C2: angle=109.1 deg___

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Bond Orders (Mulliken):

between O1 and C2: order=0.944___ between O1 and C3: order=-0.165___
between O1 and H10: order=0.855___ between C2 and C3: order=1.929___
between C2 and C4: order=0.069___ between C2 and H9: order=0.979___
between C3 and C4: order=0.779___ between C3 and H7: order=-0.092___
between C3 and H8: order=0.927___ between C4 and H5: order=0.973___
between C4 and H6: order=0.972___ between C4 and H7: order=1.019___

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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 O1-C2 with 1.9956 electrons
__has 67.15% O 1 character in a sp2.13 hybrid
__has 32.85% C 2 character in a sp2.75 hybrid

2. A bonding orbital for O1-H10 with 1.9902 electrons
__has 73.85% O 1 character in a s0.81 p3 hybrid
__has 26.15% H10 character in a s orbital

3. A bonding orbital for C2-C3 with 1.9913 electrons
__has 50.17% C 2 character in a sp1.31 hybrid
__has 49.83% C 3 character in a sp1.67 hybrid

4. A bonding orbital for C2-C3 with 1.9785 electrons
__has 47.89% C 2 character in a p-pi orbital ( 99.85% p 0.15% d)
__has 52.11% C 3 character in a p-pi orbital ( 99.85% p 0.15% d)

5. A bonding orbital for C2-H9 with 1.9847 electrons
__has 58.23% C 2 character in a sp2.26 hybrid
__has 41.77% H 9 character in a s orbital

6. A bonding orbital for C3-C4 with 1.9902 electrons
__has 50.16% C 3 character in a sp1.91 hybrid
__has 49.84% C 4 character in a sp2.38 hybrid

7. A bonding orbital for C3-H8 with 1.9773 electrons
__has 59.46% C 3 character in a sp2.52 hybrid
__has 40.54% H 8 character in a s orbital

8. A bonding orbital for C4-H5 with 1.9858 electrons
__has 59.45% C 4 character in a s0.90 p3 hybrid
__has 40.55% H 5 character in a s orbital

9. A bonding orbital for C4-H6 with 1.9852 electrons
__has 59.46% C 4 character in a s0.90 p3 hybrid
__has 40.54% H 6 character in a s orbital

10. A bonding orbital for C4-H7 with 1.9912 electrons
__has 60.42% C 4 character in a s0.96 p3 hybrid
__has 39.58% H 7 character in a s orbital

15. A lone pair orbital for O1 with 1.9858 electrons
__made from a sp1.13 hybrid

16. A lone pair orbital for O1 with 1.9266 electrons
__made from a p-pi orbital ( 99.94% p)

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

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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 O1-H10 with the antibonding acceptor orbital, 125, for C2-C3 is 21.7 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-H9 with the antibonding acceptor orbital, 128, for C3-C4 is 26.7 kJ/mol.

The interaction of bonding donor orbital, 7, for C3-H8 with the antibonding acceptor orbital, 123, for O1-C2 is 39.0 kJ/mol.

The interaction of bonding donor orbital, 10, for C4-H7 with the antibonding acceptor orbital, 129, for C3-H8 is 20.1 kJ/mol.

The interaction of lone pair donor orbital, 15, for O1 with the antibonding acceptor orbital, 127, for C2-H9 is 24.0 kJ/mol.

The interaction of the second lone pair donor orbital, 16, for O1 with the second antibonding acceptor orbital, 126, for C2-C3 is 138. 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.

20 ----- 2.440

19 ----- 1.871

18 ----- 0.438


17 ----- -0.241


16 -^-v- -5.283


15 -^-v- -8.222

14 -^-v- -8.617

13 -^-v- -8.970

12 -^-v- -9.664

11 -^-v- -9.887


10 -^-v- -10.98


9 -^-v- -12.84


8 -^-v- -14.07


7 -^-v- -16.58


6 -^-v- -19.00


5 -^-v- -26.03


4 -^-v- -265.9

3 -^-v- -266.0


2 -^-v- -267.5


1 -^-v- -507.1

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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 = -193.1967136548 Hartrees

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