## trans-propene-1ol, CH3CH=CHOH

 H8 H7 H6 \ | / H10 C3 - C4 \ // \ O1 - C2 H5 \ H9
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=-0.508
C2 charge=-0.050
C3 charge=-0.257
C4 charge=-0.303
H5 charge= 0.093
H6 charge= 0.114
H7 charge= 0.115
H8 charge= 0.163
H9 charge= 0.217
H10 charge= 0.415
with a dipole moment of 1.37283 Debye

## Bond Lengths:

between O1 and C2: distance=1.382 ang___ between O1 and H10: distance=0.978 ang___
between C2 and C3: distance=1.346 ang___ between C2 and C4: distance=2.517 ang___
between C2 and H9: distance=1.097 ang___ between C3 and C4: distance=1.510 ang___
between C3 and H5: distance=2.169 ang___ between C3 and H8: distance=1.102 ang___
between C3 and H9: distance=2.147 ang___ between C4 and H5: distance=1.104 ang___
between C4 and H6: distance=1.106 ang___ between C4 and H7: distance=1.106 ang___

## Bond Angles:

for C3-C2-O1: angle=126.8 deg___ for C4-C3-C2: angle=123.4 deg___
for H5-C4-C3: angle=111.1 deg___ for H6-C4-C3: angle=111.6 deg___
for H7-C4-C3: angle=111.5 deg___ for H8-C3-C2: angle=119.3 deg___
for H9-C2-O1: angle=110.4 deg___ for H10-O1-C2: angle=108.8 deg___

## Bond Orders (Mulliken):

between O1 and C2: order=0.897___ between O1 and H10: order=0.863___
between C2 and C3: order=1.854___ between C2 and C4: order=0.069___
between C2 and H9: order=0.997___ between C3 and C4: order=0.764___
between C3 and H5: order=-0.101___ between C3 and H8: order=0.915___
between C3 and H9: order=-0.070___ between C4 and H5: order=1.033___
between C4 and H6: order=0.972___ between C4 and H7: order=0.972___

## 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 1.9957 electrons
__has 66.93% O 1 character in a sp2.11 hybrid
__has 33.07% C 2 character in a sp2.69 hybrid

2. A bonding orbital for O1-H10 with 1.9894 electrons
__has 73.81% O 1 character in a s0.79 p3 hybrid
__has 26.19% H10 character in a s orbital

3. A bonding orbital for C2-C3 with 1.9930 electrons
__has 49.93% C 2 character in a sp1.32 hybrid
__has 50.07% C 3 character in a sp1.66 hybrid

4. A bonding orbital for C2-C3 with 1.9760 electrons
__has 45.45% C 2 character in a p-pi orbital ( 99.81% p 0.19% d)
__has 54.55% C 3 character in a p-pi orbital ( 99.85% p 0.15% d)

5. A bonding orbital for C2-H9 with 1.9805 electrons
__has 58.69% C 2 character in a sp2.30 hybrid
__has 41.31% H 9 character in a s orbital

6. A bonding orbital for C3-C4 with 1.9876 electrons
__has 50.41% C 3 character in a sp1.91 hybrid
__has 49.59% C 4 character in a sp2.35 hybrid

7. A bonding orbital for C3-H8 with 1.9800 electrons
__has 58.96% C 3 character in a sp2.53 hybrid
__has 41.04% H 8 character in a s orbital

8. A bonding orbital for C4-H5 with 1.9911 electrons
__has 59.38% C 4 character in a s0.93 p3 hybrid
__has 40.62% H 5 character in a s orbital

9. A bonding orbital for C4-H6 with 1.9871 electrons
__has 59.47% C 4 character in a s0.91 p3 hybrid
__has 40.53% H 6 character in a s orbital

10. A bonding orbital for C4-H7 with 1.9871 electrons
__has 59.47% C 4 character in a s0.91 p3 hybrid
__has 40.53% H 7 character in a s orbital

15. A lone pair orbital for O1 with 1.9834 electrons

16. A lone pair orbital for O1 with 1.9216 electrons
__made from a p-pi orbital ( 99.95% p)

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

#### 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, 5, for C2-H9 with the antibonding acceptor orbital, 129, for C3-H8 is 21.8 kJ/mol.

The interaction of bonding donor orbital, 6, for C3-C4 with the antibonding acceptor orbital, 123, for O1-C2 is 23.2 kJ/mol.

The interaction of bonding donor orbital, 7, for C3-H8 with the antibonding acceptor orbital, 127, for C2-H9 is 25.1 kJ/mol.

The interaction of bonding donor orbital, 8, for C4-H5 with the antibonding acceptor orbital, 129, for C3-H8 is 20.0 kJ/mol.

The interaction of lone pair donor orbital, 15, for O1 with the antibonding acceptor orbital, 125, for C2-C3 is 31.2 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 149. 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.

20 ----- 2.321

19 ----- 1.696

18 ----- 0.575

17 ----- -0.404

16 -^-v- -5.380

15 -^-v- -8.574

14 -^-v- -8.857

13 -^-v- -9.124

12 -^-v- -9.671

11 -^-v- -10.06

10 -^-v- -11.13

9 -^-v- -12.42

8 -^-v- -14.82

7 -^-v- -16.62

6 -^-v- -19.14

5 -^-v- -26.11

4 -^-v- -266.2
3 -^-v- -266.2

2 -^-v- -267.6

1 -^-v- -507.2

## 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 = -193.1979475066 Hartrees