## FCOOH, fluoroformic acid

 F3 \ C1 = O2 // | O4 H5
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= 0.775
O2 charge=-0.525
F3 charge=-0.192
O4 charge=-0.492
H5 charge= 0.435
with a dipole moment of 2.38121 Debye

## Bond Lengths:

between C1 and O2: distance=1.348 ang___ between C1 and F3: distance=1.355 ang___
between C1 and O4: distance=1.203 ang___ between O2 and F3: distance=2.181 ang___
between O2 and O4: distance=2.301 ang___ between O2 and H5: distance=0.981 ang___
between F3 and O4: distance=2.256 ang___

## Bond Angles:

for F3-C1-O2: angle=107.6 deg___ for O4-C1-O2: angle=128.7 deg___
for H5-O2-C1: angle=106.7 deg___

## Bond Orders (Mulliken):

between C1 and O2: order=1.267___ between C1 and F3: order=1.005___
between C1 and O4: order=2.073___ between O2 and F3: order=-0.093___
between O2 and O4: order=-0.159___ between O2 and H5: order=0.834___
between F3 and O4: order=-0.066___

## 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-O2 with 1.9947 electrons
__has 33.69% C 1 character in a sp2.05 hybrid
__has 66.31% O 2 character in a sp2.55 hybrid

2. A bonding orbital for C1-F3 with 1.9939 electrons
__has 28.30% C 1 character in a sp2.60 hybrid
__has 71.70% F 3 character in a s0.96 p3 hybrid

3. A bonding orbital for C1-O4 with 1.9988 electrons
__has 35.86% C 1 character in a sp1.51 hybrid
__has 64.14% O 4 character in a sp1.72 hybrid

4. A bonding orbital for C1-O4 with 1.9982 electrons
__has 25.91% C 1 character in a p-pi orbital ( 99.24% p 0.76% d)
__has 74.09% O 4 character in a p-pi orbital ( 99.78% p 0.22% d)

5. A bonding orbital for O2-H5 with 1.9839 electrons
__has 75.64% O 2 character in a s0.88 p3 hybrid
__has 24.36% H 5 character in a s orbital

10. A lone pair orbital for O2 with 1.9769 electrons

11. A lone pair orbital for O2 with 1.8771 electrons
__made from a p-pi orbital ( 99.92% p 0.08% d)

12. A lone pair orbital for F3 with 1.9888 electrons

13. A lone pair orbital for F3 with 1.9717 electrons

14. A lone pair orbital for F3 with 1.9320 electrons
__made from a p-pi orbital ( 99.97% p)

15. A lone pair orbital for O4 with 1.9755 electrons

16. A lone pair orbital for O4 with 1.8479 electrons

99. A antibonding orbital for C1-F3 with 0.1059 electrons
__has 71.70% C 1 character in a sp2.60 hybrid
__has 28.30% F 3 character in a s0.96 p3 hybrid

101. A antibonding orbital for C1-O4 with 0.1802 electrons
__has 74.09% C 1 character in a p-pi orbital ( 99.24% p 0.76% d)
__has 25.91% O 4 character in a p-pi orbital ( 99.78% p 0.22% d)

-With core pairs on: C 1 O 2 F 3 O 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 O2-H5 with the antibonding acceptor orbital, 99, for C1-F3 is 31.0 kJ/mol.

The interaction of lone pair donor orbital, 10, for O2 with the antibonding acceptor orbital, 100, for C1-O4 is 52.3 kJ/mol.

The interaction of the second lone pair donor orbital, 11, for O2 with the second antibonding acceptor orbital, 101, for C1-O4 is 249. kJ/mol.

The interaction of the second lone pair donor orbital, 13, for F3 with the antibonding acceptor orbital, 98, for C1-O2 is 44.0 kJ/mol.

The interaction of the second lone pair donor orbital, 13, for F3 with the antibonding acceptor orbital, 100, for C1-O4 is 43.2 kJ/mol.

The interaction of the third lone pair donor orbital, 14, for F3 with the second antibonding acceptor orbital, 101, for C1-O4 is 147. kJ/mol.

The interaction of the second lone pair donor orbital, 16, for O4 with the antibonding acceptor orbital, 98, for C1-O2 is 158. kJ/mol.

The interaction of the second lone pair donor orbital, 16, for O4 with the antibonding acceptor orbital, 99, for C1-F3 is 214. 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 ----- 3.809

19 ----- 1.851

18 ----- -0.242

17 ----- -1.656

16 -^-v- -8.067

15 -^-v- -8.969

14 -^-v- -10.37

13 -^-v- -10.67

12 -^-v- -11.33

11 -^-v- -12.85

10 -^-v- -13.27

9 -^-v- -14.77

8 -^-v- -17.33

7 -^-v- -26.72

6 -^-v- -28.38

5 -^-v- -31.83

4 -^-v- -272.4

3 -^-v- -507.3

2 -^-v- -509.0

1 -^-v- -657.1

## 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 = -289.1370922994 Hartrees