formamide, CH2CONH2

O3H6
\\ /
C1 - N2
/ \
H4H5
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= 0.552
N2 charge=-0.879
O3 charge=-0.517
H4 charge= 0.024
H5 charge= 0.390
H6 charge= 0.428
with a dipole moment of 4.12863 Debye

Bond Lengths:

between C1 and N2: distance=1.371 ang___ between C1 and O3: distance=1.230 ang___
between C1 and H4: distance=1.118 ang___ between N2 and O3: distance=2.303 ang___
between N2 and H4: distance=2.075 ang___ between N2 and H5: distance=1.017 ang___
between N2 and H6: distance=1.020 ang___ between O3 and H4: distance=2.064 ang___

Bond Angles:

for O3-C1-N2: angle=124.4 deg___ for H4-C1-N2: angle=112.5 deg___
for H5-N2-C1: angle=121.2 deg___ for H6-N2-C1: angle=119.0 deg___

Top of page.

Bond Orders (Mulliken):

between C1 and N2: order=1.031___ between C1 and O3: order=1.843___
between C1 and H4: order=0.993___ between N2 and O3: order=-0.103___
between N2 and H4: order=-0.115___ between N2 and H5: order=0.875___
between N2 and H6: order=0.886___ between O3 and H4: order=0.066___

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. 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-N2 with 1.9971 electrons
__has 37.65% C 1 character in a sp2.01 hybrid
__has 62.35% N 2 character in a sp1.64 hybrid

2. A bonding orbital for C1-O3 with 1.9979 electrons
__has 25.83% C 1 character in a p3 hybrid
__has 74.17% O 3 character in a p3 hybrid

3. A bonding orbital for C1-O3 with 1.9974 electrons
__has 36.26% C 1 character in a sp1.81 hybrid
__has 63.74% O 3 character in a sp1.65 hybrid

4. A bonding orbital for C1-H4 with 1.9866 electrons
__has 56.54% C 1 character in a sp2.16 hybrid
__has 43.46% H 4 character in a s orbital

5. A bonding orbital for N2-H5 with 1.9926 electrons
__has 70.05% N 2 character in a sp2.22 hybrid
__has 29.95% H 5 character in a s orbital

6. A bonding orbital for N2-H6 with 1.9925 electrons
__has 70.75% N 2 character in a sp2.20 hybrid
__has 29.25% H 6 character in a s orbital

10. A lone pair orbital for N2 with 1.8075 electrons
__made from a p3 hybrid

11. A lone pair orbital for O3 with 1.9829 electrons
__made from a sp0.61 hybrid

12. A lone pair orbital for O3 with 1.8890 electrons
__made from a p3 hybrid

86. A antibonding orbital for C1-O3 with 0.1842 electrons
__has 74.17% C 1 character in a p3 hybrid
__has 25.83% O 3 character in a p3 hybrid

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

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.

The interaction of lone pair donor orbital, 10, for N2 with the antibonding acceptor orbital, 86, for C1-O3 is 343. kJ/mol.

The interaction of the second lone pair donor orbital, 12, for O3 with the antibonding acceptor orbital, 85, for C1-N2 is 131. kJ/mol.

The interaction of the second lone pair donor orbital, 12, for O3 with the antibonding acceptor orbital, 88, for C1-H4 is 124. kJ/mol.

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.

16 ----- 3.086

15 ----- 1.593

14 ----- 0.908


13 ----- -1.040


12 -^-v- -6.069

11 -^-v- -6.887


10 -^-v- -10.05
9 -^-v- -10.11


8 -^-v- -11.87


7 -^-v- -13.96


6 -^-v- -15.60


5 -^-v- -22.65


4 -^-v- -25.72


3 -^-v- -269.0


2 -^-v- -378.3


1 -^-v- -505.8

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 = -169.9648693058 Hartrees

Top of page.

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