HCNO (see note*)

 H3 / C2 /// N1 / O4
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

N1 charge= 0.476
C2 charge=-0.463
H3 charge= 0.333
O4 charge=-0.346
with a dipole moment of 2.99514 Debye

Bond Lengths:

between N1 and C2: distance=1.175 ang___ between N1 and O4: distance=1.213 ang___
between C2 and H3: distance=1.071 ang___ between C2 and O4: distance=2.388 ang___

Bond Angles:

for H3-N1-C2: angle=0.109 deg___ for O4-N1-C2: angle=179.9 deg___

Bond Orders (Mulliken):

between N1 and C2: order=2.406___ between N1 and O4: order=1.077___
between C2 and H3: order=0.900___ between C2 and O4: order=0.333___

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 N1-C2 with 1.9943 electrons
__has 62.86% N 1 character in a sp0.75 hybrid
__has 37.14% C 2 character in a sp1.28 hybrid

2. A bonding orbital for N1-C2 with 1.9947 electrons
__has 56.65% N 1 character in a p-pi orbital ( 99.78% p 0.22% d)
__has 43.35% C 2 character in a p-pi orbital ( 99.73% p 0.27% d)

3. A bonding orbital for N1-C2 with 1.9947 electrons
__has 56.65% N 1 character in a p-pi orbital ( 99.78% p 0.22% d)
__has 43.35% C 2 character in a p-pi orbital ( 99.73% p 0.27% d)

4. A bonding orbital for N1-O4 with 1.9967 electrons
__has 52.47% N 1 character in a sp1.32 hybrid
__has 47.53% O 4 character in a s0.90 p3 hybrid

5. A bonding orbital for C2-H3 with 1.9883 electrons
__has 63.32% C 2 character in a sp0.78 hybrid
__has 36.68% H 3 character in a s orbital

9. A lone pair orbital for O4 with 1.9821 electrons

10. A lone pair orbital for O4 with 1.7725 electrons
__made from a p-pi orbital ( 99.89% p 0.11% d)

11. A lone pair orbital for O4 with 1.7725 electrons
__made from a p-pi orbital ( 99.89% p 0.11% d)

75. A antibonding orbital for N1-C2 with 0.2190 electrons
__has 43.35% N 1 character in a p-pi orbital ( 99.78% p 0.22% d)
__has 56.65% C 2 character in a p-pi orbital ( 99.73% p 0.27% d)

76. A antibonding orbital for N1-C2 with 0.2190 electrons
__has 43.35% N 1 character in a p-pi orbital ( 99.78% p 0.22% d)
__has 56.65% C 2 character in a p-pi orbital ( 99.73% p 0.27% d)

-With core pairs on: N 1 C 2 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, 4, for N1-O4 with the antibonding acceptor orbital, 74, for N1-C2 is 22.5 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-H3 with the antibonding acceptor orbital, 74, for N1-C2 is 21.7 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-H3 with the antibonding acceptor orbital, 77, for N1-O4 is 34.2 kJ/mol.

The interaction of lone pair donor orbital, 9, for O4 with the antibonding acceptor orbital, 74, for N1-C2 is 83.3 kJ/mol.

The interaction of the second lone pair donor orbital, 10, for O4 with the third antibonding acceptor orbital, 76, for N1-C2 is 431. kJ/mol.

The interaction of the third lone pair donor orbital, 11, for O4 with the second antibonding acceptor orbital, 75, for N1-C2 is 431. 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.

15 ----- 2.270

14 ----- 0.848

13 ----- -1.177 12 ----- -1.177

11 -^-v- -6.887 10 -^-v- -6.887

9 -^-v- -12.29 8 -^-v- -12.29

7 -^-v- -13.17

6 -^-v- -14.79

5 -^-v- -22.93

4 -^-v- -29.28

3 -^-v- -268.2

2 -^-v- -381.5

1 -^-v- -507.9

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 = -168.6510480050 Hartrees