Formamide anion-water complex*, HCONH-.H2O

H8
\
N3H7
/ |
O5 = C1O2
| |
H4H6
The ion charge is -1.

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= 0.590
O2 charge=-0.921
N3 charge=-0.965
H4 charge=-0.061
O5 charge=-0.746
H6 charge= 0.343
H7 charge= 0.433
H8 charge= 0.325
with a dipole moment of 1.84746 Debye

Bond Lengths:

between C1 and N3: distance=1.338 ang___ between C1 and H4: distance=1.127 ang___
between C1 and O5: distance=1.272 ang___ between O2 and H6: distance=0.973 ang___
between O2 and H7: distance=1.051 ang___ between N3 and H4: distance=2.047 ang___
between N3 and O5: distance=2.364 ang___ between N3 and H8: distance=1.033 ang___

Bond Angles:

for N3-C1-O2: angle=36.65 deg___ for H4-C1-O2: angle=75.42 deg___
for O5-C1-O2: angle=166.5 deg___ for H6-O2-C1: angle=94.82 deg___
for H7-O2-C1: angle=17.84 deg___ for H8-O2-C1: angle=31.82 deg___

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Bond Orders (Mulliken):

between C1 and N3: order=1.333___ between C1 and H4: order=1.053___
between C1 and O5: order=1.527___ between O2 and H6: order=0.920___
between O2 and H7: order=0.703___ between N3 and H4: order=-0.109___
between N3 and O5: order=-0.113___ between N3 and H8: order=0.924___

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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. 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-N3 with 1.9971 electrons
__has 41.07% C 1 character in a sp1.67 hybrid
__has 58.93% N 3 character in a sp1.72 hybrid

2. A bonding orbital for C1-N3 with 1.9965 electrons
__has 22.06% C 1 character in a p3 hybrid
__has 77.94% N 3 character in a p3 hybrid

3. A bonding orbital for C1-H4 with 1.9830 electrons
__has 53.70% C 1 character in a sp2.55 hybrid
__has 46.30% H 4 character in a s orbital

4. A bonding orbital for C1-O5 with 1.9971 electrons
__has 35.91% C 1 character in a sp1.84 hybrid
__has 64.09% O 5 character in a sp1.78 hybrid

5. A bonding orbital for O2-H6 with 1.9986 electrons
__has 71.36% O 2 character in a s0.78 p3 hybrid
__has 28.64% H 6 character in a s orbital

6. A bonding orbital for O2-H7 with 1.9976 electrons
__has 80.25% O 2 character in a sp2.35 hybrid
__has 19.75% H 7 character in a s orbital

7. A bonding orbital for N3-H8 with 1.9822 electrons
__has 66.24% N 3 character in a s0.91 p3 hybrid
__has 33.76% H 8 character in a s orbital

12. A lone pair orbital for O2 with 1.9977 electrons
__made from a s0.28 p3 hybrid

13. A lone pair orbital for O2 with 1.9974 electrons
__made from a sp1.45 hybrid

14. A lone pair orbital for N3 with 1.8861 electrons
__made from a sp1.48 hybrid

15. A lone pair orbital for O5 with 1.9810 electrons
__made from a sp0.56 hybrid

16. A lone pair orbital for O5 with 1.9108 electrons
__made from a p3 hybrid

17. A lone pair orbital for O5 with 1.6761 electrons
__made from a p3 hybrid

115. A antibonding orbital for C1-N3 with 0.3098 electrons
__has 77.94% C 1 character in a p3 hybrid
__has 22.06% N 3 character in a p3 hybrid

-With core pairs on: C 1 O 2 N 3 O 5 -

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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, 3, for C1-H4 with the antibonding acceptor orbital, 120, for N3-H8 is 24.6 kJ/mol.

The interaction of bonding donor orbital, 7, for N3-H8 with the antibonding acceptor orbital, 116, for C1-H4 is 30.8 kJ/mol.

The interaction of lone pair donor orbital, 14, for N3 with the antibonding acceptor orbital, 117, for C1-O5 is 64.3 kJ/mol.

The interaction of the second lone pair donor orbital, 16, for O5 with the antibonding acceptor orbital, 114, for C1-N3 is 89.9 kJ/mol.

The interaction of the second lone pair donor orbital, 16, for O5 with the antibonding acceptor orbital, 116, for C1-H4 is 117. kJ/mol.

The interaction of the third lone pair donor orbital, 17, for O5 with the second antibonding acceptor orbital, 115, for C1-N3 is 660. kJ/mol.

The interaction of bonding donor orbital, 1, for C1-N3 with the antibonding acceptor orbital, 119, for O2-H7 is 2.92 kJ/mol.

The interaction of lone pair donor orbital, 14, for N3 with the antibonding acceptor orbital, 119, for O2-H7 is 238. 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.

21 ----- 7.999

20 ----- 6.654

19 ----- 5.829

18 ----- 5.014


17 -^-v- -0.143

16 -^-v- -0.380


15 -^-v- -1.499

14 -^-v- -1.680


13 -^-v- -3.833
12 -^-v- -3.929


11 -^-v- -4.989

10 -^-v- -5.430


9 -^-v- -7.169


8 -^-v- -8.845


7 -^-v- -15.46


6 -^-v- -18.90

5 -^-v- -19.25


4 -^-v- -262.8


3 -^-v- -371.0


2 -^-v- -499.8

1 -^-v- -500.5

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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 = -245.8725828710 Hartrees

* For an interesting discussion of this ion see C&ENews, 1996, Sept. 30, p 37.

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