(HO)2NH, Dihydroxylamine

H5O3
| / |
O1 - N2H4
|
H6
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=-0.410
N2 charge=-0.507
O3 charge=-0.410
H4 charge= 0.429
H5 charge= 0.470
H6 charge= 0.429
with a dipole moment of 1.81312 Debye

Bond Lengths:

between O1 and N2: distance=1.459 ang___ between O1 and O3: distance=2.357 ang___
between O1 and H6: distance=0.977 ang___ between N2 and O3: distance=1.459 ang___
between N2 and H5: distance=1.031 ang___ between O3 and H4: distance=0.978 ang___

Bond Angles:

for O3-N2-O1: angle=107.7 deg___ for H4-O3-N2: angle=102.0 deg___
for H5-N2-O1: angle=99.86 deg___ for H6-O1-N2: angle=102.0 deg___

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Bond Orders (Mulliken):

between O1 and N2: order=0.916___ between O1 and O3: order=-0.077___
between O1 and H6: order=0.864___ between N2 and O3: order=0.915___
between N2 and H5: order=0.932___ between O3 and H4: order=0.864___

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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.

Hybridization in the Best Lewis Structure

1. A bonding orbital for O1-N2 with 1.9932 electrons
__has 57.40% O 1 character in a s0.59 p3 hybrid
__has 42.60% N 2 character in a s0.62 p3 hybrid

2. A bonding orbital for O1-H6 with 1.9954 electrons
__has 73.42% O 1 character in a s0.84 p3 hybrid
__has 26.58% H 6 character in a s orbital

3. A bonding orbital for N2-O3 with 1.9932 electrons
__has 42.61% N 2 character in a s0.62 p3 hybrid
__has 57.39% O 3 character in a s0.60 p3 hybrid

4. A bonding orbital for N2-H5 with 1.9898 electrons
__has 67.37% N 2 character in a s0.93 p3 hybrid
__has 32.63% H 5 character in a s orbital

5. A bonding orbital for O3-H4 with 1.9953 electrons
__has 73.42% O 3 character in a s0.84 p3 hybrid
__has 26.58% H 4 character in a s orbital

9. A lone pair orbital for O1 with 1.9976 electrons
__made from a sp0.64 hybrid

10. A lone pair orbital for O1 with 1.9692 electrons
__made from a p3 hybrid

11. A lone pair orbital for N2 with 1.9960 electrons
__made from a sp1.33 hybrid

12. A lone pair orbital for O3 with 1.9976 electrons
__made from a sp0.65 hybrid

13. A lone pair orbital for O3 with 1.9691 electrons
__made from a p3 hybrid

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

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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 the second lone pair donor orbital, 10, for O1 with the antibonding acceptor orbital, 88, for N2-O3 is 51.4 kJ/mol.

The interaction of the second lone pair donor orbital, 13, for O3 with the antibonding acceptor orbital, 86, for O1-N2 is 51.6 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.

17 ----- 2.259

16 ----- 0.750
15 ----- 0.692

14 ----- 0.031


13 -^-v- -6.211

12 -^-v- -7.154

11 -^-v- -7.997


10 -^-v- -9.994


9 -^-v- -11.98

8 -^-v- -12.60

7 -^-v- -13.33


6 -^-v- -19.28


5 -^-v- -25.12


4 -^-v- -27.54


3 -^-v- -380.1


2 -^-v- -507.4 1 -^-v- -507.4

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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 = -206.9936229028 Hartrees

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