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 O1-C2 with 1.9946 electrons
__has 63.69% O 1 character in a sp1.67 hybrid
__has 36.31% C 2 character in a sp1.96 hybrid
2. A bonding orbital for O1-C2 with 1.9919 electrons
__has 74.85% O 1 character in a p3 hybrid
__has 25.15% C 2 character in a p3 hybrid
3. A bonding orbital for C2-N3 with 1.9942 electrons
__has 37.41% C 2 character in a sp2.20 hybrid
__has 62.59% N 3 character in a sp1.76 hybrid
4. A bonding orbital for C2-C9 with 1.9901 electrons
__has 48.86% C 2 character in a sp1.88 hybrid
__has 51.14% C 9 character in a sp2.76 hybrid
5. A bonding orbital for N3-C4 with 1.9934 electrons
__has 62.11% N 3 character in a sp1.84 hybrid
__has 37.89% C 4 character in a sp2.92 hybrid
6. A bonding orbital for N3-H8 with 1.9859 electrons
__has 70.56% N 3 character in a sp2.61 hybrid
__has 29.44% H 8 character in a s orbital
7. A bonding orbital for C4-H5 with 1.9945 electrons
__has 58.76% C 4 character in a sp2.96 hybrid
__has 41.24% H 5 character in a s orbital
8. A bonding orbital for C4-H6 with 1.9919 electrons
__has 59.46% C 4 character in a s0.98 p3 hybrid
__has 40.54% H 6 character in a s orbital
9. A bonding orbital for C4-H7 with 1.9924 electrons
__has 59.12% C 4 character in a s0.99 p3 hybrid
__has 40.88% H 7 character in a s orbital
10. A bonding orbital for C9-H10 with 1.9918 electrons
__has 61.22% C 9 character in a sp2.98 hybrid
__has 38.78% H10 character in a s orbital
11. A bonding orbital for C9-H11 with 1.9836 electrons
__has 60.03% C 9 character in a s0.96 p3 hybrid
__has 39.97% H11 character in a s orbital
12. A bonding orbital for C9-H12 with 1.9827 electrons
__has 60.11% C 9 character in a s0.96 p3 hybrid
__has 39.89% H12 character in a s orbital
18. A lone pair orbital for O1 with 1.9778 electrons
__made from a sp0.61 hybrid
19. A lone pair orbital for O1 with 1.9014 electrons
__made from a p3 hybrid
20. A lone pair orbital for N3 with 1.7842 electrons
__made from a p3 hybrid
152. A antibonding orbital for O1-C2 with 0.2048 electrons
__has 25.15% O 1 character in a p3 hybrid
__has 74.85% C 2 character in a p3 hybrid
-With core pairs on: O 1 C 2 N 3 C 4 C 9 -
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 bonding donor orbital, 6, for N3-H8 with
the antibonding acceptor orbital, 154, for C2-C9 is 23.0 kJ/mol.
The interaction of bonding donor orbital, 10, for C9-H10 with
the antibonding acceptor orbital, 153, for C2-N3 is 21.4 kJ/mol.
The interaction of bonding donor orbital, 11, for C9-H11 with
the second antibonding acceptor orbital, 152, for O1-C2 is 26.4 kJ/mol.
The interaction of the second lone pair donor orbital, 19, for O1 with
the antibonding acceptor orbital, 153, for C2-N3 is 129. kJ/mol.
The interaction of the second lone pair donor orbital, 19, for O1 with
the antibonding acceptor orbital, 154, for C2-C9 is 107. kJ/mol.
The interaction of lone pair donor orbital, 20, for N3 with
the second antibonding acceptor orbital, 152, for O1-C2 is 336. kJ/mol.
The interaction of lone pair donor orbital, 20, for N3 with
the antibonding acceptor orbital, 157, for C4-H5 is 46.5 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.
24 ----- 1.565
23 ----- 1.266
22 ----- 0.929
21 ----- -0.660
20 -^-v- -5.685
19 -^-v- -6.093
18 -^-v- -8.757
17 -^-v- -9.481
16 -^-v- -9.721
15 -^-v- -9.940
14 -^-v- -10.37
13 -^-v- -11.48
12 -^-v- -11.65
11 -^-v- -12.36
10 -^-v- -14.35
9 -^-v- -17.51
8 -^-v- -18.22
7 -^-v- -22.77
6 -^-v- -25.41
5 -^-v- -266.4
4 -^-v- -267.5
3 -^-v- -268.9
2 -^-v- -378.1
1 -^-v- -505.3
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 = -248.6108328618 Hartrees
Top of page.
-> Return to Molecular Structure Page.
-> Return to Chemistry Home Page