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.
The Lewis structure is built for the up and down electrons,
separately. Note that the up and down structures can be very
different.
Hybridization in the Best Lewis Structure
Down Electrons
1. A bonding orbital for C1-C2 with 0.9977 electrons
__has 53.84% C 1 character in a sp2.00 hybrid
__has 46.16% C 2 character in a sp2.42 hybrid
2. A bonding orbital for C1-C6 with 0.9977 electrons
__has 53.81% C 1 character in a sp2.00 hybrid
__has 46.19% C 6 character in a sp2.41 hybrid
3. A bonding orbital for C1-H10 with 0.9921 electrons
__has 61.12% C 1 character in a s0.59 p3 hybrid
__has 38.88% H10 character in a s orbital
4. A bonding orbital for C1-H11 with 0.9918 electrons
__has 61.31% C 1 character in a s0.62 p3 hybrid
__has 38.69% H11 character in a s orbital
5. A bonding orbital for C2-H3 with 0.9933 electrons
__has 61.17% C 2 character in a s0.83 p3 hybrid
__has 38.83% H 3 character in a s orbital
6. A bonding orbital for C2-H4 with 0.9951 electrons
__has 62.17% C 2 character in a sp2.91 hybrid
__has 37.83% H 4 character in a s orbital
7. A bonding orbital for C2-H5 with 0.9940 electrons
__has 61.81% C 2 character in a s0.93 p3 hybrid
__has 38.19% H 5 character in a s orbital
8. A bonding orbital for C6-H7 with 0.9933 electrons
__has 61.22% C 6 character in a s0.84 p3 hybrid
__has 38.78% H 7 character in a s orbital
9. A bonding orbital for C6-H8 with 0.9938 electrons
__has 61.72% C 6 character in a s0.91 p3 hybrid
__has 38.28% H 8 character in a s orbital
10. A bonding orbital for C6-H9 with 0.9952 electrons
__has 62.19% C 6 character in a sp2.89 hybrid
__has 37.81% H 9 character in a s orbital
-With core pairs on: C 1 C 2 C 6 -
Up Electrons
1. A bonding orbital for C1-C2 with 0.9976 electrons
__has 52.18% C 1 character in a sp1.95 hybrid
__has 47.82% C 2 character in a sp2.36 hybrid
2. A bonding orbital for C1-C6 with 0.9976 electrons
__has 52.16% C 1 character in a sp1.94 hybrid
__has 47.84% C 6 character in a sp2.36 hybrid
3. A bonding orbital for C1-H11 with 0.8466 electrons
__has 78.43% C 1 character in a sp2.08 hybrid
__has 21.57% H11 character in a s orbital
4. A bonding orbital for C2-H3 with 0.9333 electrons
__has 65.47% C 2 character in a s0.83 p3 hybrid
__has 34.53% H 3 character in a s orbital
5. A bonding orbital for C2-H4 with 0.9928 electrons
__has 62.31% C 2 character in a sp2.91 hybrid
__has 37.69% H 4 character in a s orbital
6. A bonding orbital for C2-H5 with 0.9629 electrons
__has 64.23% C 2 character in a s0.90 p3 hybrid
__has 35.77% H 5 character in a s orbital
7. A bonding orbital for C6-H7 with 0.9353 electrons
__has 65.44% C 6 character in a s0.84 p3 hybrid
__has 34.56% H 7 character in a s orbital
8. A bonding orbital for C6-H8 with 0.9585 electrons
__has 64.45% C 6 character in a s0.88 p3 hybrid
__has 35.55% H 8 character in a s orbital
9. A bonding orbital for C6-H9 with 0.9941 electrons
__has 62.27% C 6 character in a sp2.89 hybrid
__has 37.73% H 9 character in a s orbital
13. A lone pair orbital for C1 with 0.1771 electrons
__made from a p3 hybrid
14. A lone pair orbital for H10 with 0.1658 electrons
__made from a s orbital
-With core pairs on: C 1 C 2 C 6 -
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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, 4, for C2-H3 with
the lone pair acceptor orbital, 13, for C1 is 59.7 kJ/mol.
The interaction of bonding donor orbital, 6, for C2-H5 with
the lone pair acceptor orbital, 13, for C1 is 26.9 kJ/mol.
The interaction of bonding donor orbital, 7, for C6-H7 with
the lone pair acceptor orbital, 13, for C1 is 57.2 kJ/mol.
The interaction of bonding donor orbital, 8, for C6-H8 with
the lone pair acceptor orbital, 13, for C1 is 30.8 kJ/mol.
The interaction of lone pair donor orbital, 13, for C1 with
the antibonding acceptor orbital, 114, for C1-H11 is 41.7 kJ/mol.
The interaction of bonding donor orbital, 1, for C1-C2 with
the lone pair acceptor orbital, 14, for H10 is 14.7 kJ/mol.
The interaction of bonding donor orbital, 2, for C1-C6 with
the lone pair acceptor orbital, 14, for H10 is 15.1 kJ/mol.
The interaction of bonding donor orbital, 3, for C1-H11 with
the lone pair acceptor orbital, 14, for H10 is 531. kJ/mol.
The interaction of lone pair donor orbital, 13, for C1 with
the lone pair acceptor orbital, 14, for H10 is 423. kJ/mol.
The interaction of lone pair donor orbital, 14, for H10 with
the antibonding acceptor orbital, 114, for C1-H11 is 24.2 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.
Only the spin up electron orbital energies are given.
17 ----- -3.278
16 ----- -3.406
15 ----- -4.101
14 ----- -4.488
13 -^--- -13.90
12 -^-v- -15.04
11 -^-v- -15.18
10 -^-v- -15.37
9 -^-v- -16.84
8 -^-v- -17.63
7 -^-v- -17.71
6 -^-v- -21.50
5 -^-v- -23.39
4 -^-v- -26.53
3 -^-v- -272.5 2 -^-v- -272.5
1 -^-v- -274.1
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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 = -118.7838578579 Hartrees
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