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-C2 with 1.9859 electrons
__has 49.43% C 1 character in a sp1.99 hybrid
__has 50.57% C 2 character in a sp2.26 hybrid
2. A bonding orbital for C1-C6 with 1.9859 electrons
__has 49.41% C 1 character in a sp1.99 hybrid
__has 50.59% C 6 character in a sp2.26 hybrid
3. A bonding orbital for C1-C10 with 1.9859 electrons
__has 49.42% C 1 character in a sp1.99 hybrid
__has 50.58% C10 character in a sp2.26 hybrid
4. A bonding orbital for C2-H3 with 1.9889 electrons
__has 62.30% C 2 character in a sp2.88 hybrid
__has 37.70% H 3 character in a s orbital
5. A bonding orbital for C2-H4 with 1.9407 electrons
__has 63.29% C 2 character in a s0.83 p3 hybrid
__has 36.71% H 4 character in a s orbital
6. A bonding orbital for C2-H5 with 1.9455 electrons
__has 63.26% C 2 character in a s0.85 p3 hybrid
__has 36.74% H 5 character in a s orbital
7. A bonding orbital for C6-H7 with 1.9354 electrons
__has 63.33% C 6 character in a s0.81 p3 hybrid
__has 36.67% H 7 character in a s orbital
8. A bonding orbital for C6-H8 with 1.9885 electrons
__has 62.32% C 6 character in a sp2.88 hybrid
__has 37.68% H 8 character in a s orbital
9. A bonding orbital for C6-H9 with 1.9501 electrons
__has 63.20% C 6 character in a s0.87 p3 hybrid
__has 36.80% H 9 character in a s orbital
10. A bonding orbital for C10-H11 with 1.9886 electrons
__has 62.34% C10 character in a sp2.87 hybrid
__has 37.66% H11 character in a s orbital
11. A bonding orbital for C10-H12 with 1.9362 electrons
__has 63.34% C10 character in a s0.81 p3 hybrid
__has 36.66% H12 character in a s orbital
12. A bonding orbital for C10-H13 with 1.9491 electrons
__has 63.20% C10 character in a s0.86 p3 hybrid
__has 36.80% H13 character in a s orbital
17. A lone pair orbital for C1 with 0.2943 electrons
__made from a p-pi orbital (100.00% p)
-With core pairs on: C 1 C 2 C 6 C10 -
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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 antibonding acceptor orbital, 140, for C1-C6 is 27.7 kJ/mol.
The interaction of bonding donor orbital, 5, for C2-H4 with
the lone pair acceptor orbital, 17, for C1 is 76.1 kJ/mol.
The interaction of bonding donor orbital, 6, for C2-H5 with
the lone pair acceptor orbital, 17, for C1 is 66.1 kJ/mol.
The interaction of bonding donor orbital, 7, for C6-H7 with
the lone pair acceptor orbital, 17, for C1 is 86.3 kJ/mol.
The interaction of bonding donor orbital, 8, for C6-H8 with
the antibonding acceptor orbital, 141, for C1-C10 is 27.6 kJ/mol.
The interaction of bonding donor orbital, 9, for C6-H9 with
the lone pair acceptor orbital, 17, for C1 is 57.1 kJ/mol.
The interaction of bonding donor orbital, 10, for C10-H11 with
the antibonding acceptor orbital, 139, for C1-C2 is 27.6 kJ/mol.
The interaction of bonding donor orbital, 11, for C10-H12 with
the lone pair acceptor orbital, 17, for C1 is 84.1 kJ/mol.
The interaction of bonding donor orbital, 12, for C10-H13 with
the lone pair acceptor orbital, 17, for C1 is 59.2 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.
20 ----- -2.633 19 ----- -2.637
18 ----- -3.819
17 ----- -9.654
16 -^-v- -14.72 15 -^-v- -14.72
14 -^-v- -14.79
13 -^-v- -15.15 12 -^-v- -15.15
11 -^-v- -17.07
10 -^-v- -17.14 9 -^-v- -17.14
8 -^-v- -19.07
7 -^-v- -23.22 6 -^-v- -23.23
5 -^-v- -26.70
4 -^-v- -272.1 3 -^-v- -272.1 2 -^-v- -272.1
1 -^-v- -274.9
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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 = -157.5923576036 Hartrees
* Note: The symmetrical tert-butyl cation, Cs
has a higher energy than this unsymmetrical conformer.
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