tert-butyl cation, (CH3)3C+

H12
/
H11 - C10 - H13H3
\ /
H9C1 - C2
\ / | \
H7 - C6H5H4
\
H8
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= 0.588
C2 charge=-0.554
H3 charge= 0.208
H4 charge= 0.241
H5 charge= 0.239
C6 charge=-0.542
H7 charge= 0.240
H8 charge= 0.205
H9 charge= 0.236
C10 charge=-0.551
H11 charge= 0.207
H12 charge= 0.241
H13 charge= 0.239
with a dipole moment of 0.12793 Debye

Bond Lengths:

between C1 and C2: distance=1.466 ang___ between C1 and H3: distance=2.174 ang___
between C1 and C6: distance=1.465 ang___ between C1 and H8: distance=2.173 ang___
between C1 and C10: distance=1.466 ang___ between C1 and H11: distance=2.175 ang___
between C2 and H3: distance=1.099 ang___ between C2 and H4: distance=1.115 ang___
between C2 and H5: distance=1.114 ang___ between C2 and C6: distance=2.538 ang___
between C2 and C10: distance=2.539 ang___ between C6 and H7: distance=1.116 ang___
between C6 and H8: distance=1.099 ang___ between C6 and H9: distance=1.111 ang___
between C6 and C10: distance=2.538 ang___ between C10 and H11: distance=1.100 ang___
between C10 and H12: distance=1.116 ang___ between C10 and H13: distance=1.112 ang___

Bond Angles:

for H3-C2-C1: angle=115.0 deg___ for H4-C2-C1: angle=108.4 deg___
for H5-C2-C1: angle=109.3 deg___ for C6-C1-C2: angle=119.9 deg___
for H7-C6-C1: angle=107.6 deg___ for H8-C6-C1: angle=115.1 deg___
for H9-C6-C1: angle=110.0 deg___ for C10-C1-C2: angle=119.9 deg___
for H11-C10-C1: angle=115.2 deg___ for H12-C10-C1: angle=107.7 deg___
for H13-C10-C1: angle=109.8 deg___

Top of page.

Bond Orders (Mulliken):

between C1 and C2: order=0.771___ between C1 and H3: order=-0.077___
between C1 and C6: order=0.773___ between C1 and H8: order=-0.076___
between C1 and C10: order=0.772___ between C1 and H11: order=-0.077___
between C2 and H3: order=0.987___ between C2 and H4: order=0.912___
between C2 and H5: order=0.923___ between C2 and C6: order=0.070___
between C2 and C10: order=0.072___ between C6 and H7: order=0.901___
between C6 and H8: order=0.986___ between C6 and H9: order=0.934___
between C6 and C10: order=0.075___ between C10 and H11: order=0.987___
between C10 and H12: order=0.904___ between C10 and H13: order=0.930___

Top of page.

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 -

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, 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.

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.

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

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 = -157.5923576036 Hartrees

* Note: The symmetrical tert-butyl cation, Cs has a higher energy than this unsymmetrical conformer.

Top of page.

-> Return to Molecular Structure Page. -> Return to Chemistry Home Page