(CH3)2C(+)CH2CH3, isopentyl cation, 2-methylbutane-2-cation

H4H5
\ |
H11H15H10C3 - H6
\ / /
C9 - C1 - C2
/ / | \
H12C13 - H16H8H7
|
H14
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= 0.492
C2 charge=-0.239
C3 charge=-0.284
H4 charge= 0.133
H5 charge= 0.129
H6 charge= 0.178
H7 charge= 0.165
H8 charge= 0.143
C9 charge=-0.601
H10 charge= 0.231
H11 charge= 0.251
H12 charge= 0.249
C13 charge=-0.491
H14 charge= 0.221
H15 charge= 0.200
H16 charge= 0.219
with a dipole moment of 1.14335 Debye

Bond Lengths:

between C1 and C2: distance=1.465 ang___ between C1 and C9: distance=1.467 ang___
between C1 and H10: distance=2.171 ang___ between C1 and C13: distance=1.468 ang___
between C1 and H15: distance=2.179 ang___ between C2 and C3: distance=1.593 ang___
between C2 and H7: distance=1.106 ang___ between C2 and H8: distance=1.103 ang___
between C2 and C9: distance=2.543 ang___ between C2 and C13: distance=2.536 ang___
between C3 and H4: distance=1.101 ang___ between C3 and H5: distance=1.101 ang___
between C3 and H6: distance=1.102 ang___ between C9 and H10: distance=1.100 ang___
between C9 and H11: distance=1.112 ang___ between C9 and H12: distance=1.114 ang___
between C9 and C13: distance=2.541 ang___ between C13 and H14: distance=1.118 ang___
between C13 and H15: distance=1.101 ang___ between C13 and H16: distance=1.108 ang___

Bond Angles:

for C3-C2-C1: angle=106.3 deg___ for H4-C3-C2: angle=111.5 deg___
for H5-C3-C2: angle=111.9 deg___ for H6-C3-C2: angle=105.9 deg___
for H7-C2-C1: angle=110.9 deg___ for H8-C2-C1: angle=112.4 deg___
for C9-C1-C2: angle=120.2 deg___ for H10-C9-C1: angle=114.8 deg___
for H11-C9-C1: angle=109.7 deg___ for H12-C9-C1: angle=108.5 deg___
for C13-C1-C2: angle=119.7 deg___ for H14-C13-C1: angle=105.8 deg___
for H15-C13-C1: angle=115.3 deg___ for H16-C13-C1: angle=111.7 deg___

Top of page.

Bond Orders (Mulliken):

between C1 and C2: order=0.884___ between C1 and C9: order=0.781___
between C1 and H10: order=-0.078___ between C1 and C13: order=0.825___
between C1 and H15: order=-0.064___ between C2 and C3: order=0.721___
between C2 and H7: order=0.949___ between C2 and H8: order=0.965___
between C2 and C9: order=0.114___ between C2 and C13: order=0.064___
between C3 and H4: order=0.962___ between C3 and H5: order=0.971___
between C3 and H6: order=0.970___ between C9 and H10: order=0.998___
between C9 and H11: order=0.911___ between C9 and H12: order=0.912___
between C9 and C13: order=0.066___ between C13 and H14: order=0.882___
between C13 and H15: order=0.981___ between C13 and H16: order=0.953___

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 1.9825 electrons
__has 49.14% C 1 character in a sp1.97 hybrid
__has 50.86% C 2 character in a sp2.40 hybrid

2. A bonding orbital for C1-C9 with 1.9850 electrons
__has 48.95% C 1 character in a sp2.01 hybrid
__has 51.05% C 9 character in a sp2.21 hybrid

3. A bonding orbital for C1-C13 with 1.9850 electrons
__has 48.92% C 1 character in a sp2.01 hybrid
__has 51.08% C13 character in a sp2.21 hybrid

4. A bonding orbital for C2-C3 with 1.9244 electrons
__has 54.94% C 2 character in a s0.96 p3 hybrid
__has 45.06% C 3 character in a sp2.96 hybrid

5. A bonding orbital for C2-H7 with 1.9647 electrons
__has 62.14% C 2 character in a s0.88 p3 hybrid
__has 37.86% H 7 character in a s orbital

6. A bonding orbital for C2-H8 with 1.9764 electrons
__has 61.80% C 2 character in a s0.93 p3 hybrid
__has 38.20% H 8 character in a s orbital

7. A bonding orbital for C3-H4 with 1.9933 electrons
__has 60.31% C 3 character in a sp2.94 hybrid
__has 39.69% H 4 character in a s orbital

8. A bonding orbital for C3-H5 with 1.9931 electrons
__has 60.42% C 3 character in a sp2.93 hybrid
__has 39.58% H 5 character in a s orbital

9. A bonding orbital for C3-H6 with 1.9825 electrons
__has 61.78% C 3 character in a s0.95 p3 hybrid
__has 38.22% H 6 character in a s orbital

10. A bonding orbital for C9-H10 with 1.9881 electrons
__has 62.19% C 9 character in a sp2.91 hybrid
__has 37.81% H10 character in a s orbital

11. A bonding orbital for C9-H11 with 1.9471 electrons
__has 63.08% C 9 character in a s0.84 p3 hybrid
__has 36.92% H11 character in a s orbital

12. A bonding orbital for C9-H12 with 1.9410 electrons
__has 63.22% C 9 character in a s0.82 p3 hybrid
__has 36.78% H12 character in a s orbital

13. A bonding orbital for C13-H14 with 1.9262 electrons
__has 63.24% C13 character in a s0.77 p3 hybrid
__has 36.76% H14 character in a s orbital

14. A bonding orbital for C13-H15 with 1.9863 electrons
__has 62.28% C13 character in a sp2.94 hybrid
__has 37.72% H15 character in a s orbital

15. A bonding orbital for C13-H16 with 1.9628 electrons
__has 62.79% C13 character in a s0.90 p3 hybrid
__has 37.21% H16 character in a s orbital

21. A lone pair orbital for C1 with 0.2954 electrons
__made from a p3 hybrid

-With core pairs on: C 1 C 2 C 3 C 9 C13 -

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-C3 with the lone pair acceptor orbital, 21, for C1 is 105. kJ/mol.

The interaction of bonding donor orbital, 5, for C2-H7 with the lone pair acceptor orbital, 21, for C1 is 23.8 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-H7 with the antibonding acceptor orbital, 174, for C1-C13 is 24.9 kJ/mol.

The interaction of bonding donor orbital, 6, for C2-H8 with the antibonding acceptor orbital, 173, for C1-C9 is 28.9 kJ/mol.

The interaction of bonding donor orbital, 10, for C9-H10 with the antibonding acceptor orbital, 174, for C1-C13 is 30.0 kJ/mol.

The interaction of bonding donor orbital, 11, for C9-H11 with the lone pair acceptor orbital, 21, for C1 is 64.0 kJ/mol.

The interaction of bonding donor orbital, 12, for C9-H12 with the lone pair acceptor orbital, 21, for C1 is 77.1 kJ/mol.

The interaction of bonding donor orbital, 13, for C13-H14 with the lone pair acceptor orbital, 21, for C1 is 109. kJ/mol.

The interaction of bonding donor orbital, 14, for C13-H15 with the antibonding acceptor orbital, 172, for C1-C2 is 26.6 kJ/mol.

The interaction of bonding donor orbital, 15, for C13-H16 with the lone pair acceptor orbital, 21, for C1 is 35.4 kJ/mol.

The interaction of bonding donor orbital, 15, for C13-H16 with the antibonding acceptor orbital, 173, for C1-C9 is 23.3 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 ----- -2.658

23 ----- -3.028

22 ----- -3.711


21 ----- -9.380


20 -^-v- -13.45

19 -^-v- -13.66

18 -^-v- -14.25

17 -^-v- -14.56

16 -^-v- -14.89
15 -^-v- -14.93

14 -^-v- -15.20


13 -^-v- -16.51

12 -^-v- -17.04
11 -^-v- -17.11


10 -^-v- -18.65


9 -^-v- -20.86


8 -^-v- -23.01

7 -^-v- -23.68


6 -^-v- -26.54


5 -^-v- -271.3

4 -^-v- -271.8 3 -^-v- -271.9

2 -^-v- -272.0


1 -^-v- -274.6

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 = -196.9184380995 Hartrees

Top of page.

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