CH3CH2CH2CHO+•, butyraldehyde radical cation

H8
\
H12H11C5 - H6
\ / / \
C3 - C4H7
/ / \
O1 = C2H9H10
\
H13
The ion charge is 1. The multiplicity is 2.

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

O1 charge=-0.053
C2 charge= 0.341
C3 charge=-0.272
C4 charge= 0.038
C5 charge=-0.376
H6 charge= 0.162
H7 charge= 0.200
H8 charge= 0.166
H9 charge= 0.109
H10 charge= 0.078
H11 charge= 0.202
H12 charge= 0.202
H13 charge= 0.199
with a dipole moment of 12.46459 Debye

Bond Lengths:

between O1 and C2: distance=1.205 ang___ between C2 and C3: distance=1.563 ang___
between C2 and H9: distance=2.814 ang___ between C2 and H12: distance=2.187 ang___
between C2 and H13: distance=1.121 ang___ between C3 and C4: distance=1.541 ang___
between C3 and H9: distance=2.206 ang___ between C3 and H10: distance=2.185 ang___
between C3 and H11: distance=1.115 ang___ between C3 and H12: distance=1.103 ang___
between C3 and H13: distance=2.308 ang___ between C4 and C5: distance=1.553 ang___
between C4 and H7: distance=2.139 ang___ between C4 and H9: distance=1.105 ang___
between C4 and H10: distance=1.106 ang___ between C4 and H11: distance=2.228 ang___
between C4 and H12: distance=2.232 ang___ between C5 and H6: distance=1.101 ang___
between C5 and H7: distance=1.115 ang___ between C5 and H8: distance=1.104 ang___
between C5 and H9: distance=2.179 ang___

Bond Angles:

for C3-C2-O1: angle=120.2 deg___ for C4-C3-C2: angle=108.8 deg___
for C5-C4-C3: angle=106.0 deg___ for H6-C5-C4: angle=111.9 deg___
for H7-C5-C4: angle=105.4 deg___ for H8-C5-C4: angle=113.9 deg___
for H9-C4-C3: angle=111.8 deg___ for H10-C4-C3: angle=110.1 deg___
for H11-C3-C2: angle=101.6 deg___ for H12-C3-C2: angle=108.9 deg___
for H13-C2-O1: angle=122.1 deg___

Top of page.

Bond Orders (Mulliken):

between O1 and C2: order=1.651___ between C2 and C3: order=0.799___
between C2 and H9: order=0.060___ between C2 and H12: order=-0.106___
between C2 and H13: order=0.811___ between C3 and C4: order=0.517___
between C3 and H9: order=-0.070___ between C3 and H10: order=-0.057___
between C3 and H11: order=0.932___ between C3 and H12: order=1.026___
between C3 and H13: order=0.057___ between C4 and C5: order=0.697___
between C4 and H7: order=-0.053___ between C4 and H9: order=0.989___
between C4 and H10: order=1.019___ between C4 and H11: order=-0.062___
between C4 and H12: order=-0.057___ between C5 and H6: order=0.972___
between C5 and H7: order=0.995___ between C5 and H8: order=0.970___
between C5 and H9: order=-0.068___

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. 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 O1-C2 with 0.9900 electrons
__has 74.95% O 1 character in a s0.96 p3 hybrid
__has 25.05% C 2 character in a s0.73 p3 hybrid

2. A bonding orbital for O1-C2 with 0.9910 electrons
__has 79.15% O 1 character in a s0.50 p3 hybrid
__has 20.85% C 2 character in a s0.40 p3 hybrid

3. A bonding orbital for C2-C3 with 0.9960 electrons
__has 51.93% C 2 character in a sp1.70 hybrid
__has 48.07% C 3 character in a s0.77 p3 hybrid

4. A bonding orbital for C2-H13 with 0.9962 electrons
__has 59.25% C 2 character in a sp2.09 hybrid
__has 40.75% H13 character in a s orbital

5. A bonding orbital for C3-C4 with 0.9876 electrons
__has 54.75% C 3 character in a sp2.26 hybrid
__has 45.25% C 4 character in a s0.97 p3 hybrid

6. A bonding orbital for C3-H11 with 0.9802 electrons
__has 62.71% C 3 character in a s0.90 p3 hybrid
__has 37.29% H11 character in a s orbital

7. A bonding orbital for C3-H12 with 0.9933 electrons
__has 62.93% C 3 character in a sp2.84 hybrid
__has 37.07% H12 character in a s orbital

8. A bonding orbital for C4-C5 with 0.9927 electrons
__has 53.38% C 4 character in a sp2.55 hybrid
__has 46.62% C 5 character in a sp2.67 hybrid

9. A bonding orbital for C4-H9 with 0.9926 electrons
__has 60.54% C 4 character in a s0.93 p3 hybrid
__has 39.46% H 9 character in a s orbital

10. A bonding orbital for C4-H10 with 0.9925 electrons
__has 60.12% C 4 character in a s0.93 p3 hybrid
__has 39.88% H10 character in a s orbital

11. A bonding orbital for C5-H6 with 0.9963 electrons
__has 60.09% C 5 character in a sp2.96 hybrid
__has 39.91% H 6 character in a s orbital

12. A bonding orbital for C5-H7 with 0.9941 electrons
__has 60.74% C 5 character in a s0.88 p3 hybrid
__has 39.26% H 7 character in a s orbital

13. A bonding orbital for C5-H8 with 0.9961 electrons
__has 60.31% C 5 character in a sp2.99 hybrid
__has 39.69% H 8 character in a s orbital

19. A lone pair orbital for O1 with 0.9937 electrons
__made from a sp0.62 hybrid

20. A lone pair orbital for O1 with 0.9749 electrons
__made from a p3 hybrid

-With core pairs on: O 1 C 2 C 3 C 4 C 5 -

Up Electrons

1. A bonding orbital for O1-C2 with 0.9990 electrons
__has 64.81% O 1 character in a sp1.40 hybrid
__has 35.19% C 2 character in a sp2.25 hybrid

2. A bonding orbital for O1-C2 with 0.9986 electrons
__has 75.02% O 1 character in a p3 hybrid
__has 24.98% C 2 character in a p3 hybrid

3. A bonding orbital for C2-C3 with 0.9390 electrons
__has 60.45% C 2 character in a sp1.65 hybrid
__has 39.55% C 3 character in a s0.69 p3 hybrid

4. A bonding orbital for C2-H13 with 0.9575 electrons
__has 67.14% C 2 character in a sp2.10 hybrid
__has 32.86% H13 character in a s orbital

5. A bonding orbital for C3-C4 with 0.9831 electrons
__has 54.44% C 3 character in a sp2.18 hybrid
__has 45.56% C 4 character in a s0.98 p3 hybrid

6. A bonding orbital for C3-H11 with 0.9772 electrons
__has 62.13% C 3 character in a s0.92 p3 hybrid
__has 37.87% H11 character in a s orbital

7. A bonding orbital for C3-H12 with 0.9943 electrons
__has 62.21% C 3 character in a sp2.78 hybrid
__has 37.79% H12 character in a s orbital

8. A bonding orbital for C4-C5 with 0.9882 electrons
__has 53.65% C 4 character in a sp2.52 hybrid
__has 46.35% C 5 character in a sp2.68 hybrid

9. A bonding orbital for C4-H9 with 0.9922 electrons
__has 60.61% C 4 character in a s0.92 p3 hybrid
__has 39.39% H 9 character in a s orbital

10. A bonding orbital for C4-H10 with 0.9924 electrons
__has 60.09% C 4 character in a s0.93 p3 hybrid
__has 39.91% H10 character in a s orbital

11. A bonding orbital for C5-H6 with 0.9963 electrons
__has 60.05% C 5 character in a sp2.96 hybrid
__has 39.95% H 6 character in a s orbital

12. A bonding orbital for C5-H7 with 0.9921 electrons
__has 60.94% C 5 character in a s0.88 p3 hybrid
__has 39.06% H 7 character in a s orbital

13. A bonding orbital for C5-H8 with 0.9961 electrons
__has 60.28% C 5 character in a sp2.99 hybrid
__has 39.72% H 8 character in a s orbital

19. A lone pair orbital for O1 with 0.9931 electrons
__made from a sp0.71 hybrid

20. A lone pair orbital for O1 with 0.1102 electrons
__made from a p3 hybrid

-With core pairs on: O 1 C 2 C 3 C 4 C 5 -

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, 3, for C2-C3 with the second lone pair acceptor orbital, 20, for O1 is 87.7 kJ/mol.

The interaction of bonding donor orbital, 4, for C2-H13 with the second lone pair acceptor orbital, 20, for O1 is 68.3 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. Only the spin up electron orbital energies are given.

24 ----- -3.415

23 ----- -3.546

22 ----- -4.032


21 ----- -9.186


20 -^--- -13.35

19 -^-v- -13.67

18 -^-v- -14.11

17 -^-v- -14.83

16 -^-v- -15.11

15 -^-v- -15.92


14 -^-v- -16.94

13 -^-v- -17.79

12 -^-v- -18.08

11 -^-v- -18.92


10 -^-v- -20.33

9 -^-v- -21.13


8 -^-v- -23.44


7 -^-v- -25.99


6 -^-v- -34.47


5 -^-v- -271.4

4 -^-v- -272.4


3 -^-v- -273.5


2 -^-v- -276.2


1 -^-v- -515.4

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 = -232.1854344289 Hartrees

Top of page.

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