1-dehydrobutyraldehyde cation, propyl acylium ion, CH3CH2CH2CO+

O5
||
H11C4
\ |
H6C3 - H12
\ /
H7 - C1 - C2 - H10
/ \
H8H9
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=-0.414
C2 charge= 0.091
C3 charge=-0.365
C4 charge= 0.572
O5 charge=-0.022
H6 charge= 0.136
H7 charge= 0.146
H8 charge= 0.173
H9 charge= 0.110
H10 charge= 0.082
H11 charge= 0.248
H12 charge= 0.241
with a dipole moment of 10.91911 Debye

Bond Lengths:

between C1 and C2: distance=1.530 ang___ between C1 and C3: distance=2.607 ang___
between C1 and H6: distance=1.106 ang___ between C1 and H7: distance=1.104 ang___
between C1 and H8: distance=1.103 ang___ between C1 and H10: distance=2.201 ang___
between C2 and C3: distance=1.592 ang___ between C2 and C4: distance=2.493 ang___
between C2 and H6: distance=2.210 ang___ between C2 and H9: distance=1.105 ang___
between C2 and H10: distance=1.104 ang___ between C3 and C4: distance=1.417 ang___
between C3 and O5: distance=2.555 ang___ between C3 and H11: distance=1.113 ang___
between C3 and H12: distance=1.114 ang___ between C4 and O5: distance=1.139 ang___

Bond Angles:

for C3-C2-C1: angle=113.2 deg___ for C4-C3-C2: angle=111.8 deg___
for O5-C4-C3: angle=176.8 deg___ for H6-C1-C2: angle=112.9 deg___
for H7-C1-C2: angle=111.9 deg___ for H8-C1-C2: angle=108.9 deg___
for H9-C2-C1: angle=111.5 deg___ for H10-C2-C1: angle=112.3 deg___
for H11-C3-C2: angle=111.3 deg___ for H12-C3-C2: angle=111.9 deg___

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Bond Orders (Mulliken):

between C1 and C2: order=0.788___ between C1 and C3: order=-0.101___
between C1 and H6: order=1.007___ between C1 and H7: order=0.941___
between C1 and H8: order=0.963___ between C1 and H10: order=-0.060___
between C2 and C3: order=0.954___ between C2 and C4: order=-0.090___
between C2 and H6: order=-0.053___ between C2 and H9: order=0.930___
between C2 and H10: order=0.960___ between C3 and C4: order=0.754___
between C3 and O5: order=-0.064___ between C3 and H11: order=0.916___
between C3 and H12: order=0.903___ between C4 and O5: order=2.334___

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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 1.9937 electrons
__has 47.07% C 1 character in a sp2.58 hybrid
__has 52.93% C 2 character in a sp2.24 hybrid

2. A bonding orbital for C1-H6 with 1.9907 electrons
__has 59.66% C 1 character in a s0.94 p3 hybrid
__has 40.34% H 6 character in a s orbital

3. A bonding orbital for C1-H7 with 1.9912 electrons
__has 60.31% C 1 character in a s0.96 p3 hybrid
__has 39.69% H 7 character in a s orbital

4. A bonding orbital for C1-H8 with 1.9848 electrons
__has 61.65% C 1 character in a s0.94 p3 hybrid
__has 38.35% H 8 character in a s orbital

5. A bonding orbital for C2-C3 with 1.9441 electrons
__has 41.82% C 2 character in a s0.86 p3 hybrid
__has 58.18% C 3 character in a sp2.35 hybrid

6. A bonding orbital for C2-H9 with 1.9764 electrons
__has 61.60% C 2 character in a s0.90 p3 hybrid
__has 38.40% H 9 character in a s orbital

7. A bonding orbital for C2-H10 with 1.9863 electrons
__has 60.78% C 2 character in a s0.94 p3 hybrid
__has 39.22% H10 character in a s orbital

8. A bonding orbital for C3-C4 with 1.9946 electrons
__has 46.76% C 3 character in a s0.86 p3 hybrid
__has 53.24% C 4 character in a sp0.68 hybrid

9. A bonding orbital for C3-H11 with 1.9466 electrons
__has 65.07% C 3 character in a s0.95 p3 hybrid
__has 34.93% H11 character in a s orbital

10. A bonding orbital for C3-H12 with 1.9426 electrons
__has 65.07% C 3 character in a s0.94 p3 hybrid
__has 34.93% H12 character in a s orbital

11. A bonding orbital for C4-O5 with 1.9993 electrons
__has 33.43% C 4 character in a sp1.42 hybrid
__has 66.57% O 5 character in a sp1.29 hybrid

12. A bonding orbital for C4-O5 with 1.9965 electrons
__has 25.62% C 4 character in a p3 hybrid
__has 74.38% O 5 character in a p3 hybrid

13. A bonding orbital for C4-O5 with 1.9960 electrons
__has 25.75% C 4 character in a p-pi orbital ( 99.37% p 0.63% d)
__has 74.25% O 5 character in a p3 hybrid

19. A lone pair orbital for O5 with 1.9779 electrons
__made from a sp0.76 hybrid

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

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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 C1-H8 with the antibonding acceptor orbital, 154, for C2-C3 is 25.3 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-C3 with the antibonding acceptor orbital, 160, for C4-O5 is 23.4 kJ/mol.

The interaction of bonding donor orbital, 5, for C2-C3 with the second antibonding acceptor orbital, 161, for C4-O5 is 56.4 kJ/mol.

The interaction of bonding donor orbital, 9, for C3-H11 with the antibonding acceptor orbital, 160, for C4-O5 is 20.7 kJ/mol.

The interaction of bonding donor orbital, 9, for C3-H11 with the third antibonding acceptor orbital, 162, for C4-O5 is 54.1 kJ/mol.

The interaction of bonding donor orbital, 10, for C3-H12 with the second antibonding acceptor orbital, 161, for C4-O5 is 22.8 kJ/mol.

The interaction of bonding donor orbital, 10, for C3-H12 with the third antibonding acceptor orbital, 162, for C4-O5 is 54.2 kJ/mol.

The interaction of lone pair donor orbital, 19, for O5 with the antibonding acceptor orbital, 157, for C3-C4 is 33.3 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.

23 ----- -3.296


22 ----- -5.126


21 ----- -9.108
20 ----- -9.175


19 -^-v- -13.34

18 -^-v- -13.60

17 -^-v- -14.25


16 -^-v- -15.64

15 -^-v- -16.13

14 -^-v- -17.12


13 -^-v- -18.37

12 -^-v- -19.19
11 -^-v- -19.26

10 -^-v- -20.00

9 -^-v- -20.75


8 -^-v- -23.63


7 -^-v- -27.01


6 -^-v- -36.02


5 -^-v- -270.8


4 -^-v- -272.4


3 -^-v- -274.2


2 -^-v- -277.7


1 -^-v- -516.3

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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 = -231.6364158269 Hartrees

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