## N,N-dimethylacetamide,CH3C=ON(CH3)2

 H5 | H7 - C4 - H6 H9 \ / N3 - C8 - H11 / \ O1 = C2 H14 H10 \ / C12 - H13 / H15
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=-0.555
C2 charge= 0.552
N3 charge= 0.028
C4 charge=-0.456
H5 charge= 0.155
H6 charge= 0.154
H7 charge= 0.175
C8 charge=-0.447
H9 charge= 0.158
H10 charge= 0.148
H11 charge= 0.158
C12 charge=-0.543
H13 charge= 0.149
H14 charge= 0.149
H15 charge= 0.173
with a dipole moment of 4.11750 Debye

## Bond Lengths:

between O1 and C2: distance=1.244 ang___ between O1 and N3: distance=2.296 ang___
between O1 and C4: distance=2.762 ang___ between C2 and N3: distance=1.384 ang___
between C2 and C12: distance=1.529 ang___ between C2 and H13: distance=2.194 ang___
between C2 and H14: distance=2.195 ang___ between C2 and H15: distance=2.130 ang___
between N3 and C4: distance=1.464 ang___ between N3 and H7: distance=2.086 ang___
between N3 and C8: distance=1.461 ang___ between N3 and H10: distance=2.124 ang___
between N3 and C12: distance=2.495 ang___ between C4 and H5: distance=1.106 ang___
between C4 and H6: distance=1.107 ang___ between C4 and H7: distance=1.100 ang___
between C4 and C8: distance=2.472 ang___ between C8 and H9: distance=1.108 ang___
between C8 and H10: distance=1.099 ang___ between C8 and H11: distance=1.108 ang___
between C8 and C12: distance=2.945 ang___ between C12 and H13: distance=1.105 ang___
between C12 and H14: distance=1.104 ang___ between C12 and H15: distance=1.099 ang___

## Bond Angles:

for N3-C2-O1: angle=121.7 deg___ for C4-N3-C2: angle=119.2 deg___
for H5-C4-N3: angle=110.3 deg___ for H6-C4-N3: angle=110.4 deg___
for H7-C4-N3: angle=108.0 deg___ for C8-N3-C2: angle=125.3 deg___
for H9-C8-N3: angle=110.5 deg___ for H10-C8-N3: angle=111.3 deg___
for H11-C8-N3: angle=110.5 deg___ for C12-C2-O1: angle=120.5 deg___
for H13-C12-C2: angle=111.8 deg___ for H14-C12-C2: angle=111.8 deg___
for H15-C12-C2: angle=107.1 deg___

## Bond Orders (Mulliken):

between O1 and C2: order=1.886___ between O1 and N3: order=-0.164___
between O1 and C4: order=-0.064___ between C2 and N3: order=1.016___
between C2 and C12: order=0.610___ between C2 and H13: order=-0.064___
between C2 and H14: order=-0.064___ between C2 and H15: order=-0.060___
between N3 and C4: order=0.771___ between N3 and H7: order=-0.059___
between N3 and C8: order=0.728___ between N3 and H10: order=-0.084___
between N3 and C12: order=-0.155___ between C4 and H5: order=0.983___
between C4 and H6: order=0.984___ between C4 and H7: order=0.996___
between C4 and C8: order=-0.076___ between C8 and H9: order=0.978___
between C8 and H10: order=1.007___ between C8 and H11: order=0.978___
between C8 and C12: order=-0.054___ between C12 and H13: order=0.992___
between C12 and H14: order=0.992___ between C12 and H15: order=0.997___

## 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 O1-C2 with 1.9947 electrons
__has 63.60% O 1 character in a sp1.62 hybrid
__has 36.40% C 2 character in a sp1.94 hybrid

2. A bonding orbital for O1-C2 with 1.9919 electrons
__has 75.51% O 1 character in a p-pi orbital ( 99.84% p 0.16% d)
__has 24.49% C 2 character in a p-pi orbital ( 99.32% p 0.68% d)

3. A bonding orbital for C2-N3 with 1.9913 electrons
__has 36.54% C 2 character in a sp2.17 hybrid
__has 63.46% N 3 character in a sp1.82 hybrid

4. A bonding orbital for C2-C12 with 1.9878 electrons
__has 49.08% C 2 character in a sp1.86 hybrid
__has 50.92% C12 character in a sp2.74 hybrid

5. A bonding orbital for N3-C4 with 1.9898 electrons
__has 63.45% N 3 character in a sp2.12 hybrid
__has 36.55% C 4 character in a s0.94 p3 hybrid

6. A bonding orbital for N3-C8 with 1.9917 electrons
__has 62.73% N 3 character in a sp2.05 hybrid
__has 37.27% C 8 character in a s0.99 p3 hybrid

7. A bonding orbital for C4-H5 with 1.9925 electrons
__has 58.56% C 4 character in a sp2.98 hybrid
__has 41.44% H 5 character in a s orbital

8. A bonding orbital for C4-H6 with 1.9925 electrons
__has 58.56% C 4 character in a sp2.98 hybrid
__has 41.44% H 6 character in a s orbital

9. A bonding orbital for C4-H7 with 1.9910 electrons
__has 61.68% C 4 character in a sp2.84 hybrid
__has 38.32% H 7 character in a s orbital

10. A bonding orbital for C8-H9 with 1.9927 electrons
__has 58.98% C 8 character in a sp2.99 hybrid
__has 41.02% H 9 character in a s orbital

11. A bonding orbital for C8-H10 with 1.9906 electrons
__has 59.40% C 8 character in a sp2.94 hybrid
__has 40.60% H10 character in a s orbital

12. A bonding orbital for C8-H11 with 1.9926 electrons
__has 58.98% C 8 character in a sp2.99 hybrid
__has 41.02% H11 character in a s orbital

13. A bonding orbital for C12-H13 with 1.9839 electrons
__has 60.00% C12 character in a s0.96 p3 hybrid
__has 40.00% H13 character in a s orbital

14. A bonding orbital for C12-H14 with 1.9840 electrons
__has 60.00% C12 character in a s0.96 p3 hybrid
__has 40.00% H14 character in a s orbital

15. A bonding orbital for C12-H15 with 1.9915 electrons
__has 61.23% C12 character in a s0.98 p3 hybrid
__has 38.77% H15 character in a s orbital

22. A lone pair orbital for O1 with 1.9777 electrons
__made from a sp0.61 hybrid

23. A lone pair orbital for O1 with 1.9004 electrons
__made from a p3 hybrid

24. A lone pair orbital for N3 with 1.7424 electrons
__made from a p-pi orbital ( 99.98% p)

185. A antibonding orbital for O1-C2 with 0.2293 electrons
__has 24.49% O 1 character in a p-pi orbital ( 99.84% p 0.16% d)
__has 75.51% C 2 character in a p-pi orbital ( 99.32% p 0.68% d)

-With core pairs on: O 1 C 2 N 3 C 4 C 8 C12 -

#### 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-C12 with the antibonding acceptor orbital, 188, for N3-C4 is 22.4 kJ/mol.

The interaction of bonding donor orbital, 9, for C4-H7 with the antibonding acceptor orbital, 189, for N3-C8 is 20.9 kJ/mol.

The interaction of bonding donor orbital, 13, for C12-H13 with the second antibonding acceptor orbital, 185, for O1-C2 is 21.8 kJ/mol.

The interaction of bonding donor orbital, 14, for C12-H14 with the second antibonding acceptor orbital, 185, for O1-C2 is 21.4 kJ/mol.

The interaction of bonding donor orbital, 15, for C12-H15 with the antibonding acceptor orbital, 186, for C2-N3 is 22.0 kJ/mol.

The interaction of the second lone pair donor orbital, 23, for O1 with the antibonding acceptor orbital, 186, for C2-N3 is 130. kJ/mol.

The interaction of the second lone pair donor orbital, 23, for O1 with the antibonding acceptor orbital, 187, for C2-C12 is 101. kJ/mol.

The interaction of lone pair donor orbital, 24, for N3 with the second antibonding acceptor orbital, 185, for O1-C2 is 385. kJ/mol.

The interaction of lone pair donor orbital, 24, for N3 with the antibonding acceptor orbital, 190, for C4-H5 is 30.2 kJ/mol.

The interaction of lone pair donor orbital, 24, for N3 with the antibonding acceptor orbital, 191, for C4-H6 is 30.3 kJ/mol.

The interaction of lone pair donor orbital, 24, for N3 with the antibonding acceptor orbital, 193, for C8-H9 is 33.4 kJ/mol.

The interaction of lone pair donor orbital, 24, for N3 with the antibonding acceptor orbital, 195, for C8-H11 is 33.5 kJ/mol.

## 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.

28 ----- 1.535

27 ----- 1.358

26 ----- 1.102

25 ----- -0.544

24 -^-v- -5.632

23 -^-v- -5.749

22 -^-v- -8.519

21 -^-v- -9.067

20 -^-v- -9.538

19 -^-v- -9.758

18 -^-v- -9.870
17 -^-v- -9.884

16 -^-v- -10.46

15 -^-v- -11.59

14 -^-v- -11.83

13 -^-v- -12.16

12 -^-v- -13.45

11 -^-v- -16.65

10 -^-v- -17.76

9 -^-v- -18.48

8 -^-v- -23.09

7 -^-v- -25.36

6 -^-v- -266.3

5 -^-v- -266.9

4 -^-v- -267.4

3 -^-v- -268.8

2 -^-v- -378.3

1 -^-v- -505.2

## 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 = -287.9278525270 Hartrees