N-methylacetamide, CH3C=ONHCH3

H8H6
\ |
N3 - C4 - H5
/ \
O1 = C2H12H7
\ /
C9 - H11
/
H10
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=-0.594
C2 charge= 0.681
N3 charge=-0.508
C4 charge=-0.147
H5 charge= 0.093
H6 charge= 0.119
H7 charge= 0.084
H8 charge= 0.324
C9 charge=-0.515
H10 charge= 0.160
H11 charge= 0.148
H12 charge= 0.154
with a dipole moment of 4.34843 Debye

Bond Lengths:

between O1 and C2: distance=1.240 ang___ between O1 and N3: distance=2.280 ang___
between C2 and N3: distance=1.380 ang___ between C2 and C9: distance=1.525 ang___
between C2 and H10: distance=2.139 ang___ between C2 and H12: distance=2.184 ang___
between N3 and C4: distance=1.464 ang___ between N3 and H8: distance=1.022 ang___
between N3 and C9: distance=2.476 ang___ between C4 and H5: distance=1.108 ang___
between C4 and H6: distance=1.101 ang___ between C4 and H7: distance=1.103 ang___
between C9 and H10: distance=1.099 ang___ between C9 and H11: distance=1.105 ang___
between C9 and H12: distance=1.105 ang___

Bond Angles:

for N3-C2-O1: angle=120.8 deg___ for C4-N3-C2: angle=126.6 deg___
for H5-C4-N3: angle=112.5 deg___ for H6-C4-N3: angle=109.0 deg___
for H7-C4-N3: angle=111.0 deg___ for H8-N3-C2: angle=113.4 deg___
for C9-C2-O1: angle=122.3 deg___ for H10-C9-C2: angle=108.0 deg___
for H11-C9-C2: angle=111.4 deg___ for H12-C9-C2: angle=111.2 deg___

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Bond Orders (Mulliken):

between O1 and C2: order=1.825___ between O1 and N3: order=-0.125___
between C2 and N3: order=1.086___ between C2 and C9: order=0.708___
between C2 and H10: order=-0.057___ between C2 and H12: order=-0.060___
between N3 and C4: order=0.776___ between N3 and H8: order=0.884___
between N3 and C9: order=-0.163___ between C4 and H5: order=0.971___
between C4 and H6: order=0.990___ between C4 and H7: order=0.980___
between C9 and H10: order=1.001___ between C9 and H11: order=0.960___
between C9 and H12: order=0.991___

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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 O1-C2 with 1.9946 electrons
__has 63.69% O 1 character in a sp1.67 hybrid
__has 36.31% C 2 character in a sp1.96 hybrid

2. A bonding orbital for O1-C2 with 1.9919 electrons
__has 74.85% O 1 character in a p3 hybrid
__has 25.15% C 2 character in a p3 hybrid

3. A bonding orbital for C2-N3 with 1.9942 electrons
__has 37.41% C 2 character in a sp2.20 hybrid
__has 62.59% N 3 character in a sp1.76 hybrid

4. A bonding orbital for C2-C9 with 1.9901 electrons
__has 48.86% C 2 character in a sp1.88 hybrid
__has 51.14% C 9 character in a sp2.76 hybrid

5. A bonding orbital for N3-C4 with 1.9934 electrons
__has 62.11% N 3 character in a sp1.84 hybrid
__has 37.89% C 4 character in a sp2.92 hybrid

6. A bonding orbital for N3-H8 with 1.9859 electrons
__has 70.56% N 3 character in a sp2.61 hybrid
__has 29.44% H 8 character in a s orbital

7. A bonding orbital for C4-H5 with 1.9945 electrons
__has 58.76% C 4 character in a sp2.96 hybrid
__has 41.24% H 5 character in a s orbital

8. A bonding orbital for C4-H6 with 1.9919 electrons
__has 59.46% C 4 character in a s0.98 p3 hybrid
__has 40.54% H 6 character in a s orbital

9. A bonding orbital for C4-H7 with 1.9924 electrons
__has 59.12% C 4 character in a s0.99 p3 hybrid
__has 40.88% H 7 character in a s orbital

10. A bonding orbital for C9-H10 with 1.9918 electrons
__has 61.22% C 9 character in a sp2.98 hybrid
__has 38.78% H10 character in a s orbital

11. A bonding orbital for C9-H11 with 1.9836 electrons
__has 60.03% C 9 character in a s0.96 p3 hybrid
__has 39.97% H11 character in a s orbital

12. A bonding orbital for C9-H12 with 1.9827 electrons
__has 60.11% C 9 character in a s0.96 p3 hybrid
__has 39.89% H12 character in a s orbital

18. A lone pair orbital for O1 with 1.9778 electrons
__made from a sp0.61 hybrid

19. A lone pair orbital for O1 with 1.9014 electrons
__made from a p3 hybrid

20. A lone pair orbital for N3 with 1.7842 electrons
__made from a p3 hybrid

152. A antibonding orbital for O1-C2 with 0.2048 electrons
__has 25.15% O 1 character in a p3 hybrid
__has 74.85% C 2 character in a p3 hybrid

-With core pairs on: O 1 C 2 N 3 C 4 C 9 -

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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, 6, for N3-H8 with the antibonding acceptor orbital, 154, for C2-C9 is 23.0 kJ/mol.

The interaction of bonding donor orbital, 10, for C9-H10 with the antibonding acceptor orbital, 153, for C2-N3 is 21.4 kJ/mol.

The interaction of bonding donor orbital, 11, for C9-H11 with the second antibonding acceptor orbital, 152, for O1-C2 is 26.4 kJ/mol.

The interaction of the second lone pair donor orbital, 19, for O1 with the antibonding acceptor orbital, 153, for C2-N3 is 129. kJ/mol.

The interaction of the second lone pair donor orbital, 19, for O1 with the antibonding acceptor orbital, 154, for C2-C9 is 107. kJ/mol.

The interaction of lone pair donor orbital, 20, for N3 with the second antibonding acceptor orbital, 152, for O1-C2 is 336. kJ/mol.

The interaction of lone pair donor orbital, 20, for N3 with the antibonding acceptor orbital, 157, for C4-H5 is 46.5 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.

24 ----- 1.565

23 ----- 1.266

22 ----- 0.929


21 ----- -0.660


20 -^-v- -5.685

19 -^-v- -6.093


18 -^-v- -8.757

17 -^-v- -9.481

16 -^-v- -9.721

15 -^-v- -9.940

14 -^-v- -10.37


13 -^-v- -11.48

12 -^-v- -11.65

11 -^-v- -12.36


10 -^-v- -14.35


9 -^-v- -17.51

8 -^-v- -18.22


7 -^-v- -22.77


6 -^-v- -25.41


5 -^-v- -266.4


4 -^-v- -267.5


3 -^-v- -268.9


2 -^-v- -378.1


1 -^-v- -505.3

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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 = -248.6108328618 Hartrees

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