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Bounty Ended with 200 reputation awarded by Martin - マーチン♦
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EJC
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I thought about investigating push-pull alkenes. The explosive 1,1–diamino—2,2—dinitroethylene also known as FOX-7 has a double bond with the length 145.6 pm determined by X-ray crystallography:

schematic representation

The evidence is in this publication and CIF. Possibly, carefully designed push-pull alkenes could do even better than this, but I don't have the computer power needed to test it.

Calculations on the B97D3/def2-TZVPP level of theory (Gaussian 09 Rev. E.01) reveal the bond length in the gas phase to be 142.4 pm, which is in quite good agreement of the crystal structure.

molecular structure

E(RB97D3/def2-TZVPP)       =       -598.257208193 
C          0.04916        0.00000       -0.00001
C         -1.37453        0.00031       -0.00000
N          0.80303       -1.22125        0.11237
O          0.24490       -2.28958       -0.23784
O          1.92916       -1.18705        0.58174
N         -2.07141       -1.13253       -0.20314
H         -3.03559       -1.17626        0.08434
H         -1.51303       -1.97791       -0.31069
N         -2.07092        1.13344        0.20315
H         -3.03510        1.17757       -0.08431
H         -1.51218        1.97858        0.31060
N          0.80359        1.22090       -0.11241
O          0.24599        2.28948        0.23787
O          1.92972        1.18619       -0.58172

I thought about investigating push-pull alkenes. The explosive 1,1–diamino—2,2—dinitroethylene also known as FOX-7 has a double bond with the length 145.6 pm determined by X-ray crystallography:

schematic representation

The evidence is in this publication and CIF. Possibly, carefully designed push-pull alkenes could do even better than this, but I don't have the computer power needed to test it.

Calculations on the B97D3/def2-TZVPP level of theory (Gaussian 09 Rev. E.01) reveal the bond length in the gas phase to be 142.4 pm, which is in quite good agreement of the crystal structure.

molecular structure

E(RB97D3/def2-TZVPP)       =       -598.257208193 
C          0.04916        0.00000       -0.00001
C         -1.37453        0.00031       -0.00000
N          0.80303       -1.22125        0.11237
O          0.24490       -2.28958       -0.23784
O          1.92916       -1.18705        0.58174
N         -2.07141       -1.13253       -0.20314
H         -3.03559       -1.17626        0.08434
H         -1.51303       -1.97791       -0.31069
N         -2.07092        1.13344        0.20315
H         -3.03510        1.17757       -0.08431
H         -1.51218        1.97858        0.31060
N          0.80359        1.22090       -0.11241
O          0.24599        2.28948        0.23787
O          1.92972        1.18619       -0.58172

I thought about investigating push-pull alkenes. The explosive 1,1–diamino—2,2—dinitroethylene also known as FOX-7 has a double bond with the length 145.6 pm determined by X-ray crystallography:

schematic representation

The evidence is in this publication and CIF.

Calculations on the B97D3/def2-TZVPP level of theory (Gaussian 09 Rev. E.01) reveal the bond length in the gas phase to be 142.4 pm, which is in quite good agreement of the crystal structure.

molecular structure

E(RB97D3/def2-TZVPP)       =       -598.257208193 
C          0.04916        0.00000       -0.00001
C         -1.37453        0.00031       -0.00000
N          0.80303       -1.22125        0.11237
O          0.24490       -2.28958       -0.23784
O          1.92916       -1.18705        0.58174
N         -2.07141       -1.13253       -0.20314
H         -3.03559       -1.17626        0.08434
H         -1.51303       -1.97791       -0.31069
N         -2.07092        1.13344        0.20315
H         -3.03510        1.17757       -0.08431
H         -1.51218        1.97858        0.31060
N          0.80359        1.22090       -0.11241
O          0.24599        2.28948        0.23787
O          1.92972        1.18619       -0.58172
added computational results
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Martin - マーチン ♦
Martin - マーチン ♦
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I thought about investigating push-pull alkenes. The explosive 1,1–diamino—2,2—dinitroethylene also known as FOX-7 has a double bond with the length 145.6 pm145.6 pm determined by X-ray crystallographyX-ray crystallography:

enter image description hereschematic representation

The evidence is in this publication and CIF. Possibly, carefully designed push-pull alkenes could do even better than this, but I don't have the computer power needed to test it.

Calculations on the B97D3/def2-TZVPP level of theory (Gaussian 09 Rev. E.01) reveal the bond length in the gas phase to be 142.4 pm, which is in quite good agreement of the crystal structure.

molecular structure


E(RB97D3/def2-TZVPP)       =       -598.257208193 
C          0.04916        0.00000       -0.00001
C         -1.37453        0.00031       -0.00000
N          0.80303       -1.22125        0.11237
O          0.24490       -2.28958       -0.23784
O          1.92916       -1.18705        0.58174
N         -2.07141       -1.13253       -0.20314
H         -3.03559       -1.17626        0.08434
H         -1.51303       -1.97791       -0.31069
N         -2.07092        1.13344        0.20315
H         -3.03510        1.17757       -0.08431
H         -1.51218        1.97858        0.31060
N          0.80359        1.22090       -0.11241
O          0.24599        2.28948        0.23787
O          1.92972        1.18619       -0.58172

I thought about investigating push-pull alkenes. The explosive 1,1–diamino—2,2—dinitroethylene also known as FOX-7 has a double bond with the length 145.6 pm determined by X-ray crystallography:

enter image description here

The evidence is in this publication and CIF. Possibly, carefully designed push-pull alkenes could do even better than this, but I don't have the computer power needed to test it.

I thought about investigating push-pull alkenes. The explosive 1,1–diamino—2,2—dinitroethylene also known as FOX-7 has a double bond with the length 145.6 pm determined by X-ray crystallography:

schematic representation

The evidence is in this publication and CIF. Possibly, carefully designed push-pull alkenes could do even better than this, but I don't have the computer power needed to test it.

Calculations on the B97D3/def2-TZVPP level of theory (Gaussian 09 Rev. E.01) reveal the bond length in the gas phase to be 142.4 pm, which is in quite good agreement of the crystal structure.

molecular structure


E(RB97D3/def2-TZVPP)       =       -598.257208193 
C          0.04916        0.00000       -0.00001
C         -1.37453        0.00031       -0.00000
N          0.80303       -1.22125        0.11237
O          0.24490       -2.28958       -0.23784
O          1.92916       -1.18705        0.58174
N         -2.07141       -1.13253       -0.20314
H         -3.03559       -1.17626        0.08434
H         -1.51303       -1.97791       -0.31069
N         -2.07092        1.13344        0.20315
H         -3.03510        1.17757       -0.08431
H         -1.51218        1.97858        0.31060
N          0.80359        1.22090       -0.11241
O          0.24599        2.28948        0.23787
O          1.92972        1.18619       -0.58172
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EJC
EJC
  • 14.4k
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  • 69
  • 157

I thought about investigating push-pull alkenes. The explosive 1,1–diamino—2,2—dinitroethylene also known as FOX-7 has a double bond with the length 145.6 pm determined by X-ray crystallography:

enter image description here

The evidence is in this publication and CIF. Possibly, carefully designed push-pull alkenes could do even better than this, but I don't have the computer power needed to test it.