Exercise 9

Partial π-Electronic Bond Order between two neighboring atoms

Full π-Electronic Bond Order between two neighboring atoms
Theoretical Organic Chemistry, 2013

Anastazija Ristovska

Atom 1 Atom 2 Atom 3 Atom 4 Atom 5 Atom 6 Atom 7 Atom 8 Atom 9 Atom10
MO 10 0.096 0.137 0.349 -0.543 -0.207 -0.295 0.497 -0.231 0.322 -0.150
MO 9 0.318 -0.287 0.403 -0.127 -0.479 0.432 -0.363 0.241 0.151 -0.100
MO 8 0.349 0.212 0.171 0.217 -0.427 -0.259 0.104 -0.085 -0.541 0.443
MO 7 0.173 0.563 -0.088 0.182 -0.121 -0.394 -0.288 0.412 0.249 -0.357
MO 6 0.487 -0.192 -0.423 0.330 -0.176 0.069 0.166 -0.495 0.137 -0.380
MO 5 0.487 -0.192 -0.423 -0.330 0.176 -0.069 0.166 0.495 0.138 0.380
MO 4 0.173 0.563 -0.088 -0.182 0.121 0.394 -0.288 -0.412 0.249 0.357
MO 3 0.349 0.212 0.171 -0.217 0.427 0.259 0.104 0.085 -0.541 -0.443
MO 2 0.318 -0.287 0.403 0.127 0.479 -0.432 -0.363 -0.241 0.151 0.100
MO 1 0.096 0.137 0.349 0.543 0.207 0.295 0.497 0.231 0.322 0.150

𝑝𝑟𝑠 = ∑ g 𝑖 𝑐𝑖𝑟 𝑐𝑖𝑠

𝑖=1

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Where 𝑐𝑖𝑟 is the coefficient of atom 𝑟 in the molecular orbital 𝑖, 𝑐𝑖𝑠 is the coefficient of atom 𝑠 in the
molecular orbital 𝑖, g 𝑖 is the number of atoms in the MO 𝑖, 𝑝𝑟𝑠 is the full π-electronic bond order
𝑖
between neighboring atoms 𝑠 and 𝑟, and is the sum of 𝑝𝑟𝑠 i.e. the partial π-electronic bond order between
atoms 𝑠 and 𝑟 for the MO 𝑖.

The partial π-electronic bond orders of the between atoms 1 and 2 for the molecular orbitals ψ1, ψ2, ψ3,
etc. are all zero since atoms 1 and 2 are not bonded to each other. The only atom pairs that form bonds
are: C2-C6, C9-C10, C1-C5, C7-C8, C3-C4, C3-C5, C4-C9, C6-C7, and C4-C7; a total of nine bonds.

Atom 1 Atom 2 Atom 3 Atom 4 Atom 5 Atom 6 Atom 7 Atom 8 Atom 9 Atom10
MO 10 0.096 0.137 0.349 -0.543 -0.207 -0.295 0.497 -0.231 0.322 -0.150
MO 9 0.318 -0.287 0.403 -0.127 -0.479 0.432 -0.363 0.241 0.151 -0.100
MO 8 0.349 0.212 0.171 0.217 -0.427 -0.259 0.104 -0.085 -0.541 0.443
MO 7 0.173 0.563 -0.088 0.182 -0.121 -0.394 -0.288 0.412 0.249 -0.357
MO 6 0.487 -0.192 -0.423 0.330 -0.176 0.069 0.166 -0.495 0.137 -0.380
MO 5 0.487 -0.192 -0.423 -0.330 0.176 -0.069 0.166 0.495 0.138 0.380
MO 4 0.173 0.563 -0.088 -0.182 0.121 0.394 -0.288 -0.412 0.249 0.357
MO 3 0.349 0.212 0.171 -0.217 0.427 0.259 0.104 0.085 -0.541 -0.443
MO 2 0.318 -0.287 0.403 0.127 0.479 -0.432 -0.363 -0.241 0.151 0.100
MO 1 0.096 0.137 0.349 0.543 0.207 0.295 0.497 0.231 0.322 0.150

The partial π-electronic bond orders of the bond between atoms 3 and 4 for the molecular orbitals ψ10, ψ9,
ψ8, etc. are:
10
ψ10: 𝑝34 = 0*0.349*(-0.543) = 0
9
ψ9: 𝑝34 = 0*0.403*(-0.127) = 0
8 0*0.171*0.217 = 0
ψ8: 𝑝34 =
7 0*(-0.088)*0.182 = 0
ψ7: 𝑝34 =
6 0*(-0.423)*0.330 = 0
ψ6: 𝑝34 =
5 2*(-0.423)*(-0.330) = 0.279180
ψ5: 𝑝34 =
4 2*(-0.088)*(-0.182) = 0.032032
ψ4: 𝑝34 =
3 2*0.171*(-0.217) = -0.074214
ψ3: 𝑝34 =
2 2*0.403*0.127 = 0.102362
ψ2: 𝑝34 =
1 2*0.349*0.543 = 0.379014
ψ1: 𝑝34 =

The full π-electronic bond order of the bond between atoms 3 and 4 is 0,718374. The manually-calculated
value differs by 0.0014 from the value displayed in the Huckel-C program bond-order calculation table,
0.717.

Atom 1 Atom 2 Atom 3 Atom 4 Atom 5 Atom 6 Atom 7 Atom 8 Atom 9 Atom10
MO 10 0.096 0.137 0.349 -0.543 -0.207 -0.295 0.497 -0.231 0.322 -0.150
MO 9 0.318 -0.287 0.403 -0.127 -0.479 0.432 -0.363 0.241 0.151 -0.100
MO 8 0.349 0.212 0.171 0.217 -0.427 -0.259 0.104 -0.085 -0.541 0.443
MO 7 0.173 0.563 -0.088 0.182 -0.121 -0.394 -0.288 0.412 0.249 -0.357
MO 6 0.487 -0.192 -0.423 0.330 -0.176 0.069 0.166 -0.495 0.137 -0.380
MO 5 0.487 -0.192 -0.423 -0.330 0.176 -0.069 0.166 0.495 0.138 0.380
MO 4 0.173 0.563 -0.088 -0.182 0.121 0.394 -0.288 -0.412 0.249 0.357
MO 3 0.349 0.212 0.171 -0.217 0.427 0.259 0.104 0.085 -0.541 -0.443
MO 2 0.318 -0.287 0.403 0.127 0.479 -0.432 -0.363 -0.241 0.151 0.100
MO 1 0.096 0.137 0.349 0.543 0.207 0.295 0.497 0.231 0.322 0.150

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The partial π-electronic bond orders of the bond between atoms 2 and 6 for the molecular orbitals ψ10, ψ9,
ψ8, etc. are:
10
ψ10: 𝑝26 = 0*0.137*(-0.295) = 0
9
ψ9: 𝑝26 = 0*(-287)*0.432 = 0
8 0*0.212*(-0.259) = 0
ψ8: 𝑝26 =
7 0*0.563*(-0.394) = 0
ψ7: 𝑝26 =
6 0*(-0.192)*0.069 = 0
ψ6: 𝑝26 =
5 2*(-0.192)*(-0.069) = 0.026496
ψ5: 𝑝26 =
4 2*0.563*0.394 = 0.443644
ψ4: 𝑝26 =
3 2*0.212*0.259 = 0.109816
ψ3: 𝑝26 =
2 2*(-0.287)*(-0.432) = 0.247968
ψ2: 𝑝26 =
1 2*0.137*0.295 = 0.080830
ψ1: 𝑝26 =

The full π-electronic bond order of the bond between atoms 2 and 6 is 0.9087076. The manually-
calculated value is almost the same as the value displayed in the Huckel-C program bond-order
calculation table, 0.908.

Atom 1 Atom 2 Atom 3 Atom 4 Atom 5 Atom 6 Atom 7 Atom 8 Atom 9 Atom10
MO 10 0.096 0.137 0.349 -0.543 -0.207 -0.295 0.497 -0.231 0.322 -0.150
MO 9 0.318 -0.287 0.403 -0.127 -0.479 0.432 -0.363 0.241 0.151 -0.100
MO 8 0.349 0.212 0.171 0.217 -0.427 -0.259 0.104 -0.085 -0.541 0.443
MO 7 0.173 0.563 -0.088 0.182 -0.121 -0.394 -0.288 0.412 0.249 -0.357
MO 6 0.487 -0.192 -0.423 0.330 -0.176 0.069 0.166 -0.495 0.137 -0.380
MO 5 0.487 -0.192 -0.423 -0.330 0.176 -0.069 0.166 0.495 0.138 0.380
MO 4 0.173 0.563 -0.088 -0.182 0.121 0.394 -0.288 -0.412 0.249 0.357
MO 3 0.349 0.212 0.171 -0.217 0.427 0.259 0.104 0.085 -0.541 -0.443
MO 2 0.318 -0.287 0.403 0.127 0.479 -0.432 -0.363 -0.241 0.151 0.100
MO 1 0.096 0.137 0.349 0.543 0.207 0.295 0.497 0.231 0.322 0.150

The partial π-electronic bond orders of the bond between atoms 9 and 10 for the molecular orbitals ψ10,
ψ9, ψ8, etc. are:
10
ψ10: 𝑝9−10 = 0*0.322*(-0.150) = 0
9
ψ9: 𝑝9−10 = 0*0.151*(-0.100) = 0
8 0*(-0.541)*0.443 = 0
ψ8: 𝑝9−10 =
7 0*0.249*(-0.357) = 0
ψ7: 𝑝9−10 =
6 0*0.137*(-0.380) = 0
ψ6: 𝑝9−10 =
5 2*0.138*0.380 = 0.104880
ψ5: 𝑝9−10 =
4 2*0.249*0.357 = 0.177786
ψ4: 𝑝9−10 =
3 2*(-0.541)*(-0.443) = 0.479326
ψ3: 𝑝9−10 =
2 2*0.151*0.100 = 0.030200
ψ2: 𝑝9−10 =
1 2*0.322*0.150 = 0.096600
ψ1: 𝑝9−10 =

The full π-electronic bond order of the bond between atoms 9 and 10 is 0.888792. The manually-
calculated value is almost the same as the value displayed in the Huckel-C program bond-order
calculation table, 0.888.

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 Atom 1 Atom 2 Atom 3 Atom 4 Atom 5 Atom 6 Atom 7 Atom 8 Atom 9 Atom10
MO 10 0.096 0.137 0.349 -0.543 -0.207 -0.295 0.497 -0.231 0.322 -0.150
MO 9 0.318 -0.287 0.403 -0.127 -0.479 0.432 -0.363 0.241 0.151 -0.100
MO 8 0.349 0.212 0.171 0.217 -0.427 -0.259 0.104 -0.085 -0.541 0.443
MO 7 0.173 0.563 -0.088 0.182 -0.121 -0.394 -0.288 0.412 0.249 -0.357
MO 6 0.487 -0.192 -0.423 0.330 -0.176 0.069 0.166 -0.495 0.137 -0.380
MO 5 0.487 -0.192 -0.423 -0.330 0.176 -0.069 0.166 0.495 0.138 0.380
MO 4 0.173 0.563 -0.088 -0.182 0.121 0.394 -0.288 -0.412 0.249 0.357
MO 3 0.349 0.212 0.171 -0.217 0.427 0.259 0.104 0.085 -0.541 -0.443
MO 2 0.318 -0.287 0.403 0.127 0.479 -0.432 -0.363 -0.241 0.151 0.100
MO 1 0.096 0.137 0.349 0.543 0.207 0.295 0.497 0.231 0.322 0.150

The partial π-electronic bond orders of the bond between atoms 1 and 5 for the molecular orbitals ψ10, ψ9,
ψ8, etc. are:
10
ψ10: 𝑝15 = 0*0.096*(-0.207) = 0
9
ψ9: 𝑝15 = 0*0.318*(-0.479) = 0
8 0*0.349*(-0.427) = 0
ψ8: 𝑝15 =
7 0*0.173*(-0.121) = 0
ψ7: 𝑝15 =
6 0*0.487*(-0.176) = 0
ψ6: 𝑝15 =
5 2*0.487*0.176 = 0.171424
ψ5: 𝑝15 =
4 2*0.173*0.121 = 0.041866
ψ4: 𝑝15 =
3 2*0.349*0.427 = 0.298046
ψ3: 𝑝15 =
2 2*0.318*0.479 = 0.304644
ψ2: 𝑝15 =
1 2*0.096*0.207 = 0.039744
ψ1: 𝑝15 =

The full π-electronic bond order of the bond between atoms 1 and 5 is 0.855724. The manually-calculated
value differs by 0.0013 from the value displayed in the Huckel-C program bond-order calculation table,
0.857.

Atom 1 Atom 2 Atom 3 Atom 4 Atom 5 Atom 6 Atom 7 Atom 8 Atom 9 Atom10
MO 10 0.096 0.137 0.349 -0.543 -0.207 -0.295 0.497 -0.231 0.322 -0.150
MO 9 0.318 -0.287 0.403 -0.127 -0.479 0.432 -0.363 0.241 0.151 -0.100
MO 8 0.349 0.212 0.171 0.217 -0.427 -0.259 0.104 -0.085 -0.541 0.443
MO 7 0.173 0.563 -0.088 0.182 -0.121 -0.394 -0.288 0.412 0.249 -0.357
MO 6 0.487 -0.192 -0.423 0.330 -0.176 0.069 0.166 -0.495 0.137 -0.380
MO 5 0.487 -0.192 -0.423 -0.330 0.176 -0.069 0.166 0.495 0.138 0.380
MO 4 0.173 0.563 -0.088 -0.182 0.121 0.394 -0.288 -0.412 0.249 0.357
MO 3 0.349 0.212 0.171 -0.217 0.427 0.259 0.104 0.085 -0.541 -0.443
MO 2 0.318 -0.287 0.403 0.127 0.479 -0.432 -0.363 -0.241 0.151 0.100
MO 1 0.096 0.137 0.349 0.543 0.207 0.295 0.497 0.231 0.322 0.150

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The partial π-electronic bond orders of the bond between atoms 7 and 8 for the molecular orbitals ψ10, ψ9,
ψ8, etc. are:
10
ψ10: 𝑝78 = 0*0.497*(-0.231) = 0
9
ψ9: 𝑝78 = 0*(-0.363)*0.241 = 0
8 0*0.104*(-0.085) = 0
ψ8: 𝑝78 =
7 0*(-0.288)*0.412 = 0
ψ7: 𝑝78 =
6 0*0.166*(-0.495) = 0
ψ6: 𝑝78 =
5 2*0.166*0.495 = 0.164340
ψ5: 𝑝78 =
4 2*(-0.288)*(-0.412) = 0.237312
ψ4: 𝑝78 =
3 2*0.104*0.085 = 0.017680
ψ3: 𝑝78 =
2 2*(-0.363)*(-0.241) = 0.174966
ψ2: 𝑝78 =
1 2*0.497*0.231 = 0.229614
ψ1: 𝑝78 =

The full π-electronic bond order of the bond between atoms 7 and 8 is 0.823912. The manually-calculated
value differs by 0.011 from the value displayed in the Huckel-C program bond-order calculation table,
0.813.

Atom 1 Atom 2 Atom 3 Atom 4 Atom 5 Atom 6 Atom 7 Atom 8 Atom 9 Atom10
MO 10 0.096 0.137 0.349 -0.543 -0.207 -0.295 0.497 -0.231 0.322 -0.150
MO 9 0.318 -0.287 0.403 -0.127 -0.479 0.432 -0.363 0.241 0.151 -0.100
MO 8 0.349 0.212 0.171 0.217 -0.427 -0.259 0.104 -0.085 -0.541 0.443
MO 7 0.173 0.563 -0.088 0.182 -0.121 -0.394 -0.288 0.412 0.249 -0.357
MO 6 0.487 -0.192 -0.423 0.330 -0.176 0.069 0.166 -0.495 0.137 -0.380
MO 5 0.487 -0.192 -0.423 -0.330 0.176 -0.069 0.166 0.495 0.138 0.380
MO 4 0.173 0.563 -0.088 -0.182 0.121 0.394 -0.288 -0.412 0.249 0.357
MO 3 0.349 0.212 0.171 -0.217 0.427 0.259 0.104 0.085 -0.541 -0.443
MO 2 0.318 -0.287 0.403 0.127 0.479 -0.432 -0.363 -0.241 0.151 0.100
MO 1 0.096 0.137 0.349 0.543 0.207 0.295 0.497 0.231 0.322 0.150

The partial π-electronic bond orders of the bond between atoms 3 and 5 for the molecular orbitals ψ10, ψ9,
ψ8, etc. are:
10
ψ10: 𝑝35 = 0*0.349*(-0.207) = 0
9
ψ9: 𝑝35 = 0*0.403*(-0.479) = 0
8 0*0.171*(-0.427) = 0
ψ8: 𝑝35 =
7 0*(-0.088)*(-0.121) = 0
ψ7: 𝑝35 =
6 0*(-0.423)*(-0.176) = 0
ψ6: 𝑝35 =
5 2*(-0.423)*0.176 = -0.148896
ψ5: 𝑝35 =
4 2*(-0.088)*0.121 = -0.021296
ψ4: 𝑝35 =
3 2*0.171*0.427 = 0.146034
ψ3: 𝑝35 =
2 2*0.403*0.479 = 0.386074
ψ2: 𝑝35 =
1 2*0.349*0.207 = 0.144486
ψ1: 𝑝35 =

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The full π-electronic bond order of the bond between atoms 3 and 5 is 0.506402. The manually-calculated
value differs only slightly from the value displayed in the Huckel-C program bond-order calculation table,
0.505.

Atom 1 Atom 2 Atom 3 Atom 4 Atom 5 Atom 6 Atom 7 Atom 8 Atom 9 Atom10
MO 10 0.096 0.137 0.349 -0.543 -0.207 -0.295 0.497 -0.231 0.322 -0.150
MO 9 0.318 -0.287 0.403 -0.127 -0.479 0.432 -0.363 0.241 0.151 -0.100
MO 8 0.349 0.212 0.171 0.217 -0.427 -0.259 0.104 -0.085 -0.541 0.443
MO 7 0.173 0.563 -0.088 0.182 -0.121 -0.394 -0.288 0.412 0.249 -0.357
MO 6 0.487 -0.192 -0.423 0.330 -0.176 0.069 0.166 -0.495 0.137 -0.380
MO 5 0.487 -0.192 -0.423 -0.330 0.176 -0.069 0.166 0.495 0.138 0.380
MO 4 0.173 0.563 -0.088 -0.182 0.121 0.394 -0.288 -0.412 0.249 0.357
MO 3 0.349 0.212 0.171 -0.217 0.427 0.259 0.104 0.085 -0.541 -0.443
MO 2 0.318 -0.287 0.403 0.127 0.479 -0.432 -0.363 -0.241 0.151 0.100
MO 1 0.096 0.137 0.349 0.543 0.207 0.295 0.497 0.231 0.322 0.150

The partial π-electronic bond orders of the bond between atoms 4 and 9 for the molecular orbitals ψ10, ψ9,
ψ8, etc. are:
10
ψ10: 𝑝49 = 0*(-0.543)*0.322= 0
9
ψ9: 𝑝49 = 0*(-0.127)*0.151= 0
8 0*0.217*(-0.541)= 0
ψ8: 𝑝49 =
7 0*0.182*0.249= 0
ψ7: 𝑝49 =
6 0*0.330*0.137= 0
ψ6: 𝑝49 =
5 2*(-0.330)*0.138= -0.091080
ψ5: 𝑝49 =
4 2*(-0.182)*0.249= -0.090636
ψ4: 𝑝49 =
3 2*(-0.217)*(-0.541)= 0.234794
ψ3: 𝑝49 =
2 2*0.127*0.151= 0.038354
ψ2: 𝑝49 =
1 2*0.543*0.322= 0.349692
ψ1: 𝑝49 =

The full π-electronic bond order of the bond between atoms 4 and 9 is 0.441124. The manually-calculated
value is the same as the value displayed in the Huckel-C program bond-order calculation table, 0.441.

Atom 1 Atom 2 Atom 3 Atom 4 Atom 5 Atom 6 Atom 7 Atom 8 Atom 9 Atom10
MO 10 0.096 0.137 0.349 -0.543 -0.207 -0.295 0.497 -0.231 0.322 -0.150
MO 9 0.318 -0.287 0.403 -0.127 -0.479 0.432 -0.363 0.241 0.151 -0.100
MO 8 0.349 0.212 0.171 0.217 -0.427 -0.259 0.104 -0.085 -0.541 0.443
MO 7 0.173 0.563 -0.088 0.182 -0.121 -0.394 -0.288 0.412 0.249 -0.357
MO 6 0.487 -0.192 -0.423 0.330 -0.176 0.069 0.166 -0.495 0.137 -0.380
MO 5 0.487 -0.192 -0.423 -0.330 0.176 -0.069 0.166 0.495 0.138 0.380
MO 4 0.173 0.563 -0.088 -0.182 0.121 0.394 -0.288 -0.412 0.249 0.357
MO 3 0.349 0.212 0.171 -0.217 0.427 0.259 0.104 0.085 -0.541 -0.443
MO 2 0.318 -0.287 0.403 0.127 0.479 -0.432 -0.363 -0.241 0.151 0.100
MO 1 0.096 0.137 0.349 0.543 0.207 0.295 0.497 0.231 0.322 0.150

The partial π-electronic bond orders of the bond between atoms 4 and 7 for the molecular orbitals ψ10, ψ9,
ψ8, etc. are:

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 10
ψ10: 𝑝47 = 0*(-0.543)*0.497= 0
9
ψ9: 𝑝47 = 0*(-0.127)*(-0.363)= 0
8 0*0.217*0.104= 0
ψ8: 𝑝47 =
7 0*0.182*(-0.288)= 0
ψ7: 𝑝47 =
6 0*0.330*0.166= 0
ψ6: 𝑝47 =
5 2*(-0.330)*0.166= -0.109560
ψ5: 𝑝47 =
4 2*(-0.182)*(-0.288)= 0.104832
ψ4: 𝑝47 =
3 2*(-0.217)*0.104= -0.045136
ψ3: 𝑝47 =
2 2*0.127*(-0.363)= -0.092202
ψ2: 𝑝47 =
1 2*0.543*0.497= 0.539742
ψ1: 𝑝47 =

The full π-electronic bond order of the bond between atoms 4 and 7 is 0.397676. The manually-calculated
value is the same as the value displayed in the Huckel-C program bond-order calculation table, 0.397.

Atom 1 Atom 2 Atom 3 Atom 4 Atom 5 Atom 6 Atom 7 Atom 8 Atom 9 Atom10
MO 10 0.096 0.137 0.349 -0.543 -0.207 -0.295 0.497 -0.231 0.322 -0.150
MO 9 0.318 -0.287 0.403 -0.127 -0.479 0.432 -0.363 0.241 0.151 -0.100
MO 8 0.349 0.212 0.171 0.217 -0.427 -0.259 0.104 -0.085 -0.541 0.443
MO 7 0.173 0.563 -0.088 0.182 -0.121 -0.394 -0.288 0.412 0.249 -0.357
MO 6 0.487 -0.192 -0.423 0.330 -0.176 0.069 0.166 -0.495 0.137 -0.380
MO 5 0.487 -0.192 -0.423 -0.330 0.176 -0.069 0.166 0.495 0.138 0.380
MO 4 0.173 0.563 -0.088 -0.182 0.121 0.394 -0.288 -0.412 0.249 0.357
MO 3 0.349 0.212 0.171 -0.217 0.427 0.259 0.104 0.085 -0.541 -0.443
MO 2 0.318 -0.287 0.403 0.127 0.479 -0.432 -0.363 -0.241 0.151 0.100
MO 1 0.096 0.137 0.349 0.543 0.207 0.295 0.497 0.231 0.322 0.150

The partial π-electronic bond orders of the bond between atoms 6 and 7 for the molecular orbitals ψ10, ψ9,
ψ8, etc. are:
10
ψ10: 𝑝67 = 0*(-0.295)*0.497= 0
9
ψ9: 𝑝67 = 0*0.432*(-0.363)= 0
8 0*(-0.259)*0.104= 0
ψ8: 𝑝67 =
7 0*(-0.394)*(-0.288)= 0
ψ7: 𝑝67 =
6 0*0.069*0.166= 0
ψ6: 𝑝67 =
5 2*(-0.069)*0.166= -0.022908
ψ5: 𝑝67 =
4 2*0.394*(-0.288)= -0.226944
ψ4: 𝑝67 =
3 2*0.259*0.104= 0.053872
ψ3: 𝑝67 =
2 2*(-0.432)*(-0.363)= 0.313632
ψ2: 𝑝67 =
1 2*0.295*0.497= 0.293230
ψ1: 𝑝67 =

The full π-electronic bond order of the bond between atoms 6 and 7 is 0.410882. The manually-calculated
value is the same as the value displayed in the Huckel-C program bond-order calculation table, 0.410.

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Computer software-calculated values (Huckel-C):

Atom Bond Order Type of

1 Pair
C2-C6 0.908 Bond
Double
2 C9-C10 0.888 Double
3 C1-C5 0.857 Double
4 C7-C8 0.813 Double
5 C3-C4 0.717 Double
6 C3-C5 0.505 Single
7 C4-C9 0.441 Single
8 C6-C7 0.410 Single
9 C4-C7 0.397 Single

8
All calculations were conducted using the Huckel Molecular Orbitals (HMO) Calculations computer
program, Copyright 1993 by David R. Anderson, Department of Chemistry, University of Colorado,
Colorado Springs, CO 80933.