Exercise 10 - Bond Length Calculated from the -Electron Bond Order

Theoretical Organic Chemistry, 2013

Anastazija Ristovska
The bond length between two particular carbon atoms in compound A is given by:
() = 1,518 0,180 , where is the -electron bond order. The total bond order is
calculated by adding 1 for the bond if it is known that the bond is made of both a bond as well as a
bond. In any case, the formula used for calculating bond distances is not affected in any way when a
bond is present. From the previous assignment we calculated the partial as well as full bond orders of
our molecule. For calculating the bond lengths we will only use the full bond orders (as we have
calculated them, and not as given by the computer software).

The full -electronic bond order of the bond between atoms 3 and 4 is 0,718374. Therefore the bond
length 34() is 34() = 1,518 0,180 0,718374=1,38869.
The full -electronic bond order of the bond between atoms 2 and 6 is 0,9087076. Therefore the bond
length 26() is 26() = 1,518 0,180 0,908708=1,35443.
The full -electronic bond order of the bond between atoms 9 and 10 is 0,888792. Therefore the bond
length 910() is 910() = 1,518 0,180 0,888792=1,35802.
The full -electronic bond order of the bond between atoms 1 and 5 is 0,855724. Therefore the bond
length 15() is 15() = 1,518 0,180 0,855724=1,36397.
The full -electronic bond order of the bond between atoms 7 and 8 is 0,823912. Therefore the bond
length 78() is 78() = 1,518 0,180 0,823912=1,36970.
The full -electronic bond order of the bond between atoms 3 and 5 is 0,506402. Therefore the bond
length 35() is 35() = 1,518 0,180 0,506402=1,42685.
The full -electronic bond order of the bond between atoms 4 and 9 is 0,441124. Therefore the bond
length 49() is 49() = 1,518 0,180 0,441124=1,43860.
The full -electronic bond order of the bond between atoms 4 and 7 is 0,397676. Therefore the bond
length 47() is 47() = 1,518 0,180 0,397676=1,44642.
The full -electronic bond order of the bond between atoms 6 and 7 is 0,410882. Therefore the bond
length 67() is 67() = 1,518 0,180 0,410882=1,44404.
1

1,46
0,397676; 1,44642
0,410882; 1,44404
0,441124; 1,4386

1,44

0,506402; 1,42685
bond length ()

Bond Length ()

1,42

1,4
0,718374; 1,38869
1,38

1,36

y = -0,180x + 1,518
R = 1

0,823912; 1,3697
0,855724; 1,36397
0,888792; 1,35802
0,9087076; 1,35443

1,34
0

0,2

0,4

0,6

0,8

-Electron Bond Order

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.