Basic Concepts of Chemical Bonding
Strengths of Covalent Bonds
Strengths of Covalent Bonds
The stability of a molecule is a function of the strength of the covalent bonds holding the atoms together.
How do we measure the strength of a covalent bond?
Bond-dissociation energy (i.e. "bond energy")
Bond energy is the enthalpy change (DH, heat input) required to break a bond (in 1 mole of a gaseous substance)
What about when we have a compound which is not a diatomic molecule? Consider the dissociation of methane:
There are four equivalent C-H bonds, thus we can that the dissociation energy for a single C-H bond would be:
D(C-H) = (1660/4) kJ/mol = 415 kJ/mol
Note:
Bond energy is always a positive value - it takes energy to break a covalent bond (conversely energy is released during bond formation)
Average bond energies:
|
Bond |
(kJ/mol) |
|
C-F |
485 |
|
C-Cl |
328 |
|
C-Br |
276 |
|
C-I |
240 |
|
|
|
|
C-C |
348 |
|
C-N |
293 |
|
C-O |
358 |
|
C-F |
485 |
|
|
|
|
C-C |
348 |
|
C=C |
614 |
|
C=C |
839 |
The more stable a molecule (i.e. the stronger the bonds) the less likely the molecule is to undergo a chemical reaction
Bond Energies and the Enthalpy of Reactions
If we know which bonds are broken and which bonds are made during a chemical reaction, we can estimate the enthalpy change of the reaction (DHrxn) even if we don't know the enthalpies of formation (DHf°)for the reactants and products:
D
H = S(bond energies of broken bonds) - S(bond energies of formed bonds)Example: The reaction between 1 mol of chlorine and 1 mol methane
Bonds broken: 1 mol of Cl-Cl bonds, 1 mol of C-H bonds
Bonds formed: 1 mol of H-Cl bonds, 1 mol of C-Cl bonds
D
H = [D(Cl-Cl) + D(C-H)] - [D(H-Cl)+D(C-Cl)][242 kJ + 413 kJ] - [431 kJ + 328 kJ]
-104 kJ
Thus, the reaction is exothermic (because the bonds in the products are stronger than the bonds in the reactants)
Example: The combustion of 1 mol of ethane
bonds broken: 6 moles C-H bonds, 1 mol C-C bonds, 7/2 moles of O=O bonds
bonds formed: 4 moles C=O bonds, 6 moles O-H bonds
D
H = [(6*413) + (348) + (7/2*495)] - [(4*799) + (6*463)]= 4558 - 5974
= -1416 kJ (the reaction is exothermic)
Bond strength and bond length
|
Bond |
Bond Energy (kJ/mol) |
Bond Length (Å) |
|
C-C |
348 |
1.54 |
|
C=C |
614 |
1.34 |
|
C=C |
839 |
1.20 |
As the number of bonds between two atoms increases, the bond grows shorter and stronger
1996 Michael Blaber