Basic Concepts of Chemical Bonding

Types of Chemical Bonds

Ionic Bonding

The electrostatic attraction of closely packed, oppositely charged ions (typical between metals and nonmetals)

Covalent Bond

Exist where electrons are shared between nuclei (typical between nonmetal atoms)

The electron density is located primarily between the two nuclei

Metallic Bonds

Metallic bonds consist of atoms bonded to several neighboring atoms with the electrons free to move among the 3-dimensional structure of the atoms.

Descriptions of Chemical Bonds

Chemical bonds can be described with a variety of properties; this includes bond energy, bond length,

Bond Energy

The energy required to break a bond.

Bond Length

The distance between the nuclei of the bonding atoms. This distance where energy is a minimum between nucleus-nucleus repulsion, electron-electron repulsion, and electron-nucleus attraction.

Octet Rule

Atoms tend to gain, lose, or share electrons until they are surrounded by eight valence electrons. This consists of a full s and p sublevels.

Atoms near Helium will attain only 2 valence electrons, a full s sublevel.

Lewis Symbols

A Lewis symbol shows the symbol of an atom or atoms in a compound with dots representing each valence electron. For a single atom, there is a maximum of eight dots around the atom, and we limit the representation to a maximum of two dots per side (top, bottom, left, right)

Ionic Bonds

Ionic Compound

A compound formed from a positive cation and a negative anion. A metal reacts with nonmetal forms an ionic compound.

Ionic compounds are often brittle, crystalline (highly structured forming flat surfaces and clear edges), high melting points and high boiling points.

Lattice Energy

The strength of the ionic bonding of a solid ionic compound is given by the lattice energy, which is the energy required to completely separate a mole of an ionic solid into its gaseous ions.

MX(s) à M+(g) + X-(g)

This energy value will be positive since the process is an endothermic process.

All binary ionic compounds formed by an alkali metal and a halogen (except for cesium salts) have the same structure as sodium chloride where each atom is surrounded by six ions of the opposite charge.

Lattice energy can be represented by a modified form of Coulomb's law:

Lattice energy = k(Q1Q2/r)

where k depends on the structure of the solid and the electron configurations of the ions,
r is the distance between ion centers; and Q1 and Q2 are the numerical ion charges

The lattice energy increases as the charges on the ions increase and as the radii decrease.

Since energy is a state function, this energy value can be calculated from a series of other reaction steps.

Energy Calculations by Adding Reactions

Since energy is a state function, the energy value of a reaction can be calculated from the sum of other reactions.

Some Rules for adding Reactions:

·        A compound showing up as both a reactant and product can be cancelled out of the reaction.

·        Reversing the reaction changes the sign of the energy.

·        Multiplying the reaction multiplies the energy.

Lattice energy is equal to the sum of the ionization energy of the metal, the electron affinity of the nonmetal, the sublimation energy of the metal, and the bond energy of the diatomic halogen minus the energy of formation of the ionic compound.

Example:

Mg(s) à Mg(g)                         DH = 150 kJ                        Sublimation
Mg(g) à Mg2+(g) + 2e-                         DH = 2201 kJ                        Ionization energy (2)
(1/2)O2(g) à O(g)                         DH = 249 kJ                        Bond energy
O(g) + 2e- à O2-(g)                        DH = -337 kJ                        Electron affinities (2)
Minus
Mg(s) + (1/2)O2(g) à MgO(s)                        DH = -601 kJ                        Enthalpy of formation
equal
MgO(s) à Mg2+(g) + O2-(g)                         DH = 2864 kJ                        Lattice energy

Enthalpy of formation is the sum of the ionization energy of the metal, the electron affinity of the nonmetal, the sublimation energy of the metal, the bond energy of the diatomic halogen, and the lattice energy.

Lattice Energies for some Ionic Compounds

Compound

Lattice Energy (kJ/mol)

LiF

1030

LiCl

834

LiI

730

NaF

910

NaCl

788

NaBr

732

NaI

682

KF

808

KCl

701

KBr

671

MgCl2

2326

SrCl2

2127

MgO

2864

CaO

3414

ScN

7547

 

Ions: Electron Configurations and Sizes

In most cases the electron configuration of ions of representative elements match that of a noble gas.

When a nonmetal and a representative-group metal react to form a binary ionic compound, the ions form so that the valence electron configuration of the nonmetal achieves the electron configuration of the next noble gas atom and the valence orbitals of the metal are emptied.

Example: the Neon electron configuration is achieved by O2-, F-, Na+, Mg2+, Al3+

Predicting Formulas of Ionic Compounds

The ionic charges of representative elements will be such to create a noble gas electron configuration.

Several exceptions exist where a second ionic charge is also possible:
Sn (2+, 4+)
Pb (2+, 4+)
Bi (3+, 5+)
Tl (1+, 3+)

Sizes of Ions

Cations are smaller than the parent element

Anions are significantly larger than the parent element

Isoelectronic Ions

In isoelectronic ions, the more protons, the smaller the ion
or the more negative the ion, the larger the ion

Transition Metal Ions

Transition metals have up to 12 electrons beyond a noble gas core. Typically, it is not energetically favorable (higher successive ionization energies) to form ions with high ionic charges. So most transition metals form ions with charges of +1, +2, +3.

In forming ions, electrons are removed first from the level that has the highest value of n. So in forming ions, transition metals loose the valence shell s electrons first before loosing d electrons. This is why most transition metals form a +2 ion along with other charges.

Polyatomic ions

Polyatomic ions are two or more atoms that are covalently bonded together, but have an ionic charge and form ionic bonds with other ions.

Covalent Bonding

Covalent bonds exist where electron pairs are shared between nuclei

The electron density is located primarily between the two nuclei forming an attractive force between the electron pair and each nuclei.

Lewis Structures

In writing Lewis structures, only valence electrons are used.

Rules for Writing Lewis Structures

·        Sum the valence electrons for all the atoms

·        Write the symbols of the atoms in the appropriate layout.

·        Connect the bonding atoms with a single line (representing a pair, 2, of electrons)

·        Arrange the remaining electrons to satisfy the duet rule for hydrogen and octet rule for the remaining elements.

·        Any excess electrons go on the central atom (if period 3 element or higher) even if the octet is exceeded.

·        If octets are not complete, move nonbonding electron pairs into bonds (forming double and triple bonds) until octets are complete

Duet Rule

Hydrogen forms stable molecules when it shares two electrons

Octet Rule

Second row elements form stable molecules when its orbital has 8 electrons.

Comments/Exceptions to the Octet Rule

·        The second row elements, C, N, O, F should always be assumed to obey the octet rule

·        The second-row elements, B and Be often have fewer than eight electrons around them. These compounds are very reactive

·        The second-row elements never exceed the octet rule

·        Third row and heavier elements often satisfy the octet rule, but can exceed it using the d subshell (Example: SF6 forms 6 bonds around sulfur using 12 electrons)

·        When writing the Lewis structure, satisfy the octet rule first, additional electrons are placed on elements with available d subshells.

Single Bond

The sharing of one pair of electrons.

A C-C single bond is typically 1.54°A in length.

Double Bond

The sharing of two pairs of electrons.

A C-C double bond is typically 1.34°A in length.

Triple Bond

The sharing of three pairs of electrons

A C-C triple bond is typically 1.20°A in length.

Average Bond Lengths

Bond lengths shorten as the number of shared electrons increases

Resonance

Resonance occurs when more than one valid Lewis structure can be written for particular molecule. The actual structure is the average of the resonance structures.

Electrons are delocalized and can move around the entire molecule.

Examples: NO3-, SO3, SO2

Resonance in Benzene

Benzene, C6H6, is a cyclic organic hydrocarbon molecule that shows resonance that is typical of aromatic organic molecules.

The Lewis structure of benzene will have three C-C double bonds and three C-C single bonds. There are two equivalent Lewis structures with the double and single bonds switched.

The molecule actually has 6 identical bonds with a bond length that is intermediate (1.40°A) between single bonds (1.54 °A) and double bonds (1.34 °A).

The structure can be drawn with three double bonds or with a circle inside the six single bonds, representing the delocalized double bonds.

Formal Charge

Molecules or polyatomic ions that can exceed the octet rule often have many nonequivalent Lewis structures

A charge estimation method will help determine which is the best Lewis structure.

Formal charge is the difference between the number of valence electrons on the free atom and the number of valence electrons assigned to the atom in the molecule.

Formal charge = Valence electrons – Assigned electrons

Rules Governing Formal Charge

·        Sum lone pair electrons and one-half the shared electrons to get the assigned electrons

·        Subtract the number of assigned electrons from the number of valence electrons of the neutral atom to get the formal charge

·        The sum of the formal charges of all atoms in a given molecule or ion must equal the overall charge of the species

·        If nonequivalent Lewis structures exist for a species, those with formal charges closest to zero are better.

·        Lewis Structures with any negative formal charges are expected to have these charges reside on the most electronegative atoms

Example: BF3

Structure with three single bonds and 6 valence electrons on B

F: Formal charge = 7 Valence electrons – 7 assigned electrons = 0

B: Formal charge = 3 valence electrons – 3 assigned electrons = 0

Three resonance structures with one double bond and 8 valence electrons on B

F (single bond): Formal charge = 7 Valence electrons – 7 assigned electrons = 0

F (double bond): Formal charge = 7 Valence electrons – 6 assigned electrons = 1

B: Formal charge = 3 valence electrons – 4 assigned electrons = -1

The single bond BF3 is the better structure since the formal charges are both zero. also on the double bonded BF3 the negative formal charge is on the more electropositive element.

Nonpolar Covalent Bond

Occurs when electrons are shared equally between nuclei.

Polar Covalent Bond

Occurs when electrons are shared unequally between nuclei.

Electronegativity

The ability of an atom in a molecule to attract shared electrons to itself.

Electronegativity values generally increase from left to right across the periodic table (except noble gases) and increase up a group.

The high value is 4.0 for fluorine and the low value is 0.7 for Francium.

Electronegativity is calculated using Linus Pauling's method. This consists of calculating an expected bond energy for H-X  = (H-H bond energy + X-X bond energy)/2
which is the average bond energy between H-H and X-X
and comparing this average value with the measured value, D = (H-X)measured – (H-X)theor

A large D represents a large polarity

Electronegativities of the Elements

H

2

 

 

 

 

 

 

 

 

 

 

13

14

15

16

17

He

2.1

IIA

 

 

 

 

 

 

 

 

 

 

IIIA

IVA

VA

VIA

VIIA

-

Li

Be

 

 

 

 

 

 

 

 

 

 

B

C

N

O

F

Ne

1.0

1.5

 

 

 

 

 

 

 

 

 

 

2.0

2.5

3.0

3.5

4.0

-

Na

Mg

3

4

5

6

7

8

9

10

11

12

Al

Si

P

S

Cl

Ar

0.9

1.2

IIIB

IVB

VB

VIB

VIIB

VIIIB

VIIIB

VIIIB

IB

IIB

1.5

1.8

2.1

2.5

3.0

-

K

Ca

Sc

Ti

V

Cr

Mn

Fe

Co

Ni

Cu

Zn

Ga

Ge

As

Se

Br

Kr

0.8

1.0

1.3

1.5

1.6

1.6

1.5

1.8

1.8

1.8

1.9

1.6

1.6

1.8

2.0

2.4

2.8

-

Rb

Sr

Y

Zr

Nb

Mo

Tc

Ru

Rh

Pd

Ag

Cd

In

Sn

Sb

Te

I

Xe

0.8

1.0

1.2

1.4

1.6

1.8

1.9

2.2

2.2

2.2

1.9

1.7

1.7

1.8

1.9

2.1

2.5

-

Cs

Ba

La

Hf

Ta

W

Re

Os

Ir

Pt

Au

Hg

Tl

Pb

Bi

Po

At

Rn

0.7

0.9

1.0

1.3

1.5

1.7

1.9

2.2

2.2

2.2

2.4

1.9

1.8

1.8

1.9

2.0

2.2

-

 

Electronegativity and Bond Polarities

Bonds containing a difference in electronegativity of less than 0.4 are normally considered to be nonpolar. Covalent bonds containing a difference in electronegativity between the atoms of 0.4 or more are typically considered polar.

Bond Polarity and Dipole Moments

Dipolar/Dipole Moment

A molecule that has a center of positive charge that is separate from the center of negative charge

The dipole is often shown using an arrow pointing to the negative charge. Or by using d+ and d-  

Bond Polarity and Dipole Moment

Any diatomic molecule with a polar bond has a dipole moment.

Polyatomic molecules that have polar bonds will have a dipole moment unless the symmetry of the molecule cancels out the effects of the polar bonds.

The polar bonds usually only cancel out on totally symmetric molecules such as tetrahedral molecules with four identical bonds (CCl4), or trigonal planar molecules (SO3) with three identical bonds or linear molecules with two identical bonds (CO2).

Dipole moments are often reported in debyes (D).

1 D = 3.34 x 10-30 coulomb-meter (C-m)

We often measure charge in units of electronic charge, e (1.60 x 10-19C) and distance in angstroms.

Suppose that two charges +0.5 and –0.5 (in units of e) are separated by 1.00 °A. The dipole moment produced is:

m = Qr = (1/2)(1.60 x 10-19C)(1.00 °A)(10-10 m/°A(1D/3.34 x 10-30 C-m) = 2.39 D

Blending of Ionic and Covalent Character

There is a gradient between polar covalent bonds and ionic bonds that is not always clearly distinguishable.

This is seen in naming conventions and chemical properties.

Naming Conventions

Ionic                             Molecular
CaC2                  Calcium carbide                  CO2                  Carbon dioxide
Fe2O3                  Iron (III) oxide                  Cl2O3                  Dichlorine trioxide
K2O                  Potassium oxide                  H2S                  Dihydrogen sulfide

Ionic                             Common Crossover names
TiO2                  Titanium (IV) oxide                  Titanium dioxide
                                    (white solid)
SnCl4         Tin (IV) chloride                  Tin tetrachloride
                                    (colorless liquid, mp = -33°C)
Mn2O7                  Manganese (VII) oxide                  Dimanganese heptoxide
                                    (green liquid, mp = 5.9°C)

Many compounds of metals with high oxidation numbers have properties more similar to molecular compounds.

 

Bond Enthalpy

Bond enthalpy is the enthalpy change (DH) for the breaking of a particular bond in one mole of a substance in the gas phase.

Bond enthalpy is always a positive quantity.

We can sue the notation D(bond type) to label bond enthalpies.
Example: D(C-H) = 413 kJ/mol.

Average Bond Enthalpies (kJ/mol)

Single Bonds

C-H     413

N-H     391

O-H     463

F-F      155

C-C     348

N-N     163

O-O     146

 

C-N     293

N-O     201

O-F     190

Cl-F     253

C-O     358

N-F     272

O-Cl    203

Cl-Cl    242

C-F      485

N-Cl    200

O-I      234

 

C-Cl    328

N-Br    243

 

Br-F     237

C-Br    276

 

S-H      339

Br-Cl   218

C-I       240

H-H     436

S-F      327

Br-Br   193

C-S      259

H-F      567

S-Cl     253

 

 

H-Cl    431

S-Br     218

I-Cl      208

Si-H     323

H-Br    366

S-S      266

I-Br      175

Si-Si     226

H-I       299

 

I-I        151

Si-C     301

 

 

 

Si-O     368

 

 

 

Si-Cl    464

 

 

 

Multiple Bonds

C=C    614

N=N    418

O=O    495

 

C=C    839

N=N    941

 

 

C=N    615

N=O    607

S=O     523

 

C=N    891

 

S=S     418

 

C=O    799

 

 

 

C=O    1072

 

 

 

 

Bond Energy and Enthalpies of Reaction

The enthalpy of a reaction will be the sum of bond energies of bonds broken (endothermic) minus the sum of bond energies of bonds formed (exothermic)

DH = S(bonds broken) – S(bonds formed)

for the reaction

H2 + Cl2 à 2HCl

DHrxn = 432 kJ/mol H2 + 239 kJ/mol Cl2 – 2(427 kJ/mol HCl)
= -183 kJ (for reaction as written)
or for HCl
DH(HCl) = -183/2  = -92 kJ/mol HCl

H2 (g) + I2 (g) ßà 2HI (g)

DHrxn = 432 kJ/mol H2 + 149 kJ/mol I2 – 2(295 kJ/mol HI) = -9 kJ
or for HI
DH(HI) = -9/2  = -4 kJ/mol

Multiple Bonds

In general, as the number of bonds between two atoms increases, the bond grows shorter and stronger.

Average Bond Lengths for some Bonds

Bond

Bond Length (°A)

Bond

Bond Length (°A)

C-C

1.54

N-N

1.47

C=C

1.34

N=N

1.24

C=C

1.20

N=N

1.10

C-N

1.43

N-O

1.36

C=N

1.38

N=O

1.22

C=N

1.16

 

 

 

 

O-O

1.48

C-O

1.43

O=O

1.21

C=O

1.23

 

 

C=O

1.13

 

 

Covalent Bond Energies and Chemical Reactions

The energy of a particular type of bond (i.e. a C-H bond) varies with the local environment; however, the concept of a bond energy is still useful.

i.e. Methane can be considered to have four C-H bonds

Stabilizing energy of methane  = 4 (C-H bonds) = 4(413 kJ/mol) = 1652 kJ/mol

Odd-Electron Molecules

Some molecules formed from nonmetals contain odd numbers of electrons (NO, NO2)

The formal charge model works better for determining the arrangement of odd electron molecules.