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Using Lewis Dot Symbols to Describe Covalent Bonding
This sharing of electrons allowing atoms to "stick" together is the basis of covalent bonding. There is some intermediate distant, generally a bit longer than 0.1 nm, or if you prefer 100 pm, at which the attractive forces significantly outweigh the repulsive forces and a bond will be formed if both atoms can achieve a completen s2np6 configuration. It is this behavior that Lewis captured in his octet rule. The valence electron configurations of the constituent atoms of a covalent compound are important factors in determining its structure, stoichiometry, and properties. For example, chlorine, with seven valence electrons, is one electron short of an octet. If two chlorine atoms share their unpaired electrons by making a covalent bond and forming Cl2, they can each complete their valence shell:
Each chlorine atom now has an octet. The electron pair being shared by the atoms is called a bonding pair ; the other three pairs of electrons on each chlorine atom are called lone pairs. Lone pairs are not involved in covalent bonding. If both electrons in a covalent bond come from the same atom, the bond is called a coordinate covalent bond.
We can illustrate the formation of a water molecule from two hydrogen atoms and an oxygen atom using Lewis dot symbols:
The structure on the right is the Lewis electron structure, or Lewis structure, for H2O. With two bonding pairs and two lone pairs, the oxygen atom has now completed its octet. Moreover, by sharing a bonding pair with oxygen, each hydrogen atom now has a full valence shell of two electrons. Chemists usually indicate a bonding pair by a single line, as shown here for our two examples:
The following procedure can be used to construct Lewis electron structures for more complex molecules and ions:
1. Arrange the atoms to show specific connections. When there is a central atom, it is usually the least electronegative element in the compound. Chemists usually list this central atom first in the chemical formula (as in CCl4 and CO32−, which both have C as the central atom), which is another clue to the compound’s structure. Hydrogen and the halogens are almost always connected to only one other atom, so they are usually terminal rather than central.
Note the Pattern
The central atom is usually the least electronegative element in the molecule or ion; hydrogen and the halogens are usually terminal.
2. Determine the total number of valence electrons in the molecule or ion. Add together the valence electrons from each atom. (Recall from Chapter 2 that the number of valence electrons is indicated by the position of the element in the periodic table.) If the species is a polyatomic ion, remember to add or subtract the number of electrons necessary to give the total charge on the ion. For CO32−, for example, we add two electrons to the total because of the −2 charge.
3. Place a bonding pair of electrons between each pair of adjacent atoms to give a single bond. In H2O, for example, there is a bonding pair of electrons between oxygen and each hydrogen.
4. Beginning with the terminal atoms, add enough electrons to each atom to give each atom an octet (two for hydrogen). These electrons will usually be lone pairs.
5. If any electrons are left over, place them on the central atom. We explain in Section 4.6 that some atoms are able to accommodate more than eight electrons.
6. If the central atom has fewer electrons than an octet, use lone pairs from terminal atoms to form multiple (double or triple) bonds to the central atom to achieve an octet. This will not change the number of electrons on the terminal atoms.
Now let’s apply this procedure to some particular compounds, beginning with one we have already discussed.
H2O
1. Because H atoms are almost always terminal, the arrangement within the molecule must be HOH.
2. Each H atom (group 1) has 1 valence electron, and the O atom (group 16) has 6 valence electrons, for a total of 8 valence electrons.
3. Placing one bonding pair of electrons between the O atom and each H atom gives H:O:H, with 4 electrons left over.
4. Each H atom has a full valence shell of 2 electrons.
5. Adding the remaining 4 electrons to the oxygen (as two lone pairs) gives the following structure:
This is the Lewis structure we drew earlier. Because it gives oxygen an octet and each hydrogen two electrons, we do not need to use step 6.
OCl−
1. With only two atoms in the molecule, there is no central atom.
2. Oxygen (group 16) has 6 valence electrons, and chlorine (group 17) has 7 valence electrons; we must add one more for the negative charge on the ion, giving a total of 14 valence electrons.
3. Placing a bonding pair of electrons between O and Cl gives O:Cl, with 12 electrons left over.
4. If we place six electrons (as three lone pairs) on each atom, we obtain the following structure:
Each atom now has an octet of electrons, so steps 5 and 6 are not needed. The Lewis electron structure is drawn within brackets as is customary for an ion, with the overall charge indicated outside the brackets, and the bonding pair of electrons is indicated by a solid line. OCl− is the hypochlorite ion, the active ingredient in chlorine laundry bleach and swimming pool disinfectant.
CH2O
1. Because carbon is less electronegative than oxygen and hydrogen is normally terminal, C must be the central atom. One possible arrangement is as follows:
2. Each hydrogen atom (group 1) has one valence electron, carbon (group 14) has 4 valence electrons, and oxygen (group 16) has 6 valence electrons, for a total of [(2)(1) + 4 + 6] = 12 valence electrons.
3. Placing a bonding pair of electrons between each pair of bonded atoms gives the following:
Six electrons are used, and 6 are left over.
4. Adding all 6 remaining electrons to oxygen (as three lone pairs) gives the following:
Although oxygen now has an octet and each hydrogen has 2 electrons, carbon has only 6 electrons.
5. There are no electrons left to place on the central atom.
6. To give carbon an octet of electrons, we use one of the lone pairs of electrons on oxygen to form a carbon–oxygen double bond:
Both the oxygen and the carbon now have an octet of electrons, so this is an acceptable Lewis electron structure. The O has two bonding pairs and two lone pairs, and C has four bonding pairs. This is the structure of formaldehyde, which is used in embalming fluid.
An alternative structure can be drawn with one H bonded to O. Formal charges, discussed later in this section, suggest that such a structure is less stable than that shown previously.
Example
Write the Lewis electron structure for each species.
- NCl3
- S2−
- NOCl
Given: chemical species
Asked for: Lewis electron structures
Strategy:
Use the six-step procedure to write the Lewis electron structure for each species.
Solution:
-
Nitrogen is less electronegative than chlorine, and halogen atoms are usually terminal, so nitrogen is the central atom. The nitrogen atom (group 15) has 5 valence electrons and each chlorine atom (group 17) has 7 valence electrons, for a total of 26 valence electrons. Using 2 electrons for each N–Cl bond and adding three lone pairs to each Cl account for (3 × 2) + (3 × 2 × 3) = 24 electrons. Rule 5 leads us to place the remaining 2 electrons on the central N:
Nitrogen trichloride is an unstable oily liquid once used to bleach flour; this use is now prohibited in the United States.
-
In a diatomic molecule or ion, we do not need to worry about a central atom. Each sulfur atom (group 16) contains 6 valence electrons, and we need to add 2 electrons for the −2 charge, giving a total of 14 valence electrons. Using 2 electrons for the S–S bond, we arrange the remaining 12 electrons as three lone pairs on each sulfur, giving each S atom an octet of electrons:
-
Because nitrogen is less electronegative than oxygen or chlorine, it is the central atom. The N atom (group 15) has 5 valence electrons, the O atom (group 16) has 6 valence electrons, and the Cl atom (group 17) has 7 valence electrons, giving a total of 18 valence electrons. Placing one bonding pair of electrons between each pair of bonded atoms uses 4 electrons and gives the following:
Adding three lone pairs each to oxygen and to chlorine uses 12 more electrons, leaving 2 electrons to place as a lone pair on nitrogen:
Because this Lewis structure has only 6 electrons around the central nitrogen, a lone pair of electrons on a terminal atom must be used to form a bonding pair. We could use a lone pair on either O or Cl. Because we have seen many structures in which O forms a double bond but none with a double bond to Cl, it is reasonable to select a lone pair from O to give the following:
All atoms now have octet configurations. This is the Lewis electron structure of nitrosyl chloride, a highly corrosive, reddish-orange gas.
Exercise
Write Lewis electron structures for CO2 and SCl2, a vile-smelling, unstable red liquid that is used in the manufacture of rubber.
Answer:
Formal Charges
It is sometimes possible to write more than one Lewis structure for a substance that does not violate the octet rule, as we saw for CH2O, but not every Lewis structure may be equally reasonable. In these situations, we can choose the most stable Lewis structure by considering the formal charge on the atoms, which is the difference between the number of valence electrons in the free atom and the number assigned to it in the Lewis electron structure. The formal charge is a way of computing the charge distribution within a Lewis structure; the sum of the formal charges on the atoms within a molecule or an ion must equal the overall charge on the molecule or ion. A formal charge does not represent a true charge on an atom in a covalent bond but is simply used to predict the most likely structure when a compound has more than one valid Lewis structure.
To calculate formal charges, we assign electrons in the molecule to individual atoms according to these rules:
- Nonbonding electrons are assigned to the atom on which they are located.
- Bonding electrons are divided equally between the bonded atoms.
For each atom, we then compute a formal charge:
To illustrate this method, let’s calculate the formal charge on the atoms in ammonia (NH3) whose Lewis electron structure is as follows:
A neutral nitrogen atom has five valence electrons (it is in group 15). From its Lewis electron structure, the nitrogen atom in ammonia has one lone pair and shares three bonding pairs with hydrogen atoms, so nitrogen itself is assigned a total of five electrons [2 nonbonding e− + (6 bonding e−/2)]. Substituting into Equation 5.3.1, we obtain
A neutral hydrogen atom has one valence electron. Each hydrogen atom in the molecule shares one pair of bonding electrons and is therefore assigned one electron [0 nonbonding e− + (2 bonding e−/2)]. Using Equation 4.4.1 to calculate the formal charge on hydrogen, we obtain
The hydrogen atoms in ammonia have the same number of electrons as neutral hydrogen atoms, and so their formal charge is also zero. Adding together the formal charges should give us the overall charge on the molecule or ion. In this example, the nitrogen and each hydrogen has a formal charge of zero. When summed the overall charge is zero, which is consistent with the overall charge on the NH3 molecule.
Typically, the structure with the most charges on the atoms closest to zero is the more stable Lewis structure. In cases where there are positive or negative formal charges on various atoms, stable structures generally have negative formal charges on the more electronegative atoms and positive formal charges on the less electronegative atoms. The next example further demonstrates how to calculate formal charges.
Example
Calculate the formal charges on each atom in the NH4+ ion.
Given: chemical species
Asked for: formal charges
Strategy:
Identify the number of valence electrons in each atom in the NH4+ ion. Use the Lewis electron structure of NH4+ to identify the number of bonding and nonbonding electrons associated with each atom and then use Equation 4.4.1 to calculate the formal charge on each atom.
Solution:
The Lewis electron structure for the NH4+ion is as follows:
The nitrogen atom shares four bonding pairs of electrons, and a neutral nitrogen atom has five valence electrons. Using Equation 4.4.1, the formal charge on the nitrogen atom is therefore
Each hydrogen atom in has one bonding pair. The formal charge on each hydrogen atom is therefore
The formal charges on the atoms in the NH4+ ion are thus
Adding together the formal charges on the atoms should give us the total charge on the molecule or ion. In this case, the sum of the formal charges is 0 + 1 + 0 + 0 + 0 = +1.
Exercise
Write the formal charges on all atoms in BH4-
Answer:
If an atom in a molecule or ion has the number of bonds that is typical for that atom (e.g., four bonds for carbon), its formal charge is zero.
Using Formal Charges to Distinguish between Lewis Structures
As an example of how formal charges can be used to determine the most stable Lewis structure for a substance, we can compare two possible structures for CO2. Both structures conform to the rules for Lewis electron structures.
CO2
1. C is less electronegative than O, so it is the central atom.
2. C has 4 valence electrons and each O has 6 valence electrons, for a total of 16 valence electrons.
3. Placing one electron pair between the C and each O gives O–C–O, with 12 electrons left over.
4. Dividing the remaining electrons between the O atoms gives three lone pairs on each atom:
This structure has an octet of electrons around each O atom but only 4 electrons around the C atom.
5. No electrons are left for the central atom.
6. To give the carbon atom an octet of electrons, we can convert two of the lone pairs on the oxygen atoms to bonding electron pairs. There are, however, two ways to do this. We can either take one electron pair from each oxygen to form a symmetrical structure or take both electron pairs from a single oxygen atom to give an asymmetrical structure:
Both Lewis electron structures give all three atoms an octet. How do we decide between these two possibilities? The formal charges for the two Lewis electron structures of CO2 are as follows:
Both Lewis structures have a net formal charge of zero, but the structure on the right has a +1 charge on the more electronegative atom (O). Thus the symmetrical Lewis structure on the left is predicted to be more stable, and it is, in fact, the structure observed experimentally. Remember, though, that formal charges do not represent the actual charges on atoms in a molecule or ion. They are used simply as a bookkeeping method for predicting the most stable Lewis structure for a compound.
Note the Pattern
The Lewis structure with the set of formal charges closest to zero is usually the most stable
Example
The thiocyanate ion (SCN−), which is used in printing and as a corrosion inhibitor against acidic gases, has at least two possible Lewis electron structures. Draw two possible structures, assign formal charges on all atoms in both, and decide which is the preferred arrangement of electrons.
Given: chemical species
Asked for: Lewis electron structures, formal charges, and preferred arrangement
Strategy:
A Use the step-by-step procedure to write two plausible Lewis electron structures for SCN−.
B Calculate the formal charge on each atom using Equation 4.4.1.
C Predict which structure is preferred based on the formal charge on each atom and its electronegativity relative to the other atoms present.
Solution:
A Possible Lewis structures for the SCN− ion are as follows:
B We must calculate the formal charges on each atom to identify the more stable structure. If we begin with carbon, we notice that the carbon atom in each of these structures shares four bonding pairs, the number of bonds typical for carbon, so it has a formal charge of zero. Continuing with sulfur, we observe that in (a) the sulfur atom shares one bonding pair and has three lone pairs and has a total of six valence electrons. The formal charge on the sulfur atom is therefore
C Which structure is preferred? Structure (b) is preferred because the negative charge is on the more electronegative atom (N), and it has lower formal charges on each atom as compared to structure (c): 0, −1 versus +1, −2.
Exercise
Salts containing the fulminate ion (CNO−) are used in explosive detonators. Draw three Lewis electron structures for CNO− and use formal charges to predict which is more stable. (Note: N is the central atom.)
Answer:
The second structure is predicted to be more stable.
Contributors
- Anonymous
FAQs
What is 1.3 chemical bonding? ›
1 What is Chemical Bonding? Chemical Bonding refers to the formation of a chemical bond between two or more atoms, molecules, or ions to give rise to a chemical compound. These chemical bonds are what keep the atoms together in the resulting compound.
What is Lewis dot structure of pc13? ›PCl3 (Phosphorus Trichloride) Lewis Structure. Phosphorus trichloride (PCl3) contains three chlorine atoms and one phosphorus atoms. In PCl3 lewis structure, each chlorine atom is joint with center phosphorus atom through a single bond. Also, there is a lone pair on phosphorus atom.
What is the bond order for NO − 3? ›Answer and Explanation: The bond order for NO3 -1 (nitrate) is 1.33.
Is PCl3 an octet? ›In PCl3, the octet for both phosphorus and Chlorine atoms is complete. Therefore, it follows the octet rule.
Is 1.8 covalent or ionic? ›The electronegativity difference value is between 0.4 to 1.8 for a polar covalent bond. For example Water, Hydrogen has an electronegativity of 2.1, Oxygen has a 3.5 and the difference is 1.4. The electronegativity difference value is greater than 1.8 for an ionic bond.
Is 3 bonds stronger than 1? ›Are single bonds stronger than triple bonds? Triple bonds are stronger than the equivalent single bonds or double bonds, with a bond order of three.
What shape is PCl3? ›(b) The PCl3 molecule is trigonal pyramidal, while ICl3 is T-shaped.
How many valence electrons does pc13 have? ›Chemical Bonding: PCl3 Lewis Structure
In the PCl3 Lewis structure Phosphorus (P) is the least electronegative so it goes in the center. In the Lewis structure for PCl3 there are a total of 26 valence electrons.
So, the bond order of a nitric oxide molecule is 2.5.
What forms 3 bonds? ›The most common triple bond is in a nitrogen N2 molecule; the second most common is that between two carbon atoms, which can be found in alkynes. Other functional groups containing a triple bond are cyanides and isocyanides. Some diatomic molecules, such as dinitrogen and carbon monoxide, are also triple bonded.
What is the bond order for NO − 2? ›
The bond order of NO2 is 1.5. This can be ve determined by dividing the total number of electron pairs in N-O bonds by the total number of N-O bonds.
Is PCl3 polar or nonpolar bond? ›All the three Chlorine atoms pull the electrons from the phosphorous atom making it a polar molecule.
Does PCl3 have structure? ›PCl3 have pyramidal geometry , where as PCl5 have trigonal bipyramidal shape.
Is PCl3 a Lewis base? ›Answer and Explanation:
The Lewis structure of PCl3 has an electron pair on the phosphorus (P) central atom. This means it is capable of donating an electron pair. Therefore, PCl3 is a Lewis base.
...
| ΔEN | Bonding | Bond Example |
|---|---|---|
| 1.0 - 1.3 | Moderately polar covalent bond | C-O, S-O |
| 1.4 - 1.7 | Highly polar covalent bond | H-O |
| 1.8 - 2.2 | Slightly ionic bond | H-F |
| 2.3 - 3.3 | Highly ionic bond | Na+ F- |
| Electronegativity Difference | Bond Type |
|---|---|
| 0 | nonpolar covalent |
| 0–0.4 | slightly polar covalent |
| 0.5–2.1 | definitely polar covalent |
| >2.1 | likely ionic |
An electronegativity difference greater than 1.7 (1.5 or 2.0 in some texts) leads to ionic bonding. A difference greater than 0.5 (0.2 in some texts) and less than 1.7 (or 1.5 or 2.0) leads to polar covalent bond formation.
Which bond is the hardest? ›In chemistry, a covalent bond is the strongest bond, In such bonding, each of two atoms shares electrons that bind them together. For example - water molecules are bonded together where both hydrogen atoms and oxygen atoms share electrons to form a covalent bond.
What bond is strongest? ›Covalent bonds are the strongest bonds in nature and under normal biological conditions have to be broken with the help of enzymes. This is due to the even sharing of electrons between the bonded atoms and as with anything equally shared there is no conflict to weaken the arrangement.
Which bond is the longest? ›The longest bond is considered to be a carbon-carbon bond, present in diamond. Its length is 154 pm. It is the longest due to the three-dimensional structure of diamond, and the carbon atoms bonded through covalent bonds.
Is I3 nonpolar? ›
However, when we discuss I3- ion, it is a negatively charged ion. Even while drawing its Lewis structure, we do not see any dipole moment of the polar bonds in it, because the overall charge itself is negative on the ion. So, it is neither polar nor nonpolar.
Is I3 planar? ›The lone pairs are present on equatorial axis and two side I atoms are present on axial axis. So, I−3 becomes linear shaped, planar and is non-polar.
Is PCl5 a shape? ›PCl5 has a shape of trigonal bipyramidal whereas IF5 has a shape of square pyramidal, it is due to- Presence of unshared electron pairs on I which is oriented so as to minimise repulsion while in PCl5 has no non-bonding pair. Octet of P is complete whereas that of I is incomplete. No worries!
Which one is not tetrahedral? ›The Complex [Pt(en)2]2+ is not tetrahedral because in this complex the metal ion is Pt which is a present in 5d series and the 5d series element have more diffused orbitals than 3d series elements and hence the ligand have the more closest approach towards metal ion and therefore the complex formed is inner orbital ...
Why is PCl3 pyramidal? ›The other 2 electrons are a lone pair of electrons. PCl3 has a pyramidal shape due to electrons on phosphorous arranged for minimal repulsion/maximal separation hence reducing the repulsion between them.
Can there be 8 valence electrons? ›Referring to the octet rule, atoms attempt to get a noble gas electron configuration, which is eight valence electrons. Sodium has one valence electron, so giving it up would result in the same electron configuration as neon. Chlorine has seven valence electrons, so if it takes one it will have eight (an octet).
How many atoms are in PCl3? ›1 mole of PCl3 contains 4×6.02×1023 atoms. ∴1.4 moles will contain =3.372×1024 atoms.
Can bond order be 1? ›In a covalent bond between two atoms, a single bond has a bond order of one, a double bond has a bond order of two, a triple bond has a bond order of three, and so on.
Does a bond order of 0 exist? ›Electrons will fill according to the energy levels of the orbitals. They will first fill the lower energy orbitals, and then they will fill the higher energy orbitals. If a bond order of zero is obtained, that means that the molecule is too unstable and so it will not exist.
Can bond order be zero? ›A compound with no bond between each other will have a bond order of 0.
Why is water polar? ›
The unequal sharing of electrons between the atoms and the unsymmetrical shape of the molecule means that a water molecule has two poles - a positive charge on the hydrogen pole (side) and a negative charge on the oxygen pole (side). We say that the water molecule is electrically polar.
Why can't oxygen have 4 bonds? ›Oxygen can form only two bonds because it requires two electrons to complete its octet after which it will not have any more vacant orbitals left to accept more electrons and form more bonds.
Can carbon have 5 bonds? ›The number of bonds to carbon cannot exceed four
Carbon has a single 2s orbital and three 2 p orbitals available in its valence shell, and thus can form a maximum of four bonds.
A nitric oxide molecule has a bond order of 2.5.
What is the meaning of 2.5 bond order? ›Only NO has a bond order of 2.5 as per the MO theory. Bond order is a measure of the strength of the bond between the atoms of a molecule. The fact that NO has a bond order of 2.5 means that the bonding in NO is weaker than the N-N bond in N2.
Is a bond order of 2.5 a double bond? ›A single bond has a bond order of 1, a double bond has a bond order of 2, and a triple bond has a bond of 3.
What is a 1.5 bond in chemistry? ›A double bond between two atoms is stronger and shorter than a single bond between the same two atoms. A triple bond is even stronger/shorter. And, you guessed it, a bond order of 1.5 (like in ozone) is stronger than a single bond, but weaker than a double bond.
What is a 1.5 bond? ›A bond order of 1.5 signifies that the Lewis structure of the compound has resonance structures, and that the bonds of the compound will have the characteristics of both a single and double bond.
What are the 3.3 types of chemical bonds? ›- Ionic bonding.
- Covalent bonding.
- Metallic bonding.
Chemical bond is an attraction between atoms that allows the formation of chemical substances. The bond will be formed where attraction forces due to opposite charges were balanced by repulsion forces due to similar charges.
Is 1.5 polar covalent? ›
Polar Covalent Bonds
A bond in which the electronegativity difference between the atoms is between 0.5 and 2.1 is called a polar covalent bond. A polar covalent bond is a covalent bond in which the atoms have an unequal attraction for electrons and so the sharing is unequal.
O2+,N2−,NO+2 are all isoelectronic with 10 bonding electrons and 5 antibonding electrons. So bond order is 2. 5.
Can bond order be less than 1? ›Molecules possessing a bond of order below 1 can be perfectly stable, in the sense that their resulting molecular structure lies in an energetic potential well. Strictly speaking it is enough that at T=0 K and in the absence of any interactions with matter or fields, the molecule will not spontaneously disassemble.
Why does benzene have 1.5 bonds? ›You can think of the bonds as 1.5 bonds (not a single but not a double). A bond is made up of 2 electrons. Each carbon carbon bond has 3 electrons shared (1.5 bonds). Therefore all the bonds are the same length.
What does 5% bond mean? ›The coupon rate is the rate of interest the bond issuer will pay on the face value of the bond, expressed as a percentage.1 For example, a 5% coupon rate means that bondholders will receive 5% x $1,000 face value = $50 every year. Coupon dates are the dates on which the bond issuer will make interest payments.
Which bond is strongest? ›So, in conclusion the ionic bonds are strongest among ionic, covalent and hydrogen bonds.
What are the 3 strongest bonds? ›The three types of chemical bonds in order of weakest to strongest are as follows: ionic bonds, polar covalent bonds, and covalent bonds.
What are the 3.2 types of chemical reactions? ›- 3.2 Types of Reactions.
- Combustion. It is the chemical term for the burning of substances in oxygen to form compounds called oxides. ...
- Synthesis. Naturally occurring elements combine chemically to form compounds. ...
- Decomposition. ...
- Neutralisation. ...
- Precipitation. ...
- Double Displacement. ...
- Oxidation-Reduction.
Therefore, the order from strongest to weakest bond is Ionic bond > Covalent bond > Hydrogen bond > Vander Waals interaction.
What are the 5 chemical bonds? ›The electrical forces, called chemical bonds, can be divided into five types: ionic, covalent, metallic, van der Waals, and hydrogen bonds.
Is water a polar molecule? ›
Water is a Polar Covalent Molecule
The unequal sharing of electrons between the atoms and the unsymmetrical shape of the molecule means that a water molecule has two poles - a positive charge on the hydrogen pole (side) and a negative charge on the oxygen pole (side).
The attraction between individual water molecules creates a bond known as a hydrogen bond.