Instead, we use the concept of resonance: if two or more Lewis structures with the same arrangement of atoms can be written for a molecule or ion, the actual distribution of electrons is an average of that shown by the various Lewis structures. It is not possible to write a single Lewis structure for NO 2 − NO 2 − in which nitrogen has an octet and both bonds are equivalent. Experiments show, however, that both N–O bonds in NO 2 − NO 2 − have the same strength and length, and are identical in all other properties. A double bond between two atoms is shorter (and stronger) than a single bond between the same two atoms. If nitrite ions do indeed contain a single and a double bond, we would expect for the two bond lengths to be different. The electrons involved in the N–O double bond, however, are in different positions: You may have noticed that the nitrite anion in Example 7.8 can have two possible structures with the atoms in the same positions. Also, it places the least electronegative atom in the center, and the negative charge on the more electronegative element (Guideline 4). However, the first arrangement of atoms is preferred because it has the lowest number of atoms with nonzero formal charges (Guideline 2). Note that the sum of the formal charges in each case is equal to the charge of the ion (–1). Possible Lewis structures and the formal charges for each of the three possible structures for the thiocyanate ion are shown here: The formal charges present in each of these molecular structures can help us pick the most likely arrangement of atoms. We can draw three possibilities for the structure: carbon in the center and double bonds, carbon in the center with a single and triple bond, and oxygen in the center with double bonds:Ĭomparing the three formal charges, we can definitively identify the structure on the left as preferable because it has only formal charges of zero (Guideline 1).Īs another example, the thiocyanate ion, an ion formed from a carbon atom, a nitrogen atom, and a sulfur atom, could have three different molecular structures: CNS –, NCS –, or CSN –. We know from our previous discussion that the less electronegative atom typically occupies the central position, but formal charges allow us to understand why this occurs. To see how these guidelines apply, let us consider some possible structures for carbon dioxide, CO 2. When we must choose among several Lewis structures with similar distributions of formal charges, the structure with the negative formal charges on the more electronegative atoms is preferable.Lewis structures are preferable when adjacent formal charges are zero or of the opposite sign.If the Lewis structure must have nonzero formal charges, the arrangement with the smallest nonzero formal charges is preferable.A molecular structure in which all formal charges are zero is preferable to one in which some formal charges are not zero.A few guidelines involving formal charge can be helpful in deciding which of the possible structures is most likely for a particular molecule or ion: In many cases, following the steps for writing Lewis structures may lead to more than one possible molecular structure-different multiple bond and lone-pair electron placements or different arrangements of atoms, for instance. The arrangement of atoms in a molecule or ion is called its molecular structure. N: 0 all three Cl atoms: 0 Using Formal Charge to Predict Molecular Structure Thus, we calculate formal charge as follows: Another way of saying this is that formal charge results when we take the number of valence electrons of a neutral atom, subtract the nonbonding electrons, and then subtract the number of bonds connected to that atom in the Lewis structure. The formal charge of an atom in a molecule is the hypothetical charge the atom would have if we could redistribute the electrons in the bonds evenly between the atoms. We can use the concept of formal charges to help us predict the most appropriate Lewis structure when more than one is reasonable. As we have seen, however, in some cases, there is seemingly more than one valid structure for a molecule. In the previous section, we discussed how to write Lewis structures for molecules and polyatomic ions. Explain the concept of resonance and draw Lewis structures representing resonance forms for a given molecule.Use formal charges to identify the most reasonable Lewis structure for a given molecule.Compute formal charges for atoms in any Lewis structure.Learning Objectives By the end of this section, you will be able to:
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