Salts are characterized by having more than one component, most commonly with one or more cationic components accompanied by one or more anionic component. Although such components are physically associated by ionic bonds, they are traditionally depicted on paper as separate, disjoint fragments. So, in addition to all the issues involved with drawing each individual fragment, salts must also be drawn with a consideration of how those fragments should be oriented in relation to each other.
It should be noted that although salts consist of cationic and anionic components, they are not always drawn with explicit charges. Many pharmaceutical compounds, for example, are isolated as hydrochloride salts. It is often reasonable -- and, when the site of protonation is variable or uncertain, unavoidable -- to draw such compounds with a neutral parent structure and a neutral hydrochloric acid.
Some compounds may be formally drawn with positive and negative charges within a single structural fragment. Compounds with an anionic center directly adjacent to a cationic center are termed ylides. In other cases where the charges balance to create a compound that is neutral overall, such a compound is termed a zwitterion. Athough such compunds may in some cases be considered salts -- Chemical Abstracts Service uses the term "inner salt" to name zwitterions -- the discussion here is limited to salts that are or could be depicted using multiple fragments.
Structures that are known to be ionic should be depicted as such. They should be drawn with atoms bearing explicit positive and negative charges, and there should be a space (rather than a bond) between those atoms.
| RECOMMENDED | RECOMMENDED | AVOID | AVOID | AVOID |
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Two-component salts should be drawn with the cation on the left and the anion on the right
| RECOMMENDED | RECOMMENDED | AVOID | AVOID |
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In salts where one component is significantly larger than the other (including most metal salts of organic acids), it is also acceptable to position the smaller fragment near the oppositely-charged site in the larger fragment, with the positioning of the larger fragment determined by other considerations.
| RECOMMENDED | RECOMMENDED |
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The fragments should be positioned as if there were a single bond between the cationic and anionic centers, even if this requires that the cation be drawn on the right side of the anion. Usually this will dictate the positioning of the smaller fragment, according to other recommendations (that straight changes not have arbitrary bends in them, for example).
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This sort of positioning should not be attempted when one of the ionic centers has enough other substituents as to make the resulting diagram too crowded.
[examples - hexafluorophosphate]
These recommendations extend to organic salts as well as inorganic ones
[need examples]
Unlike with two-component salts, multiple-component salts should generally not be written as separate components in a linear arrangement, since that may imply a physical ordering that is not present. Instead, most multiple-component salts should be indicated using formulas (according to the guidelines of the [new Red Book -- need reference])
| RECOMMENDED | AVOID |
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In simple cases, it may be possible to draw a multiple-component salt in a pseudo-structural manner. This is generally limited to cases where the the salt contains exactly one cation or exactly one anion, with the multiple anions arranged symmetrically around the one cation (for example).
| RECOMMENDED | RECOMMENDED | RECOMMENDED |
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In addition to the styles discussed above, it is also acceptable to depict the ions in structural form, but without any implied association between the ions. This is the preferred form for mixed salts where there is more than one positively charged atoms and more than one negatively charged atom, and where the association between the various cationic and anionic centers simply isn't known. In this style, the largest ion(s) should be enclosed in brackets, to emphasize that there is no structural association between them and the other ion(s). The selection of ions to bracket is performed solely based on size, and so the bracketed ion(s) may be positively or negatively charged. The bracketed ions are then placed on the left, and the other ions are placed on the right. If an ion appears more than once, it may be depicted a single time, with an additional numeral present to indicate the repeat count. If the repeated ion is represented by a formula, the repeat count should be placed to the left of the formula in regular-style (non-superscripted, non-subscripted text) and separated from the formula by a space. If the repeated ion is represented in structural form, it must be enclosed in brackets, and the repeat count should be positioned as a subscript toward the bottom-right of the rightmost bracket. The various ions should be clearly separated from each other, but not separated so widely as to seem wholly unrelated. For most purposes a separation distance roughly equivalent to the structure's average bond length is usually reasonable.
| RECOMMENDED | RECOMMENDED | RECOMMENDED |
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"Partial" or "acidic" salts would be best drawn in a similar manner: [Keith says: The pyridine-2,3-dicarboxylic acid example is a challenge. I do not think that chemists will be happy to adopt the fully ionized form that is recommended. The acid isn't strong enough to be fully ionized. But how else should it be represented? That's a challenge and I cannot think of a better way. The most acidic proton can be removed but often that is based on an inspired guess.]
| RECOMMENDED | AVOID | AVOID | AVOID |
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.Na(-H) |
Salts drawn as multiple neutral components (such as hydrochlorides) should not have the larger structure enclosed in brackets. The larger structures are drawn to the left, and the smaller ones to the right, with a reasonable separation as discussed above. It is acceptable (but not required) to precede small neutral components by a center-dot if those components are represented as formulas. The center-dot, if present, should be separated from the formula by a space. If a repeat count is required as well as a center-dot, the center-dot should not be separated from the repeat count, but the repeat count should still be separated from the rest of the formula by a space.
| RECOMMENDED | RECOMMENDED |
 [Display specific stereoisomer] |
 [Display specific stereoisomer] |
