structural formula

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The structural formula of a chemical compound is a graphical representation of the molecular structure showing how the atoms are arranged. The chemical bonding within the molecule is also shown, either explicitly or implicitly. There are three common representations used in publications, condensed, Lewis type and line-angle formulæ. There are also several formats used for structural representation in chemical databases, such as SMILES, InChI and CML.

Unlike molecular formulae or chemical names, structural formulas provide a representation of the molecular structure. Chemists nearly always describe a chemical reaction or synthesis using structural formulas rather than by chemical names, because the structural formulas allow the chemist to visualize the molecules and the changes that occur.

Many chemical compounds exist in different isomeric forms which have different structures yet the same overall chemical formula. A structural formula indicates the arrangements of atoms in a way that a chemical formula cannot.

Text formulas

In early organic chemistry publications, where use of graphics was severely limited, a text-based system arose to describe organic structures in a line of text. Although this system tends to break down with complex cyclic compounds, it remains a convenient way to represent simple structures

CH₃–CH₂–OH or CH₃CH₂OH

Lewis structures

Lewis structures are flat graphical formulas that show the atom connectivity, but lack information about the three-dimensional structure of molecules. This notation is mostly used for small linear molecules. A single line represents a single bond or single electron pair. Two and three lines represent double and triple bonds, respectively. Alternatively, dots (•) may be used to represent single electrons. Occasionally, this is referred to as a Lewis Dot Structure.

Three-dimensional structures

Several methods exist to picture the the three-dimensional arrangement of atoms in a chiral molecule.

Fischer projection

The Fischer projection is mostly used for linear monosaccharides. The vertical backbone is assumed to form a bridge-like structure on the paper plane with the substituents sticking up:

Newman projection

The Newman projection and the Sawhorse projection are used to depict the stereochemistry at two connected carbon atoms:

Haworth projection

The Haworth projection is used for cyclic sugars:

Skeletal formulas

Skeletal formulas are the standard notation for more complex organic molecules. Carbon (C) atoms are represented by the vertices (corners) and termini of line segments that are not marked with an atomic symbol. Each carbon atom is in turn assumed to bear enough hydrogen atoms to give the carbon atom four bonds. Hydrogen atoms on atoms other than carbon must be written explicitly.

Chirality in skeletal formulas is indicated by the Natta projection method. Solid or dashed wedged bonds represent bonds pointing above-the-plane or below-the-plane of the paper, respectively.

References

External links

• The Importance of Structural Formulas
• Structural formulas