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Structural formula - Wikipedia

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Structural formula
From Wikipedia, the free encyclopedia

The structural formula of a chemical compound is a
graphic representation of the molecular structure,
showing how the atoms are arranged. The chemical
bonding within the molecule is also shown, either
explicitly or implicitly. Unlike chemical formulas, which
have a limited number of symbols and are capable of
only limited descriptive power, structural formulas
provide a complete geometric representation of the
molecular structure. For example, many chemical
compounds exist in different isomeric forms, which have
different enantiomeric structures but the same chemical
formula. A structural formula is able to indicate
arrangements of atoms in three dimensional space in a
way that a chemical formula may not be able to do.
Several systematic chemical naming formats, as in
chemical databases, are used that are equivalent to, and
as powerful as, geometric structures. These chemical
nomenclature systems include SMILES, InChI and
CML. These systematic chemical names can be
converted to structural formulas and vice versa, but
chemists nearly always describe a chemical reaction or
synthesis using structural formulas rather than chemical
names, because the structural formulas allow the chemist
to visualize the molecules and the structural changes that
occur in them during chemical reactions.

Skeletal structural formula of Vitamin B12. Many
organic molecules are too complicated to be
specified with a chemical formula (molecular
formula).

Contents
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Lewis structures
Condensed formulas
Skeletal formulas
Indication of stereochemistry
4.1 Stereochemistry in skeletal formulas
4.2 Unspecified stereochemistry
Perspective drawings
5.1 Newman projection and sawhorse projection
5.2 Cyclohexane conformations
5.3 Haworth projection
5.4 Fischer projection
See also
References
External links

Lewis structures
02.11.2016 23:05

11. This notation is mostly used for small molecules.. pairs of dots may be used to represent bonding pairs. Lewis structures (or "Lewis dot structures") are flat graphical formulas that show atom connectivity and lone pair or unpaired electrons. the carbon atoms are implied to be located at the vertices (corners) and termini of line segments rather than being indicated with the atomic symbol C. Each line represents the two electrons of a single bond. including hydrogen atoms.wikipedia. Alternatively. In this type of diagram. was an aspiring chemist struggling to understand early chemical publications.Structural formula . the inventor of the condensed formulas.php?title=Structural_formula&printa. The presence of a positive or 02. Hydrogen atoms attached to carbon atoms are not indicated: each carbon atom is understood to be associated with enough hydrogen atoms to give the carbon atom four bonds.2016 23:05 . indicating attachment to the nearest non-hydrogen atom on the left when appearing within a formula. Two or three parallel lines between pairs of atoms represent double or Representation of molecules by molecular formula triple bonds. but not threedimensional structure. first used by the organic chemist Friedrich August Kekulé von Stradonitz. all non-bonded electrons (paired or unpaired) and any formal charges on atoms are indicated. Skeletal formulas Skeletal formulas are the standard notation for more complex organic molecules. respectively. Although this system tends to be problematic in application to cyclic compounds. To assist him and his students in future years he invented this simplified version. all atoms are shown..Wikipedia 2 von 6 https://en. it remains a convenient way to represent simple structures: CH3CH2OH (ethanol) Parentheses are used to indicate multiple identical groups. The Lewis structure of water Condensed formulas Ean Rodrigo. or to the atom on the right when appearing at the start of a formula: (CH3)2CHOH or CH(CH3)2OH (2-propanol) In all cases. In addition.org/w/index.

. Skeletal formula of strychnine. negative charge at a carbon atom takes the place of one of the implied hydrogen atoms. Unspecified stereochemistry Fructose. Skeletal formula of isobutanol. For example. while a dashed wedged bond seen for example at the hydrogen (H) at bottom indicates a below-the-plane bond. A crossed double-bond has been used sometimes. Stereochemistry in skeletal formulas Chirality in skeletal formulas is indicated by the Natta projection method.Wikipedia 3 von 6 https://en. with a bond at the hydroxyl (OH) group upper left of image with unknown or unspecified stereochemistry.wikipedia. respectively.org/w/index. Wavy single bonds are the standard way to represent unknown or unspecified stereochemistry or a mixture of isomers (as with tetrahedeal stereocenters). but is no longer considered an acceptable style for general use. sometimes closing with one stereochemistry and sometimes with the other.php?title=Structural_formula&printa. [1][1] 02. A solid wedged bond seen for example at the nitrogen (N) at top indicates a bond pointing abovethe-plane.2016 23:05 . Skeletal formulae can depict cis and trans isomers of alkenes. Wavy single bonds represent unknown or unspecified stereochemistry or a mixture of isomers. Solid or dashed wedged bonds represent bonds pointing abovethe-plane or below-the-plane of the paper. In this case the two possible ring structures are in chemical equilibrium with each other and also with the open-chain structure.. Hydrogen atoms attached to atoms other than carbon must be written explicitly.group at the left. (CH3)2CHCH2OH Indication of stereochemistry Several methods exist to picture the three-dimensional arrangement of atoms in a molecule (stereochemistry). the diagram to the left shows the fructose molecule with a wavy bond to the HOCH2. The ring continually opens and closes.Structural formula .11.

Axial and equatorial positions are not distinguished.php?title=Structural_formula&printa. Bonds in front may or may not be highlighted with stronger lines or wedges.11. Chair conformation of beta-D-Glucose Haworth projection The Haworth projection is used for cyclic sugars. 02. the front carbon is usually on the left and is always slightly lower: Newman projection of butane sawhorse projection of butane Cyclohexane conformations Certain conformations of cyclohexane and other small-ring compounds can be shown using a standard convention. Perspective drawings Newman projection and sawhorse projection The Newman projection and the sawhorse projection are used to depict specific conformers or to distinguish vicinal stereochemistry..wikipedia.Wikipedia 4 von 6 https://en. the sawhorse projection looking at the same bond but from a somewhat oblique vantage point. substituents are positioned directly above or below the ring atom to which they are connected.. In both cases. distinguishing the substituents on the front carbon from the substituents on the back carbon. The only difference is a slightly different perspective: the Newman projection looking straight down the bond of interest.Structural formula . two specific carbon atoms and their connecting bond are the center of attention. Hydrogen substituents are typically omitted. In the Newman projection. For example. instead. the standard chair conformation of cyclohexane involves a perspective view from slightly above the average plane of the carbon atoms and indicates clearly which groups are axial and which are equatorial. a circle is used to represent a plane perpendicular to the bond.org/w/index.2016 23:05 . In the sawhorse projection.

.xtal.edu/ch106-01/strform.1351/pac200678101897.clackamas. pointing toward the observer.2016 23:05 .11. doi:10. Nonetheless. the Fischer projection is a simple way of depicting multiple sequential stereocenters that does not require or imply any knowledge of actual conformation: Fischer projection of D-Glucose See also Molecular graph Chemical formula Valency interaction formula Side chain References 1.csic.htm) Structural formulas (http://dl. Chem. At any given carbon center.es/Cristalografia/indexen.org. External links The Importance of Structural Formulas (http://www.. as a saccharide would never adopt this multiply eclipsed conformation.lb/en/themes/Sciences/Chemistry /Organicchemistry/StructuralFormulas/StructuralFormulas. J. Brecher (2006). while horizontal lines are equivalent to wedges.php?title=Structural_formula&printa.cartage.htm) How to get structural formulas using crystallography (http://www.wikipedia.html) 02. vertical bond lines are equivalent to stereochemical hashed markings. 78 (10): 1897–1970.Structural formula . Haworth projection of beta-D-Glucose Fischer projection The Fischer projection is mostly used for linear monosaccharides. Pure Appl. The projection is totally unrealistic. directed away from the observer.Wikipedia 5 von 6 https://en.org/w/index.iqfr. "Graphical representation of stereochemical configuration (IUPAC Recommendations 2006)" (PDF).

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