Structural formula

molecules and the structural changes that occur in them

during chemical reactions.

1 Lewis structures
H

Lewis Structure
nucleus

H
bonding electrons

Molecular phenomena
envelope of high
electron density

Representation of molecules by molecular formula

Main article: Lewis structure

Lewis structures (or Lewis dot structures) are at
graphical formulas that show atom connectivity and lone
pair or unpaired electrons, but not three-dimensional
Skeletal structural formula of Vitamin B12. Many organic structure.
This notation is mostly used for small
molecules are too complicated to be specied with a chemical molecules. Each line represents the two electrons of a
formula (molecular formula).
single bond. Two or three parallel lines between pairs of
atoms represent double or triple bonds, respectively. AlThe structural formula of a chemical compound is a ternatively, pairs of dots may be used to represent bondgraphic representation of the molecular structure, show- ing pairs. In addition, all non-bonded electrons (paired or
ing how the atoms are arranged. The chemical bonding unpaired) and any formal charges on atoms are indicated.
within the molecule is also shown, either explicitly or implicitly. Unlike chemical formulas, which have a limited
The Lewis structure of water
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 dierent 2 Condensed formulas
isomeric forms, which have dierent enantiomeric structures but the same chemical formula. A structural for- In early organic-chemistry publications, where use of
mula is able to indicate arrangements of atoms in three graphics was strongly limited, a typographic system arose
dimensional space in a way that a chemical formula may to describe organic structures in a line of text. Although
not be able to do.
this system tends to be problematic in application to cyclic
Several systematic chemical naming formats, as in compounds, it remains a convenient way to represent simchemical databases, are used that are equivalent to, and ple structures:
as powerful as, geometric structures. These chemical CH3 CH2 OH (ethanol)
nomenclature systems include SMILES, InChI and CML.
These systematic chemical names can be converted to Parentheses are used to indicate multiple identical groups,
structural formulas and vice versa, but chemists nearly indicating attachment to the nearest non-hydrogen atom
always describe a chemical reaction or synthesis using on the left when appearing within a formula, or to the
structural formulas rather than chemical names, because atom on the right when appearing at the start of a formula:
the structural formulas allow the chemist to visualize the (CH3 )2 CHOH or CH(CH3 )2 OH (2-propanol)
1

5 PERSPECTIVE DRAWINGS

In all cases, all atoms are shown, including hydrogen sent bonds pointing above-the-plane or below-the-plane
atoms.
of the paper, respectively.

4.2 Unspecied stereochemistry

Skeletal formulas

Main article: Skeletal formula

Skeletal formulas are the standard notation for more complex organic molecules. In this type of diagram, rst
used by the organic chemist Friedrich August Kekul von
Stradonitz, 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. 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. The
presence of a positive or negative charge at a carbon atom
takes the place of one of the implied hydrogen atoms. Hydrogen atoms attached to atoms other than carbon must
be written explicitly.
Skeletal formula of isobutanol, (CH3 )2 CHCH2 OH

Indication of stereochemistry

Fructose, with a bond at the hydroxyl (OH) group upper left of

image with unknown or unspecied stereochemistry.

Wavy single bonds represent unknown or unspecied

stereochemistry or a mixture of isomers. For example,
the diagram to the left shows the fructose molecule with
a wavy bond to the HOCH2 - group at the left. In this case
the two possible ring structures are in chemical equilibrium with each other and also with the open-chain structure. The ring continually opens and closes, sometimes
closing with one stereochemistry and sometimes with the
other.

Skeletal formulae can depict cis and trans isomers of

Several methods exist to picture the three-dimensional ar- alkenes. Wavy single bonds are the standard way to reprerangement of atoms in a molecule (stereochemistry).
sent unknown or unspecied stereochemistry or a mixture
of isomers (as with tetrahedeal stereocenters). A crossed
double-bond has been used sometimes, but is no longer
4.1 Stereochemistry in skeletal formulas
considered an acceptable style for general use. [1][1]

N
H
N
O

5 Perspective drawings

H
H

5.1 Newman projection and sawhorse projection

The Newman projection and the sawhorse projection are

used to depict specic conformers or to distinguish vicinal
Skeletal formula of strychnine. A solid wedged bond seen for ex- stereochemistry. In both cases, two specic carbon atoms
ample at the nitrogen (N) at top indicates a bond pointing above- and their connecting bond are the center of attention.
the-plane, while a dashed wedged bond seen for example at the The only dierence is a slightly dierent perspective: the
hydrogen (H) at bottom indicates a below-the-plane bond.
Newman projection looking straight down the bond of interest, the sawhorse projection looking at the same bond
Chirality in skeletal formulas is indicated by the Natta but from a somewhat oblique vantage point. In the Newprojection method. Solid or dashed wedged bonds repre- man projection, a circle is used to represent a plane per-

3
pendicular to the bond, distinguishing the substituents on
the front carbon from the substituents on the back carbon.
In the sawhorse projection, the front carbon is usually on
the left and is always slightly lower:

6 See also
Molecular graph
Chemical formula

Newman projection of butane

Valency interaction formula

sawhorse projection of butane

Side chain

5.2

Cyclohexane conformations

Certain conformations of cyclohexane and other smallring compounds can be shown using a standard convention. For example, 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. Bonds in front may or may not be highlighted
with stronger lines or wedges.
Chair conformation of beta-D-Glucose

5.3

Haworth projection

The Haworth projection is used for cyclic sugars. Axial and equatorial positions are not distinguished; instead,
substituents are positioned directly above or below the
ring atom to which they are connected. Hydrogen substituents are typically omitted.
Haworth projection of beta-D-Glucose

5.4

Fischer projection

The Fischer projection is mostly used for linear

monosaccharides. At any given carbon center, vertical
bond lines are equivalent to stereochemical hashed markings, directed away from the observer, while horizontal
lines are equivalent to wedges, pointing toward the observer. The projection is totally unrealistic, as a saccharide would never adopt this multiply eclipsed conformation. Nonetheless, the Fischer projection is a simple way
of depicting multiple sequential stereocenters that does
not require or imply any knowledge of actual conformation:
H
O

H
HO

OH
H

OH

OH
CH2OH Fischer projection of D-Glucose

7 References
[1] J. Brecher (2006).
Graphical representation of
stereochemical conguration (IUPAC Recommendations
2006)" (PDF). Pure Appl. Chem. 78 (10): 18971970.
doi:10.1351/pac200678101897.

8 External links
The Importance of Structural Formulas
Structural formulas
How to get structural formulas using crystallography

9 TEXT AND IMAGE SOURCES, CONTRIBUTORS, AND LICENSES

Text and image sources, contributors, and licenses

9.1

Text

Structural formula Source: https://en.wikipedia.org/wiki/Structural_formula?oldid=731230330 Contributors: Tarquin, Jaknouse,

Michael Hardy, Stone, Donarreiskoer, Gentgeen, Bensaccount, OldakQuill, Beland, Discospinster, Cacycle, Vsmith, Mulder1982,
Bobo192, Jag123, Benjah-bmm27, Walkerma, KingTT, TenOfAllTrades, Angr, Mpatel, Palica, Drpaule, YurikBot, Wavelength, Postglock, GeeJo, Nemu, SmackBot, Hansonrstolaf, Liaocyed, Eskimbot, Edgar181, BirdValiant, Ben.c.roberts, MalafayaBot, Sbharris, Deenoe, DJHasis, Philipwhiuk, DMacks, FrozenMan, Mets501, PSUMark2006, JForget, Kupirijo, Tawkerbot4, Christian75, Omicronpersei8, Thijs!bot, Danielle dk, WVhybrid, AntiVandalBot, Roman clef, Couchpotato99, Balloonguy, Dirac66, 28421u2232nfenfcenc,
Allstarecho, Patstuart, Rettetast, CommonsDelinker, J.delanoy, Hans Dunkelberg, Mikael Hggstrm, Kloisiie, VolkovBot, PaulTanenbaum, Eubulides, SieBot, ClueBot, Cmj91uk, Tim32, Kurdo777, Addbot, Xp54321, Wickey-nl, Luckas-bot, Yobot, Daniele Pugliesi,
LilHelpa, Brane.Blokar, Elvim, Br77rino, , FrescoBot, Gwideman, PigFlu Oink, I dream of horses, Armando-Martin, JSquish,
Odysseus1479, Jbergste, BioPupil, ClueBot NG, Jkwchui, Widr, MerlIwBot, Juro2351, Dexbot, ThunderSkunk, Frosty, Library computer,
JPaestpreornJeolhlna, YarLucebith, Hazzalomasrico, Vasanthrojin, Charlesy, Trefecta and Anonymous: 85

9.2

Images

File:Cobalamin.png Source: https://upload.wikimedia.org/wikipedia/commons/e/ec/Cobalamin.png License: Public domain Contributors: Transferred from en.wikipedia
Original artist: Ymwang42 (talk). Original uploader was Ymwang42 at en.wikipedia
File:D-Fructose_cyclic.png Source: https://upload.wikimedia.org/wikipedia/commons/6/61/D-Fructose_cyclic.png License: CC BY 3.0
Contributors: Own work Original artist: Physchim62
File:DGlucose_Fischer.svg Source: https://upload.wikimedia.org/wikipedia/commons/1/14/DGlucose_Fischer.svg License: CC BY-SA
3.0 Contributors: Own work Original artist: Christopher King
File:Skeletal-formulae-alkene-stereochemistry.png
Source:
https://upload.wikimedia.org/wikipedia/commons/5/5a/
Skeletal-formulae-alkene-stereochemistry.png License: Public domain Contributors: Own work Original artist: Ben Mills
File:Structuresandmolecules.svg Source: https://upload.wikimedia.org/wikipedia/commons/1/1f/Structuresandmolecules.svg License:
CC BY-SA 3.0 Contributors: Own work Original artist: Jkwchui
File:Strychnine2.svg Source: https://upload.wikimedia.org/wikipedia/commons/4/41/Strychnine2.svg License: Public domain Contributors: Selfmade with ChemDraw. Original artist: Calvero.

9.3

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