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The skeletal formula of the antidepressant drug escitalopram, featuring skeletal representations of heteroatoms, a triple bond, benzene rings and stereochemistry

The skeletal formula of an organic compound is a shorthand representation of its molecular structure. Skeletal formulae are ubiquitous in organic chemistry because they show complicated structures clearly and they are quick and simple to draw. Image File history File links Question_book-3. ... For other uses, see Skeleton (disambiguation). ... Image File history File links Download high resolution version (1635x1292, 32 KB) File links The following pages link to this file: Escitalopram User:Benjah-bmm27/Gallery ... Image File history File links Download high resolution version (1635x1292, 32 KB) File links The following pages link to this file: Escitalopram User:Benjah-bmm27/Gallery ... Prozac, a selective serotonin reuptake inhibitor (SSRI) Serotonin-norepinephrine reuptake inhibitor, Venlafaxine An antidepressant is a psychiatric medication or other substance (nutrient or herb) used for alleviating depression or dysthymia (milder depression). ... Lexapro pills Escitalopram (Lexapro, Lexaprin, Cipralex, Sipralexa, Entact and Seroplex)[1] is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. ... In the nomenclature of organic chemistry, a heteroatom (from Ancient Greek heteros, different, + atomos) is any atom that is not carbon or hydrogen, typically, but not exclusively, nitrogen, oxygen, sulfur, phosphorus or boron. ... Covalent redirects here. ... Benzene, or Benzol (see also Benzine), is an organic chemical compound and a known carcinogen with the formula C6H6. ... The different types of isomers. ... Benzene is the simplest of the arenes, a family of organic compounds An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. ... Geometry of the water molecule Molecular geometry or molecular structure is the three-dimensional arrangement of the atoms that constitute a molecule, inferred from the spectroscopic studies of the compound. ... Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting primarily of carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, the halogens as...

Carbon skeleton

The term skeletal refers to the carbon skeleton of an organic compound - that is, the chains, branches and/or rings of carbon atoms that form the basis of the structure of an organic molecule. The skeleton may have other atoms or groups of atoms bonded to its carbons. Hydrogen is the most common non-carbon atom bonded to carbon and is not explicitly drawn. Other atoms are known as heteroatoms and groups of atoms are called functional groups, as they give the molecule a function. Heteroatoms and functional groups are known collectively as substituents, as they are considered to be a substitute for the hydrogen atom that would be present in the parent hydrocarbon of the organic compound in question. In the nomenclature of organic chemistry, a heteroatom (from Ancient Greek heteros, different, + atomos) is any atom that is not carbon or hydrogen, typically, but not exclusively, nitrogen, oxygen, sulfur, phosphorus or boron. ... In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... In organic chemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon. ... Look up Hydrocarbon in Wiktionary, the free dictionary. ...

Implicit carbon and hydrogen atoms

The skeletal formula of hexane

In standard chemical formulae, carbon atoms are represented by the symbol C and hydrogen atoms by the symbol H. In skeletal formulae, the location of carbon atoms, and hydrogen atoms bonded to carbon, are not denoted by the symbols C and H, but are implicit. Carbon atoms are implied to exist at each vertex. Carbon atoms are assumed to have four covalent bonds to them, so the number of hydrogen atoms attached to a particular carbon atom can be deduced by subtracting from four the number of bonds drawn to that carbon. the 3rd ingredient in big mac ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... For other uses, see Atom (disambiguation). ... This article is about the chemistry of hydrogen. ... This article just presents the basic definitions. ... Covalent redirects here. ...

For example, in the image to the right, the skeletal formula of hexane is shown. The carbon atom labelled C₁ has only one bond shown to it, so there must also be three hydrogens bonded to it, in order to make its total number of bonds four. The carbon atom labelled C₃ has two bonds to it and is therefore also bonded to two hydrogen atoms. the 3rd ingredient in big mac ...

The skeletal formula of ethanol

Any hydrogen atoms bonded to non-carbon atoms are drawn explicitly. In ethanol, C₂H₅OH, for instance, the hydrogen atom bonded to oxygen is denoted by the symbol H, whereas the hydrogens bonded to carbon atoms are not shown directly. Lines representing heteroatom-hydrogen bonds are usually omitted for clarity and compactness, so a functional group like the hydroxyl group is most often written −OH instead of −O−H. These bonds are sometimes drawn out in full in order to accentuate their presence in reaction mechanisms. Image File history File links Download high resolution version (871x379, 6 KB) Summary Description: Structural formula of en:Ethanol (C2H5OH). ... Image File history File links Download high resolution version (871x379, 6 KB) Summary Description: Structural formula of en:Ethanol (C2H5OH). ... Grain alcohol redirects here. ... Grain alcohol redirects here. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs. ...

Explicit heteroatoms

All atoms that are not carbon or hydrogen are signified by their chemical symbol, i.e. Cl for chlorine, O for oxygen and Na for sodium. These atoms are commonly known as heteroatoms in the context of organic chemistry. A chemical symbol is an abbreviation or short representation of the name of a chemical element. ... General Name, symbol, number chlorine, Cl, 17 Chemical series nonmetals Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... This article is about the chemical element and its most stable form, or dioxygen. ... For sodium in the diet, see Salt. ...

Pseudoelement symbols

There are also symbols that appear to be chemical element symbols, but represent certain very common substituents or indicate an unspecified member of a group of elements. These are known as pseudoelement symbols. The most widely used symbol is Ph, which represents the phenyl group. A list of pseudoelement symbols is shown below: A chemical symbol is an abbreviation or short representation of the name of a chemical element. ... The structure of the phenyl group In chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the functional group with the formula -C6H5 where the six carbon atoms are arranged in a cyclic ring structure. ...

Elements

• X for any halogen atom
• M for any metal atom

This article is about the chemical series. ... This article is about metallic materials. ...

Alkyl groups

• R for any alkyl group or even any substituent at all
• Me for the methyl group
• Et for the ethyl group
• n-Pr for the propyl group
• i-Pr for the isopropyl group
• Bu for the butyl group
• i-Bu for the isobutyl group
• s-Bu for the secondary butyl group
• t-Bu for the tertiary butyl group
• Pn for the pentyl group
• Hx for the hexyl group
• Hp for the heptyl group
• Cy for the cyclohexyl group

An alkyl is a univalent radical containing only carbon and hydrogen atoms arranged in a chain. ... In organic chemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon. ... Methyl group In chemistry, a methyl group is a hydrophobic alkyl functional group derived from methane (CH4). ... In chemistry, an ethyl group is an alkyl functional group derived from ethane (C2H6). ... In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula -C3H7. ... Isopropyl is a term in organic chemistry to refer to a three carbon structure. ... In organic chemistry, butyl is a four-carbon alkyl substituent with chemical formula -C4H9 . ... In organic chemistry, pentyl is a five-carbon alkyl substituent with chemical formula -C5H11. ... the 3rd ingredient in big mac ... Cyclohexane is a cycloalkane with the molecular formula C6H12. ...

Aromatic substituents

• Ar for any aromatic substituent
• Bn for the benzyl group
• Bz for the benzoyl group
• Ph for the phenyl group
• Tol for the tolyl group
• Xy for the xylyl group

Aromaticity is a chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. ... Benzyl is the Organic chemistry term for the radical C6H5CH2-. It is obtained by removing a proton from benzene. ... Structure of benzoyl chloride. ... The structure of the phenyl group In chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the functional group with the formula -C6H5 where the six carbon atoms are arranged in a cyclic ring structure. ... Toluene, also known as methylbenzene or phenylmethane is a clear, water-insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene. ... The term xylenes refers to a group of 3 benzene derivatives which encompasses ortho-, meta-, and para- isomers of dimethyl benzene. ...

Functional groups

• Ac for the acetyl group (Ac is also the symbol for the element actinium. However, actinium is rarely encountered in organic chemistry, so the use of Ac to represent the acetyl group never causes confusion)

Acetyl is the radical of acetic acid. ... General Name, Symbol, Number actinium, Ac, 89 Chemical series actinides Group, Period, Block 3, 7, f Appearance silvery Standard atomic weight (227) g·mol−1 Electron configuration [Rn] 6d1 7s2 Electrons per shell 2, 8, 18, 32, 18, 9, 2 Physical properties Phase solid Density (near r. ...

Leaving groups

See the article leaving group for further information A leaving group is an atom or group of atoms that detaches from a chemical substance. ...

• Bs for the brosyl group
• Ns for the nosyl group
• Tf for the trifyl group
• Ts for tosyl group

The tosylate group with a generic R group attached A tosyl group (abbreviated Ts or Tos) combines the toluene and sulfonyl functional groups. ... The tosylate group with a generic R group attached A tosyl group (abbreviated Ts or Tos) combines the toluene and sulfonyl functional groups. ... Triflate, more formally known as trifluoromethanesulfonate, is a functional group with the formula CF3SO3-. The triflate group is often represented by -OTf, as opposed to -Tf. ... The tosylate group with a generic R group attached A tosyl group (abbreviated Ts or Tos) combines the toluene and sulfonyl functional groups. ...

Multiple bonds

Two atoms can be bonded by sharing more than one pair of electrons. The common bonds to carbon are single, double and triple bonds. Single bonds are most common and are represented by a single, solid line between two atoms in a skeletal formula. Double bonds are denoted by two parallel lines, and triple bonds are shown by three parallel lines.

In more advanced theories of bonding, non-integer values of bond order exist. In these cases, a combination of solid and dashed lines indicate the integer and non-integer parts of the bond order, respectively. The integers are commonly denoted by the above symbol. ... Bond order is the number of bonds between a pair of atoms. ...

Hex-3-ene has an internal carbon-carbon double bond

Hex-1-ene has a terminal double bond

Hex-3-yne has an internal carbon-carbon triple bond

Hex-1-yne has a terminal carbon-carbon triple bond

N.B. in the gallery above, double bonds have been shown in red and triple bonds in blue. This was added for clarity - multiple bonds are not normally coloured in skeletal formulae. A carbon to carbon double bond is a bond between two carbon atoms. ... 1-hexene is a higher olefin, or alkene, with a formula C6H12. ... The structural formula of 2-butyne, a simple alkyne-containing molecule Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms, with the formula CnH2n-2. ... Nota bene is a Latin phrase meaning Note Well, coming from notâre—to note. ...

Benzene rings

Benzene rings are very common in organic compounds. To represent the delocalization of electrons over the six carbon atoms in the ring, a circle is drawn inside the hexagon of single bonds. This style is very common in introductory organic chemistry texts used in schools. Benzene, or Benzol (see also Benzine), is an organic chemical compound and a known carcinogen with the formula C6H6. ... In chemistry, delocalized electrons are electrons in a molecule that do not belong to a single atom or a covalent bond. ... For other uses, see Electron (disambiguation). ...

An alternative style that is more common in academia is the Kekulé structure. Although it could be considered inaccurate as it implies three single bonds and three double bonds (benzene would therefore be 1,3,5-cyclohexatriene), all qualified chemists are fully aware of the delocalization in benzene. Kekulé structures are useful for drawing reaction mechanisms clearly. Kekulé von Stradonitz Friedrich August Kekulé von Stradonitz (September 7, 1829 – July 13, 1896) was a German organic chemist. ... A chemist pours from a round-bottom flask. ... In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs. ...

Stereochemistry

Stereochemistry is conveniently denoted in skeletal formulae: The different types of isomers. ...

• solid lines represent bonds in the plane of the paper or screen
• wedges represent bonds that point out of the plane of the paper or screen, towards the observer
• dashed lines represent bonds that point into the plane of the paper or screen, away from the observer
• wavy lines represent either unknown stereochemistry or a racemic mixture of the two possible enantiomers

2-chloro-2-fluoropentane

The stereochemical skeletal formula of 2-chloro-2-fluoropentane

The other possibility for 2-chloro-2-fluoropentane

The skeletal formula of amphetamine, showing its racemic nature

Covalent redirects here. ... In chemistry, a racemate is a mixture of equal amounts of left- and right-handed stereoisomers of a chiral molecule. ... In chemistry, enantiomers (from the Greek ἐνάντιος, opposite, and μέρος, part or portion) are stereoisomers that are nonsuperimposable complete mirror images of each other, much as ones left and right hands are the same but opposite. ... Image File history File links Download high-resolution version (1100x526, 24 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Amphetamine ... Amphetamine or Amfetamine(Alpha-Methyl-PHenEThylAMINE), also known as beta-phenyl-isopropylamine and benzedrine, is a prescription stimulant commonly used to treat Attention-deficit hyperactivity disorder (ADHD) in adults and children. ...

Hydrogen bonds

Hydrogen bonds are sometimes denoted by dotted or dashed lines An example of a quadruple hydrogen bond between a self-assembled dimer complex reported by Meijer and coworkers. ...

External links

• Drawing organic molecules from chemguide.co.uk