Pentyl group

Last updated
Pentyl group
N-pentyl.png
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C5H11/c1-3-5-4-2/h1,3-5H2,2H3 Yes check.svgY
    Key: BFKVXNPJXXJUGQ-UHFFFAOYSA-N Yes check.svgY
  • [CH2]CCCC
Properties
−C5H11
Molar mass 71.1408 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pentyl is a five-carbon alkyl group or substituent with chemical formula -C5H11. It is the substituent form of the alkane pentane.

Contents

In older literature, the common non-systematic name amyl was often used for the pentyl group. Conversely, the name pentyl was used for several five-carbon branched alkyl groups, distinguished by various prefixes. The nomenclature has now reversed, with "amyl" being more often used to refer to the terminally branched group also called isopentyl, as in amobarbital.

A cyclopentyl group is a ring with the formula -C5H9.

The name is also used for the pentyl radical, a pentyl group as an isolated molecule. This free radical is only observed in extreme conditions. [1] Its formula is often written "C
5H
11•" or "• ⁠C
5H
11" to indicate that it has one unsatisfied valence bond. Radicals like pentyl are reactive, they react with neighboring atoms or molecules (like oxygen, water, etc.)

Older "pentyl" groups

The following names are still used sometimes:

NameStructureIUPAC statusIUPAC recomm.Examples
n-pentyl, amylH
3C−(CH
2)
4−		pentyl [2]
tert-pentylH
3C−CH
2−(H
3C−)
2C−		No longer recommended [3] 2-methylbutan-2-yl (aka (1,1-Dimethylpropyl) [3] [4]
neopentyl(H
3C−)
3C−CH
2−		No longer recommended [3] 2,2-dimethylpropyl [3] [5]
isopentyl, amyl,isoamyl(H
3C−)
2CH−(CH
2)
2−		No longer recommended [3] 3-methylbutyl [3] [6]
sec-pentylH
3C−(CH
2)
2−(H
3C−)CH−		pentan-2-yl [7] (or (1-methylbutyl)) [8]
3-pentyl(H
3C−CH
2−)
2CH−		pentan-3-yl (also known as (1-Ethylpropyl)) [9]
sec-isopentyl(H
3C−)
2CH−(H
3C−)CH−		3-methylbutan-2-yl (or (1,2-Dimethylpropyl)
active pentylH
3C−CH
2−(H
3C−)CH−CH
2−		2-methylbutyl

Pentyl radical

The free radical pentyl was studied by J. Pacansky and A. Gutierrez in 1983. [1] The radical was obtained by exposing bishexanoyl peroxide trapped in frozen argon to ultraviolet light, that caused its decomposition into two carbon dioxide (CO
2) molecules and two pentyl radicals.

Examples

Related Research Articles

<span class="mw-page-title-main">Amyl nitrite</span> Chemical compound

Amyl nitrite is a chemical compound with the formula C5H11ONO. A variety of isomers are known, but they all feature an amyl group attached to the nitrite functional group. The alkyl group is unreactive and the chemical and biological properties are mainly due to the nitrite group. Like other alkyl nitrites, amyl nitrite is bioactive in mammals, being a vasodilator, which is the basis of its use as a prescription medicine. As an inhalant, it also has a psychoactive effect, which has led to its recreational use, with its smell being described as that of old socks or dirty feet. It is also referred to as banapple gas.

<span class="mw-page-title-main">Methyl radical</span> Chemical compound

Methyl radical is an organic compound with the chemical formula CH•
3. It is a metastable colourless gas, which is mainly produced in situ as a precursor to other hydrocarbons in the petroleum cracking industry. It can act as either a strong oxidant or a strong reductant, and is quite corrosive to metals.

In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term alkyl is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of −CnH2n+1. A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula −CnH2n−1. Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula −CH3.

<span class="mw-page-title-main">Iodoform</span> Chemical compound

Iodoform (also known as triiodomethane and, inaccurately, as carbon triiodide) is the organoiodine compound with the chemical formula CHI3. A pale yellow, crystalline, volatile substance, it has a penetrating and distinctive odor (in older chemistry texts, the smell is sometimes referred to as that of hospitals, where the compound is still commonly used) and, analogous to chloroform, sweetish taste. It is occasionally used as a disinfectant.

<span class="mw-page-title-main">Amyl nitrate</span> Chemical compound

Amyl nitrate is the chemical compound with the formula CH3(CH2)4ONO2. This molecule consists of the 5-carbon amyl group attached to a nitrate functional group. It is the ester of amyl alcohol and nitric acid.

In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the Nomenclature of Organic Chemistry. Ideally, every possible organic compound should have a name from which an unambiguous structural formula can be created. There is also an IUPAC nomenclature of inorganic chemistry.

In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula −CH2CH2CH3 for the linear form. This substituent form is obtained by removing one hydrogen atom attached to the terminal carbon of propane. A propyl substituent is often represented in organic chemistry with the symbol Pr.

<span class="mw-page-title-main">Acrylic acid</span> Chemical compound

Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.

In organic chemistry, butyl is a four-carbon alkyl radical or substituent group with general chemical formula −C4H9, derived from either of the two isomers (n-butane and isobutane) of butane.

In organic chemistry, a substituent is one or a group of atoms that replaces atoms, thereby becoming a moiety in the resultant (new) molecule.

<span class="mw-page-title-main">Bicyclic molecule</span> Molecule with two joined rings

In chemistry, a bicyclic molecule is a molecule that features two joined rings. Bicyclic structures occur widely, for example in many biologically important molecules like α-thujene and camphor. A bicyclic compound can be carbocyclic, or heterocyclic, like DABCO. Moreover, the two rings can both be aliphatic, or can be aromatic, or a combination of aliphatic and aromatic.

<span class="mw-page-title-main">Amyl acetate</span> Chemical compound

Amyl acetate (pentyl acetate) is an organic compound and an ester with the chemical formula CH3COO[CH2]4CH3 and the molecular weight 130.19 g/mol. It is colorless and has a scent similar to bananas and apples. The compound is the condensation product of acetic acid and 1-pentanol. However, esters formed from other pentanol isomers (amyl alcohols), or mixtures of pentanols, are often referred to as amyl acetate. The symptoms of exposure to amyl acetate in humans are dermatitis, central nervous system depression, narcosis and irritation to the eyes and nose.

<span class="mw-page-title-main">Neopentane</span> Chemical compound

Neopentane, also called 2,2-dimethylpropane, is a double-branched-chain alkane with five carbon atoms. Neopentane is a flammable gas at room temperature and pressure which can condense into a highly volatile liquid on a cold day, in an ice bath, or when compressed to a higher pressure.

<span class="mw-page-title-main">Isopentane</span> Chemical compound

Isopentane, also called methylbutane or 2-methylbutane, is a branched-chain saturated hydrocarbon with five carbon atoms, with formula C
5H
12 or CH(CH
3)
2(C
2H
5).

2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.

<span class="mw-page-title-main">Isoamyl alcohol</span> Chemical compound

Isoamyl alcohol is a colorless liquid with the formula C
5H
12O, specifically (H3C–)2CH–CH2–CH2–OH. It is one of several isomers of amyl alcohol (pentanol). It is also known as isopentyl alcohol, isopentanol, or (in the IUPAC recommended nomenclature) 3-methyl-butan-1-ol. An obsolete name for it was isobutyl carbinol.

In organic chemistry, the acetoxy group, is a functional group with the formula −OCOCH3 and the structure −O−C(=O)−CH3. As the -oxy suffix implies, it differs from the acetyl group by the presence of an additional oxygen atom. The name acetoxy is the short form of acetyl-oxy.

<span class="mw-page-title-main">Phenyl isothiocyanate</span> Chemical compound

Phenyl isothiocyanate (PITC) is a reagent used in reversed phase HPLC. PITC is less sensitive than o-phthaldehyde (OPA) and cannot be fully automated. PITC can be used for analysing secondary amines, unlike OPA. It is also known as Edman's reagent and is used in Edman degradation.

<span class="mw-page-title-main">Propadiene</span> Organic compound (H2C=C=CH2)

Propadiene or allene is the organic compound with the formula H2C=C=CH2. It is the simplest allene, i.e. a compound with two adjacent carbon double bonds. As a constituent of MAPP gas, it has been used as a fuel for specialized welding.

<span class="mw-page-title-main">Thiosemicarbazide</span> Chemical compound

Thiosemicarbazide is the chemical compound with the formula H2NC(S)NHNH2. A white, odorless solid, it is related to thiourea (H2NC(S)NH2) by the insertion of an NH center. They are commonly used as ligands for transition metals. Many thiosemicarbazides are known. These feature an organic substituent in place of one or more H's of the parent molecule. 4-Methyl-3-thiosemicarbazide is a simple example.

References

  1. 1 2 J. Pacansky , A. Gutierrez (1983), "Infrared spectra of the n-butyl and n-pentyl radicals". Journal of Physical Chemistry volume 87, issue 16, pages 3074–3079 doi:10.1021/j100239a023
  2. ↑ n-pentyl nitrite, described as "a nitrite ester having n-pentyl as the alkyl group." Accessed on 2013-02-21
  3. 1 2 3 4 5 6 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 607. doi:10.1039/9781849733069-FP001. ISBN   978-0-85404-182-4.
  4. ↑ NCBI, tert-pentyl alcohol in PubChem. Accessed on 2013-02-21
  5. ↑ neopentyl at CHEBI. Accessed on 2013-02-21
  6. ↑ isopentyl group at CHEBI. Accessed on 2013-02-21
  7. ↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 362. doi:10.1039/9781849733069-FP001. ISBN   978-0-85404-182-4.
  8. ↑ Pentobarbital at CHEBI, described as "Barbituric acid substituted at C-5 by ethyl and sec-pentyl groups". Accessed on 2013-02-21
  9. ↑ Pentan-3-yl group at CHEBI. Accessed on 2013-02-21
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