Propanamide

Last updated
Propanamide
Skeletal formula Propanamide-2D-skeletal.png
Skeletal formula
Ball-and-stick model Propionamide-3D-balls.png
Ball-and-stick model
Names
Preferred IUPAC name
Propanamide
Other names
n-propylamide
Propionamide
Propylamide
Propionic amide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.066 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-182-6
MeSH C034666
PubChem CID
UNII
  • InChI=1S/C3H7NO/c1-2-3(4)5/h2H2,1H3,(H2,4,5) X mark.svgN
    Key: QLNJFJADRCOGBJ-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C3H7NO/c1-2-3(4)5/h2H2,1H3,(H2,4,5)
    Key: QLNJFJADRCOGBJ-UHFFFAOYAE
  • CCC(=O)N
Properties
C3H7NO
Molar mass 73.095 g·mol−1
Appearanceliquid , yellow
Density 1.042 g/mL
Melting point 80 °C (176 °F; 353 K)
Boiling point 213 °C (415 °F; 486 K)
very soluble in water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Propanamide has the chemical formula CH3CH2C=O(NH2). [1] It is the amide of propanoic acid.

Contents

This organic compound is a mono-substituted amide. [2] Organic compounds of the amide group can react in many different organic processes to form other useful compounds for synthesis.

Preparation

Propanamide can be prepared by the condensation reaction between urea and propanoic acid:

or by the dehydration of ammonium propionate:

Reactions

Propanamide being an amide can participate in a Hoffman rearrangement to produce ethylamine gas.

Related Research Articles

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.

<span class="mw-page-title-main">Amide</span> Organic compounds of the form RC(=O)NR′R″

In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula R−C(=O)−NR′R″, where R, R', and R″ represent any group, typically organyl groups or hydrogen atoms. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid with the hydroxyl group replaced by an amine group ; or, equivalently, an acyl (alkanoyl) group joined to an amine group.

<span class="mw-page-title-main">Acid–base reaction</span> Chemical reaction between an acid and a base

In chemistry, an acid–base reaction is a chemical reaction that occurs between an acid and a base. It can be used to determine pH via titration. Several theoretical frameworks provide alternative conceptions of the reaction mechanisms and their application in solving related problems; these are called the acid–base theories, for example, Brønsted–Lowry acid–base theory.

<span class="mw-page-title-main">Peptide bond</span> Covalent chemical bond between amino acids in a peptide or protein chain

In organic chemistry, a peptide bond is an amide type of covalent chemical bond linking two consecutive alpha-amino acids from C1 of one alpha-amino acid and N2 of another, along a peptide or protein chain.

In chemistry, an acid dissociation constant is a quantitative measure of the strength of an acid in solution. It is the equilibrium constant for a chemical reaction

<span class="mw-page-title-main">Base (chemistry)</span> Type of chemical substance

In chemistry, there are three definitions in common use of the word "base": Arrhenius bases, Brønsted bases, and Lewis bases. All definitions agree that bases are substances that react with acids, as originally proposed by G.-F. Rouelle in the mid-18th century.

In chemistry, azide is a linear, polyatomic anion with the formula N−3 and structure N=N+=N. It is the conjugate base of hydrazoic acid HN3. Organic azides are organic compounds with the formula RN3, containing the azide functional group. The dominant application of azides is as a propellant in air bags.

In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group. The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH3CH2C≡N is called "propionitrile". The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.

<span class="mw-page-title-main">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

The Brønsted–Lowry theory (also called proton theory of acids and bases) is an acid–base reaction theory which was first developed by Johannes Nicolaus Brønsted and Thomas Martin Lowry independently in 1923. The basic concept of this theory is that when an acid and a base react with each other, the acid forms its conjugate base, and the base forms its conjugate acid by exchange of a proton (the hydrogen cation, or H+). This theory generalises the Arrhenius theory.

Cyclopropene is an organic compound with the formula C3H4. It is the simplest cycloalkene. Because the ring is highly strained, cyclopropene is difficult to prepare and highly reactive. This colorless gas has been the subject for many fundamental studies of bonding and reactivity. It does not occur naturally, but derivatives are known in some fatty acids. Derivatives of cyclopropene are used commercially to control ripening of some fruit.

Hydantoin, or glycolylurea, is a heterocyclic organic compound with the formula CH2C(O)NHC(O)NH. It is a colorless solid that arises from the reaction of glycolic acid and urea. It is an oxidized derivative of imidazolidine. In a more general sense, hydantoins can refer to groups or a class of compounds with the same ring structure as the parent compound. For example, phenytoin (mentioned below) has two phenyl groups substituted onto the number 5 carbon in a hydantoin molecule.

Thiourea is an organosulfur compound with the formula SC(NH2)2 and the structure H2N−C(=S)−NH2. It is structurally similar to urea, except that the oxygen atom is replaced by a sulfur atom ; however, the properties of urea and thiourea differ significantly. Thiourea is a reagent in organic synthesis. Thioureas are a broad class of compounds with the general structure R2N−C(=S)−NR2.

<span class="mw-page-title-main">Hemiaminal</span> Organic compound or group with a hydroxyl and amine attached to the same carbon

In organic chemistry, a hemiaminal is a functional group or type of chemical compound that has a hydroxyl group and an amine attached to the same carbon atom: −C(OH)(NR2)−. R can be hydrogen or an alkyl group. Hemiaminals are intermediates in imine formation from an amine and a carbonyl by alkylimino-de-oxo-bisubstitution. Hemiaminals can be viewed as a blend of aminals and geminal diol. They are a special case of amino alcohols.

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

Triflic acid, the short name for trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest known acids. Triflic acid is mainly used in research as a catalyst for esterification. It is a hygroscopic, colorless, slightly viscous liquid and is soluble in polar solvents.

<span class="mw-page-title-main">Diketene</span> Organic compound with formula (CH2CO)2

Diketene is an organic compound with the molecular formula C4H4O2, and which is sometimes written as (CH2CO)2. It is formed by dimerization of ketene, H2C=C=O. Diketene is a member of the oxetane family. It is used as a reagent in organic chemistry. It is a colorless liquid.

In chemistry, the amino radical, ·NH2, also known as the aminyl radical or azanyl radical, is the neutral form of the amide ion. Aminyl radicals are highly reactive and consequently short-lived, like most radicals; however, they form an important part of nitrogen chemistry. In sufficiently high concentration, amino radicals dimerise to form hydrazine. While NH2 as a functional group is common in nature, forming a part of many compounds, the radical cannot be isolated in its free form.

Nickel compounds are chemical compounds containing the element nickel which is a member of the group 10 of the periodic table. Most compounds in the group have an oxidation state of +2. Nickel is classified as a transition metal with nickel(II) having much chemical behaviour in common with iron(II) and cobalt(II). Many salts of nickel(II) are isomorphous with salts of magnesium due to the ionic radii of the cations being almost the same. Nickel forms many coordination complexes. Nickel tetracarbonyl was the first pure metal carbonyl produced, and is unusual in its volatility. Metalloproteins containing nickel are found in biological systems.

In chemistry, ammonolysis (/am·mo·nol·y·sis/) is the process of splitting ammonia into . Ammonolysis reactions can be conducted with organic compounds to produce amines (molecules containing a nitrogen atom with a lone pair, :N), or with inorganic compounds to produce nitrides. This reaction is analogous to hydrolysis in which water molecules are split. Similar to water, liquid ammonia also undergoes auto-ionization, , where the rate constant is k = 1.9 × 10-38.

References

  1. Ramazani, Ali; Rouhani, Morteza; Joo, Sang Woo (2016-01-01). "Catalyst-free sonosynthesis of highly substituted propanamide derivatives in water". Ultrasonics Sonochemistry. 28: 393–399. doi:10.1016/j.ultsonch.2015.08.019. ISSN   1350-4177. PMID   26384923.
  2. Ye, Xuewei; Chai, Weiyun; Lian, Xiao-Yuan; Zhang, Zhizhen (2017-06-18). "Novel propanamide analogue and antiproliferative diketopiperazines from mangrove Streptomyces sp. Q24" . Natural Product Research. 31 (12): 1390–1396. doi:10.1080/14786419.2016.1253079. ISSN   1478-6419. PMID   27806640. S2CID   24563632.