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Hydroxamic acid

 

 
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Hydroxamic acid
 
 
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A hydroxamic acid is a class of chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
s sharing the same functional group
Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
 in which an hydroxylamine
Hydroxylamine

Hydroxylamine is a reactive chemical with chemical formula NH2OH. It can be considered a hybrid of ammonia and water due to parallels it shares with each....
 is inserted into an carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
. Its general structure is R-CO-NH-OH, with an R as an organic residue, a CO as a carbonyl
Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double bond to an oxygen atom : C=O.The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex ; in this situation, carbon is triple-bonded to oxygen : C=O....
 group, and a hydroxylamine
Hydroxylamine

Hydroxylamine is a reactive chemical with chemical formula NH2OH. It can be considered a hybrid of ammonia and water due to parallels it shares with each....
 as NH2-OH. They are used as metal chelator
Chelation

Chelation is the binding or complex of a bi- or multidentate ligand. These ligands, which are often organic compounds, are called chelants, chelators, chelating agents, or sequestration....
s.

Hydroxamic acids can be synthesized from aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
s via the Angeli-Rimini reaction
Angeli-Rimini reaction

The Angeli-Rimini reaction is an organic reaction between an aldehyde and the sulfonamide N-hydroxybenzenesulfonamide in presence of base forming an hydroxamic acid....
. A well-known hydroxamic acid reaction is the Lossen rearrangement
Lossen rearrangement

The Lossen rearrangement is the chemical reaction of a hydroxamic acid 1 with a dehydration agent to form the O-derivative 2, which spontaneously rearranges to form an isocyanate 3....
.

Hydroxamates are essential growth factors, or vitamins, for some microbes.






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Encyclopedia


A hydroxamic acid is a class of chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
s sharing the same functional group
Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
 in which an hydroxylamine
Hydroxylamine

Hydroxylamine is a reactive chemical with chemical formula NH2OH. It can be considered a hybrid of ammonia and water due to parallels it shares with each....
 is inserted into an carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
. Its general structure is R-CO-NH-OH, with an R as an organic residue, a CO as a carbonyl
Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double bond to an oxygen atom : C=O.The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex ; in this situation, carbon is triple-bonded to oxygen : C=O....
 group, and a hydroxylamine
Hydroxylamine

Hydroxylamine is a reactive chemical with chemical formula NH2OH. It can be considered a hybrid of ammonia and water due to parallels it shares with each....
 as NH2-OH. They are used as metal chelator
Chelation

Chelation is the binding or complex of a bi- or multidentate ligand. These ligands, which are often organic compounds, are called chelants, chelators, chelating agents, or sequestration....
s.

Hydroxamic acids can be synthesized from aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
s via the Angeli-Rimini reaction
Angeli-Rimini reaction

The Angeli-Rimini reaction is an organic reaction between an aldehyde and the sulfonamide N-hydroxybenzenesulfonamide in presence of base forming an hydroxamic acid....
. A well-known hydroxamic acid reaction is the Lossen rearrangement
Lossen rearrangement

The Lossen rearrangement is the chemical reaction of a hydroxamic acid 1 with a dehydration agent to form the O-derivative 2, which spontaneously rearranges to form an isocyanate 3....
.

Hydroxamates are essential growth factors, or vitamins, for some microbes. They function as iron-binding compounds (siderophore
Siderophore

A Siderophore is an iron Chelation compound secreted by microorganisms such as bacteria, fungi and grasses. . The bioavailability of iron iron ions is limited by the very low solubility of iron bearing mineral phases such as iron oxides at neutral pH and therefore cannot be utilized by organisms ....
s) that solubilise iron and transport it into the cell.

Iron is a key component of cytochrome
Cytochrome

Cytochromes are, in general, membrane-bound hemoproteins that contain heme groups and carry out electron transport.They are found either as subunitss or as subunits of bigger enzymatic complexes that catalyze redox reactions....
s and iron-sulphur proteins (involved in electron transport) and is thus important in cellular respiration
Cellular respiration

Cellular respiration is the set of the metabolism reactions and processes that take place in organisms' cell s to convert Energy from nutrients into adenosine triphosphate , and then release waste products....
. In an environment, absent from oxygen (anoxic); iron will be present in the ferrous
Ferrous

Ferrous, in chemical science, indicates a bivalent iron compound , as opposed to ferric, which indicates a trivalent iron compound .Outside of chemical science, ferrous is an adjective used to indicate the presence of iron....
 +2 oxidation state (Fe2+), which is water-soluble. Under oxic conditions; iron will be in the ferric
Ferric

Ferric is a term that means containing or having to do with iron, derived from the Latin word ferrum, meaning "iron". In chemistry the term is reserved for iron with an oxidation number of +3, denoted iron or Fe3+, whereas ferrous indicates that it has oxidation number of +2 and is denoted iron or Fe2+....
 +3 oxidation state (Fe3+), in insoluble mineral form. The powerful chelating properties of hydroxamic acid and its derivatives is exploited by bacteria to obtain ferric iron. Once the iron-hydroxamate complex has entered the cell, the iron is liberated and the hydroxamic acid can be excreted and reused for iron transport.