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Encyclopedia > Imine
The general structure of an imine
The general structure of an imine

An imine is a functional group or chemical compound containing a carbon-nitrogen double bond. Imines, due to their diverse reactivity, are common substrates in a wide variety of transformations. An imine can be synthesised by the nucleophilic addition of an amine to a ketone or aldehyde giving a hemiaminal -C(OH)(NHR)- followed by an elimination of water to yield the imine. (see alkylimino-de-oxo-bisubstitution for a detailed mechanism) However, the equilibrium in this reaction usually lies in favor of the free carbonyl compound and amine, so that azeotrope distillation or use of a dehydrating agent such as molecular sieves is required to push the reaction in favor of imine formation. Image File history File links Size of this preview: 611 × 599 pixelsFull resolution (1100 × 1079 pixel, file size: 17 KB, MIME type: image/png) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links Size of this preview: 611 × 599 pixelsFull resolution (1100 × 1079 pixel, file size: 17 KB, MIME type: image/png) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... In organic chemistry, functional groups are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... Covalent bonding is a form of chemical bonding characterized by the sharing of one or more pairs of electrons between atoms, in order to produce a mutual attraction, which holds the resultant molecule together. ... In organic chemistry, a nucleophilic addition reaction is an addition reaction where in a chemical compound a pi bond is removed by the creation of two new covalent bonds by the addition of a nucleophile. ... The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... Ketone group A ketone(key tone) is either the functional group characterized by a carbonyl group (O=C) linked to two other carbon atoms or a chemical compound that contains this functional group. ... An aldehyde. ... Generic hemiaminal 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. ... An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one or two-step mechanism. ... Alkylimino-de-oxo-bisubstitution in organic chemistry is the organic reaction of carbonyl compounds with amines to imines . ... Carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e. ... A molecular sieve is a material containing tiny pores of a precise and uniform size that is used as an adsorbent for gases and liquids. ...


Addition reactions with primary amines give imines that are stable under an inert atmosphere. In the presence of oxygen or water, such imines will quite readily hydrolyze or oligomerize. However, with an aryl group or certain stabilizing alkyl substituents on nitrogen, the imine formed is stable to oxygen and water and is called a Schiff base. In contrast, imine condensations using ammonia and a carbonyl compound do not lead to stable imines - the imine formed quickly oligomerizes such as in the reaction of formaldehyde and ammonia which gives hexamine instead of the corresponding imine. When a secondary amine is used, elimination of water from the hemiaminal leads to an iminium ion. This iminium ion can further react to form either an aminal, or enamine if there is an sp3-hybridized carbon in the alpha position. Addition of suitably activated carbonyl compounds to this imminium ion also leads to the corresponding Mannich base. Ammonia Amines are organic compounds containing nitrogen as the key atom in the amine functional group. ... In the context of organic molecules, aryl refers to any member of the set of functional groups or substituents that are derived from a simple aromatic ring. ... 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. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... a mixture of 4,4-diaminodiphenyl ether 1 (1. ... The chemical compound formaldehyde (also known as methanal) is a gas with a pungent smell. ... Ammonia is a compound with the formula NH3. ... Hexamethylenetetramine cage Hexamine ((CH2)6N4) is a chemical created by the reaction of 6 moles of formaldehyde and 4 moles of ammonia. ... It has been suggested that this article or section be merged into Secondary amine. ... An iminium salt or ion in organic chemistry has the general structure R1-CH=NH+-R2 and is as such a protonated imine. ... A hemiaminal is a functional group or type of chemical compound that has a hydroxyl group and a amine attached to the same carbon atom: -C(OH)(NR2)-. R can be hydrogen or an alkyl group. ... An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H2O. Form Categories: Functional groups | Stub ... In chemistry, hybridisation is the mixing of atomic orbitals to form new orbitals suitable for bonding. ... A mannich base is the reaction product of an amine and a carbonyl compound that engage in a nucleophilic addition reaction followed by elimination to the imine salt. ...

Contents

Imine synthesis

....... Alkylimino-de-oxo-bisubstitution in organic chemistry is the organic reaction of carbonyl compounds with amines to imines . ... A carbanion is an anion in which carbon has an unshared pair of electrons and bears a negative charge usually with three substituents for a total of eight valence electrons [1]. The carbanion exists in a trigonal pyramidal geometry. ... Nitroso refers to a functional group in organic chemistry which has the general formula R-NO. Nitroso compounds can be prepared by the reduction of nitro compounds or by the oxidation of hydroxylamines. ... Dehydration (hypohydration) is the removal of water (hydro in ancient Greek) from an object. ... Generic hemiaminal 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. ... The chemical structure of ethylene, the simplest alkene. ... Hydrazoic acid is a colorless, volatile, and extremely explosive liquid at room temperature and pressure. ... The Schmidt reaction is an organic reaction involving alkyl migration over the carbon to nitrogen chemical bond in an azide with expulsion of nitrogen [1]. A key reagent introducing this azide group is hydrazoic acid and the reaction product depends on the type of reactant: carboxylic acids form amines through...


Imine reactions

Reductive amination is a type of amination reaction which involves the conversion of a carbonyl group to an amine. ... The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... Hydrolysis is a chemical reaction or process in which a chemical compound reacts with water. ... The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... Carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e. ... The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... A hemiaminal is a functional group or type of chemical compound that has a hydroxyl group and a amine attached to the same carbon atom: -C(OH)(NR2)-. R can be hydrogen or an alkyl group. ... Cucurbiturils are macrocyclic molecules consisting of glycoluril repeat units. ... Dienes are hydrocarbons which contain two double bonds. ... The Aza Diels-Alder reaction converts imines and dienes to tetrahydropyridines. ... An enol ether is an alkene with an alkoxy substituent. ... Quinoline, also known as 1-azanaphthalene, 1-benzazine, or benzo[b]pyridine, is a heterocyclic aromatic organic compound. ... Scheme 1. ... The tosylate group with a generic R group attached A tosyl group (abbreviated Ts or Tos) combines the toluene and sulfonyl functional groups. ... In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom. ... An allyl group is an alkene hydrocarbon group with the formula H2C=CH-CH2-. It is made up of a vinyl group, CH2=CH-, attached to a methylene -CH2. ... The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... The Aza-Baylis-Hillman reaction or aza-BH reaction in organic chemistry is a variation of the Baylis-Hillman reaction and describes the reaction of an electron deficient alkene usually an α,β-unsaturated carbonyl compound with an imine in the presence of a nucleophile. ... The Eschweiler-Clarke reaction (also called the Eschweiler-Clarke methylation) is a chemical reaction whereby a primary (or secondary) amine is methylated using excess formic acid and formaldehyde. ... The Amadori rearrangement is an organic reaction describing the acid or base catalyzed isomerization or rearrangement reaction of the N-glycoside of an aldose or the glycosylamine to the corresponding 1-amino-1-deoxy-ketose. ...

See also

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 of primarily carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well... An oxime is one in a class of chemical compounds with the general formula R1R2CNOH, where R1 is an organic side chain and R2 is either hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. ... Benzophenone hydrazone, an example hydrazone In chemistry, a hydrazone is a compound with the structure R2C=NNR2, differing from a ketone or aldehyde by the replacement of the double bonded oxygen with the =NNR2 functional group. ... A nitrile is any organic compound which has a -C≡N functional group. ... An isocyanide (erroneously called isonitrile) is a functional group in organic synthesis containing carbon and nitrogen. ...

References

  • March Jerry; (1985). Advanced Organic Chemistry reactions, mechanisms and structure (3rd ed.). New York: John Wiley & Sons, inc. ISBN 0-471-85472-7

  Results from FactBites:
 
Encyclopedia: Imine (1404 words)
The subsequent reduction of imine to amine is typically accomplished by treating with hydrogen and a suitable hydrogenation catalyst or treating with aluminum-mercury amalgam or via sodium cyanoborohydride.
Isolation of imine and its subsequent reduction are sometimes reported to be more effective than reductive amination, but typically the difficulties in obtaining imines in high yield and their instability argue against that procedure.
Imines derived from ammonia tend to be unstable--they often rapidly hydrolyze even with water to generate carbonyl compound and are often prone to polymerization.
Imine - Wikipedia, the free encyclopedia (295 words)
An imine is a functional group or chemical compound containing a carbon-nitrogen double bond.
An imine can be synthesised by nucleophilic addition from a ketone or aldehyde and ammonia or an amine to a hemiaminal -C(OH)(NHR)- followed by elimination of water to the imine.
an imine reacts with dienes in the Aza Diels-Alder reaction to a tetrahydropyridine.
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