How to Name Amines
- Make sure you have an amine, and not an amide (an amide has a C=O attached right beside the N)
- Find the longest carbon chain that has N attached to it. ...
- Create the root of your molecule name: An eight-carbon chain with the N attached at Carbon #3 will be octan-3-amine.
- Add substitutents as required. ...
What is the general formula of imines?
Imines are compounds with a C=N double bond. Their general formula is R2C=NR. Here are some examples with their names: CH3CH2CH2CH2CH2CH=NH
How do you make imines from amines?
Synthesis of imines. Imines are typically prepared by the condensation of primary amines and aldehydes and less commonly ketones: In terms of mechanism, such reactions proceed via the nucleophilic addition giving a hemiaminal -C(OH)(NHR)- intermediate, followed by an elimination of water to yield the imine.
How do you name aldimines?
One way of naming aldimines is to take the name of the radical, remove final "e", and add "-imine", for example ethanimine.
What is the difference between imine and tosylimine?
An imine can be oxidized with meta-chloroperoxybenzoic acid (mCPBA) to give an oxaziridine A tosylimine reacts with an α,β-unsaturated carbonyl compound to an allylic amine in the Aza-Baylis–Hillman reaction . Imines are intermediates in the alkylation of amines with formic acid in the Eschweiler-Clarke reaction .
What is imines formula?
Imines are chemical molecules with a double bond between carbon and nitrogen (C=N). They are made by substituting the oxygen atom in aldehydes and ketones with the (N-R) group. Imines are compounds with a C=N double bond. Their general formula is R2C=NR.
What are imines with examples?
Imines are common ligands in coordination chemistry. Particularly popular examples are found with Schiff base ligands derived from salicylaldehyde, the salen ligands. Metal-catalyzed reactions of imines proceed through such complexes. In classical coordination complexes, imines bind metals through nitrogen.
How do you name an amino group?
The amine group is located by the position number. Groups that are attached to the nitrogen atom are located using “N” as the position number. More complex primary amines are named with —NH2 as the amino substituent. Aromatic amines: named as derivatives of the parent compound aniline.
What do you mean by imine?
imine. [ ĭm′ēn′, -ĭn, ĭ-mēn′ ] A compound derived from ammonia and containing an NH group attached by a double bond to a carbon atom in another group. The radical CNH, having a double bond between the carbon and nitrogen atoms.
What is the role of imines?
Imines and their derivatives have long been recognized as key intermediates for the synthesis of nitrogen heterocycles, especially in the arena of alkaloid synthesis.
What are imines used for?
IminesDrugDrug DescriptionAzelnidipineFor the treatment of hypertension.UlodesineUlodesine has been used in trials studying the treatment of Gout, Arthritis, Hyperuricemia, and Joint Disease.13 more rows
How do you name ch3ch2nh2?
Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor.
What is an anime in chemistry?
Amines are one of the most important classes of organic compounds which can be derived when we replace one or more hydrogen atoms of ammonia molecule with an alkyl group.
What is the COOH group called?
carboxylThe carboxyl (COOH) group is so-named because of the carbonyl group (C=O) and hydroxyl group. The chief chemical characteristic of the carboxylic acids is their acidity.
What is imine and amine?
An imine is a functional group containing a carbon-nitrogen double bond. Nitrogen is linked with either hydrogen or a carbon atom. 2. An amine is a derivative of ammonia formed by substituting one or more hydrogen atoms with alkyl or aryl groups.
What is substituted imine called?
The substituted imine is called a Schiff's base.
Which of the following is an imine?
Et3N.
How are imines formed?
Imines are formed when any primary amine reacts with an aldehyde or ketone under appropriate conditions. Imine formation requires an acid catalyst, otherwise the reaction is very slow. The acid is needed for the elimination of water.
What is amine and imine?
An amine is a functional group in which one or more hydrogen atoms are replaced by an alkyl or aryl group. An imine is a functional group containing a carbon-nitrogen double bond. Nitrogen is linked with either hydrogen or a carbon atom.
What is the structure of hydrazone?
Hydrazones are a class of organic compounds with the structure R 1R 2C=N−NH 2. They are related to ketones and aldehydes by the replacement of the oxygen =O. with the = N−NH 2 functional group. They are formed usually by the action of hydrazine on ketones or aldehydes.
What is Hemiaminal group?
A hemiaminal (also carbinolamine) 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.
How are imines formed?
Imines are typically prepared by the condensation of primary amines and aldehydes and less commonly ketones. In terms of mechanism, such reactions proceed via the nucleophilic addition giving a hemiaminal -C (OH) (NHR)- intermediate, followed by an elimination of water to yield the imine (see alkylimino-de-oxo-bisubstitution for a detailed mechanism). The equilibrium in this reaction usually favors the carbonyl compound and amine, so that azeotropic distillation or use of a dehydrating agent, such as molecular sieves or magnesium sulfate, is required to push the reaction in favor of imine formation. In recent years, several reagents such as Tris (2,2,2-trifluoroethyl)borate [B (OCH 2 CF 3) 3 ], pyrrolidine or titanium ethoxide [Ti (OEt) 4] have been shown to catalyse imine formation.
What is the structure of an imine?
The general structure of an imine. An imine ( / ɪˈmiːn / or / ˈɪmɪn /) is a functional group or chemical compound containing a carbon – nitrogen double bond. The nitrogen atom can be attached to a hydrogen (H) or an organic group (R).
What is the name of the imine that is attached to both hydrocarbyls?
A primary imine in which C is attached to both a hydrocarbyl and a H is called a primary aldimine ; a secondary imine with such groups is called a secondary aldimine. A primary imine in which C is attached to two hydrocarbyls is called a primary ketimine; a secondary imine with such groups is called a secondary ketimine. Primary aldimine .
What are imines used for?
Imines are widely used as intermediates in the synthesis of heterocycles. Aromatic imines reacts with an enol ether to a quinoline in the Povarov reaction. The C=N bond in imines is reactive toward cycloadditions. Imines react, thermally, with ketenes in [2+2] cycloadditions to form β-lactams in the Staudinger synthesis. An imine can be oxidized with meta-chloroperoxybenzoic acid (mCPBA) to give an oxaziridine
How are imines related to ketones?
Imines are related to ketones and aldehydes by replacement of the oxygen with an NR group. When R = H, the compound is a primary imine, when R is hydrocarbyl, the compound is a secondary imine. Imines exhibit diverse reactivity and are commonly encountered throughout chemistry. When R 3 is OH, the imine is called an oxime, ...
What is the formula for aldimines?
An aldimine is an imine that is an analog of an aldehyde. As such, aldimines have the general formula R–CH=N–R'. Aldimines are similar to ketimines, which are analogs of ketones .
What reacts with an amine to an aminal?
An imine reacts with an amine to an aminal, see for example the synthesis of cucurbituril.
How to name amines?
This is the brief summary of naming a primary amine: Step 1. Identify the longest carbon chain bonded to the amine nitrogen. Step 2. Identify the substituents. Step 3. Number the parent chain giving the amine the lowest locant. Step 4. Put everything together having the substituents in alphabetical order.
What is the prefix for amino group?
So, remember the suffix and prefix of the amino group; “ amine ” and “ amino ” respectively. And for the alcohol, it is “ hydroxy ” and “ ol ”. Again, the full list of this can be found here.
What are amines used for?
There are lots of amines that are simply referred to by their common names. Most of these are used as organic bases and constitute a part of biologically active and essential compounds such as amino acids, nitrogen-containing pain killers (alkaloids), as well as synthetic medicines.
Which way is the ring numbered?
When other groups are present on the ring, it is numbered clockwise or counterclockwise depending on which direction gives the next substituent the lower number:
Can amines be named by systematic or common names?
In general, amines can be named either by systematic or common names.
Is a secondary amine a primary amine?
If the secondary or a tertiary amine has more than one type of alkyl group, then it is named as a primary amine. The parent chain is the longest chain bonded to the amine, and the other groups are named as substituents connected to the nitrogen and preceded by an “ N ” (in italics).
Overview
Synthesis of imines
Imines are typically prepared by the condensation of primary amines and aldehydes or ketones. Ketones undergo similar reactions, but less commonly than aldehydes. In terms of mechanism, such reactions proceed via the nucleophilic addition giving a hemiaminal -C(OH)(NHR)- intermediate, followed by an elimination of water to yield the imine (see alkylimino-de-oxo-bisubstitution fo…
Structure
For ketimines and aldimines, respectively, the five core atoms (C2C=NX and C(H)C=NX, X = H or C) are coplanar. Planarity results from the sp -hybridization of the mutually double-bonded carbon and the nitrogen atoms. The C=N distance is 1.29-1.31 Å for nonconjugated imines and 1.35 Å for conjugated imines. By contrast, C-N distances in amines and nitriles are 1.47 and 1.16 Å, respectively. Rotation about the C=N bond is slow. Using NMR spectroscopy, both E- and Z-iso…
Nomenclature and classification
The term "imine" was coined in 1883 by the German chemist Albert Ladenburg.
Usually imines refer to compounds with the general formula R2C=NR, as discussed below. In the older literature, imine refers to the aza-analogue of an epoxide. Thus, ethylenimine is the three-membered ring species aziridine C2H4NH. The relationship of imines to amines having double and single bonds can be correlated with imides and amides, as in succinimide vs acetamide.
Reactions
The chief reaction of imines, often undesirable, is their hydrolysis back to the amine and the carbonyl precursor.
R2C=NR' + H2O ⇌ R2C=O + R'NH2
Imines are widely used as intermediates in the synthesis of heterocycles.
• Aromatic imines react with an enol ether to a quinoline in the Povarov reaction.
Biological role
Imines are common in nature. The pyridoxal phosphate-dependent enzymes (PLP enzymes) catalyze myriad reactions involving aldimines (or Schiff bases).
See also
• Enamine
• Schiff base
• Carboximidate
• Oxime
• Oxazolidine