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Hemiaminal
In organic chemistry, 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: . 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. Classification according to amine precursor Addition of ammonia The adducts formed by the addition of ammonia to aldehydes have long been studied. Compounds containing both a primary amino group and a hydroxyl group bonded to the same carbon atom are rare. They are invoked but rarely observed as intermediates in the reaction of ammonia and aldehydes and ketones. One example of this rare functionality is the adduct of ammonia and hexafluoroacetone, . The C-substituted derivatives are obtained by reaction of aldehydes and ammonia: :3 RCHO + 3 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Glycosylamine
Glycosylamines are a class of biochemical compounds consisting of a glycosyl group attached to an amino group, -NR2. They are also known as N-glycosides,. as they are a type of glycoside. Glycosyl groups can be derived from carbohydrates. The glycosyl group and amino group are connected with a β-N-glycosidic bond, forming a cyclic hemiaminal ether bond (α-aminoether). Examples include nucleosides such as adenosine Adenosine (symbol A) is an organic compound that occurs widely in nature in the form of diverse derivatives. The molecule consists of an adenine attached to a ribose via a β-N9- glycosidic bond. Adenosine is one of the four nucleoside building .... References Biomolecules Carbohydrates {{Biochem-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Imine
In organic chemistry, an imine ( or ) is a functional group or organic compound containing a carbon–nitrogen double bond (). The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions. 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 sp2-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-isomers of aldimines have been detected. Owing to steric effects, the E isomer is favored. Nomenclature and classification The term "imine" was coine ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alkylimino-de-oxo-bisubstitution
In organic chemistry, alkylimino-de-oxo-bisubstitution is the organic reaction of carbonyl compounds with amines to imines. The reaction name is based on the IUPAC Nomenclature for Transformations. The reaction is acid catalyzed and the reaction type is nucleophilic addition of the amine to the carbonyl compound followed by transfer of a proton from nitrogen to oxygen to a stable hemiaminal or carbinolamine. With primary amines water is lost in an elimination reaction to an imine. With aryl amines especially stable Schiff bases are formed. Reaction mechanism The reaction steps are reversible reactions and the reaction is driven to completion by removal of water e.g. by azeotropic distillation, molecular sieves or titanium tetrachloride. Primary amines react through an unstable hemiaminal intermediate which then splits off water. : Secondary amines do not lose water easily because they do not have a proton available and instead they often react further to an aminal: : or whe ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hexafluoroacetone
Hexafluoroacetone (HFA) is a chemical compound with the formula (CF3)2CO. It is structurally similar to acetone; however, its reactivity is markedly different. It a colourless, hygroscopic, nonflammable, highly reactive gas characterized by a musty odour. The most common form of this substance is hexafluoroacetone sesquihydrate (1.5 H2O), which is a hemihydrate of hexafluoropropane-2,2-diol , a geminal diol. Synthesis The industrial route to HFA involves treatment of hexachloroacetone with HF: :(CCl3)2CO + 6 HF → (CF3)2CO + 6 HCl Hexafluoropropylene oxide rearranges to give HFA. In the laboratory, HFA can be prepared in a two step process from perfluoropropene. In the first step KF catalyzes the reaction of the alkene with elemental sulfur to give the 1,3-dithietane CF3)2CSsub>2. This species is then oxidized by iodate to give (CF3)2CO. Uses Hexafluoroacetone is used in the production of hexafluoroisopropanol: :(CF3)2CO + H2 → (CF3)2CHOH It is also used as a precursor ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aminomethanol
Aminomethanol is the amino alcohol with the chemical formula of H2NCH2OH. With an amino group and an alcohol group on the same carbon atom, the compound is also an hemiaminal. In aqueous solution, methanolamine exists in equilibrium with formaldehyde and ammonia. It is an intermediate en route to hexamethylenetetramine Hexamethylenetetramine, also known as methenamine, hexamine, or urotropin, is a heterocyclic organic compound with the formula (CH2)6N4. This white crystalline compound is highly soluble in water and polar organic solvents. It has a cage-like s .... The reaction can be conducted in gas phase and in solution. References Primary alcohols Amines {{Amine-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methanolamine
Aminomethanol is the amino alcohol with the chemical formula of H2NCH2OH. With an amino group and an alcohol group on the same carbon atom, the compound is also an hemiaminal. In aqueous solution, methanolamine exists in equilibrium with formaldehyde and ammonia. It is an intermediate en route to hexamethylenetetramine Hexamethylenetetramine, also known as methenamine, hexamine, or urotropin, is a heterocyclic organic compound with the formula (CH2)6N4. This white crystalline compound is highly soluble in water and polar organic solvents. It has a cage-like s .... The reaction can be conducted in gas phase and in solution. References Primary alcohols Amines {{Amine-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Amino Alcohol
In organic chemistry, alkanolamines are organic compounds that contain both hydroxyl () and amino (, , and ) functional groups on an alkane backbone. The term alkanolamine is a broad class term that is sometimes used as a subclassification. Methanolamine.svg, methanolamine, an intermediate in the reaction of ammonia with formaldehyde Ethanolamine.png, Ethanolamine 2-amino-2-methyl-1-propanol.svg, 2-amino-2-methyl-1-propanol is a precursor to oxazolines valinol.svg, valinol is derived from the amino acid valine Sphingosine structure.svg, Sphingosine is a component of some cell membrane. 1-Aminoalcohols 1-Aminoalcohols are better known as hemiaminals. Methanolamine is the simplest member. 2-Aminoalcohols Key members: ethanolamine, dimethylethanolamine, ''N''-methylethanolamine, Aminomethyl propanol Two popular drugs, often called alkanolamine beta blockers, are members of this structural class: propranolol, pindolol. Isoetarine is yet another medicinally useful derivative o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
1,3,5-Trimethyl-1,3,5-triazacyclohexane
1,3,5-Trimethyl-1,3,5-triazacyclohexane is an organic compound with the formula (CHNCH). It is a colorless liquid that is soluble in many organic solvents. Structurally, it is one of several related hexahydro-1,3,5-triazines, which typically result from the condensation reaction of amines and formaldehyde. It undergoes deprotonation by butyllithium Butyllithium may refer to one of 5 isomeric organolithium reagents of which 3 are commonly used in chemical synthesis: * ''n''-Butyllithium, abbreviated BuLi or nBuLi * ''sec''-Butyllithium, abbreviated ''sec''-BuLi or sBuLi, has 2 stereoisomers, ... to give a reagent that serves as a source of the formyl anion.V. Subramanian "1,3,5-Trimethyl-1,3,5-triazacyclohexane " e-EROS Encyclopedia of Reagents for Organic Synthesis 2007. References {{DEFAULTSORT:Trimethyl-1, 3, 5-triazacyclohexane, 1, 3, 5- Amines Triazines ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bis(dimethylamino)methane
Bis(dimethylamino)methane is the organic compound with the formula CH3)2Nsub>2CH2. It is classified as an aminal as well as a ditertiary amine, in fact the simplest. It is a colorless liquid that is widely available. It is prepared by the reaction of dimethylamine and formaldehyde Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...: : 2 (CH3)2NH + CH2O → CH3)2Nsub>2CH2 + H2O It is used for the dimethyl aminomethylation reactions, the reaction being initiated by the addition of a strong, anhydrous acid:{{cite journal , journal=eEROS, Encyclopedia of Reagents for Organic Synthesis, title=Bis(dimethylamino)methane, doi=10.1002/047084289X.rb143, author=Allen J. Duplantier : CH3)2Nsub>2CH2 + H+ → (CH3)2NCH2+ + (CH3)2NH Related reagents * N,N,N′,N′-Tetramethylfo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Formaldehyde
Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section Forms below), hence it is stored as an aqueous solution (formalin), which is also used to store animal specimens. It is the simplest of the aldehydes (). The common name of this substance comes from its similarity and relation to formic acid. Formaldehyde is an important precursor to many other materials and chemical compounds. In 1996, the installed capacity for the production of formaldehyde was estimated at 8.7 million tons per year. It is mainly used in the production of industrial resins, e.g., for particle board and coatings. Forms Formaldehyde is more complicated than many simple carbon compounds in that it adopts several diverse forms. These compounds can often be used interchangeably and can be interconverted. *Molecular formald ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydroxyl
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy groups. Both the negatively charged anion , called hydroxide, and the neutral radical , known as the hydroxyl radical, consist of an unbonded hydroxy group. According to IUPAC definitions, the term ''hydroxyl'' refers to the hydroxyl radical () only, while the functional group is called a ''hydroxy group''. Properties Water, alcohols, carboxylic acids, and many other hydroxy-containing compounds can be readily deprotonated due to a large difference between the electronegativity of oxygen (3.5) and that of hydrogen (2.1). Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack this f ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
