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Azomethine Ylide
Azomethine ylides are nitrogen-based 1,3-dipoles, consisting of an iminium ion next to a carbanion. They are used in 1,3-dipolar cycloaddition reactions to form five-membered heterocycles, including pyrrolidines and pyrrolines. These reactions are highly stereoselectivity, stereo- and regioselective, and have the potential to form four new contiguous stereocenters. Azomethine ylides thus have high utility in total synthesis, and formation of chiral ligands and pharmaceuticals. Azomethine ylides can be generated from many sources, including aziridines, imines, and iminiums. They are often generated ''in situ'', and immediately reacted with dipolarophiles. Structure The resonance structures below show the 1,3-dipole contribution, in which the two carbon atoms adjacent to the nitrogen have a negative or positive charge. The most common representation of azomethine ylides is that in which the nitrogen is positively charged, and the negative charge is shared between the two carbon ato ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Azomethine Ylide 2
In organic chemistry, a Schiff base (named after Hugo Schiff) is a compound with the general structure ( = alkyl or aryl, but not hydrogen). They can be considered a sub-class of imines, being either secondary ketimines#Nomenclature and classification, ketimines or secondary ketimines#Nomenclature and classification, aldimines depending on their structure. Anil refers to a common subset of Schiff bases: imines derived from anilines. The term can be synonymous with azomethine which refers specifically to secondary aldimines (i.e. where R' ≠ H). Synthesis Schiff bases can be synthesized from an aliphatic amine, aliphatic or aromatic amine and a carbonyl compound by nucleophilic addition forming a hemiaminal, followed by a dehydration reaction, dehydration to generate an imine. In a typical reaction, 4,4'-oxydianiline reacts with ''o''-vanillin: Schiff bases can also be synthesized via the Aza-Wittig reaction. Biochemistry Schiff bases have been investigated in relatio ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Deprotonation
Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen cation), (H+) from a Brønsted–Lowry acid in an acid–base reaction.Henry Jakubowski, Biochemistry Online Chapter 2A3, https://employees.csbsju.edu/hjakubowski/classes/ch331/protstructure/PS_2A3_AA_Charges.html, accessed 12/2/2020 The species formed is the conjugate base of that acid. The complementary process, when a proton is added (transferred) to a Brønsted–Lowry base, is protonation (or hydronation). The species formed is the conjugate acid of that base. A species that can either accept or donate a proton is referred to as amphiprotic. An example is the H2O (water) molecule, which can gain a proton to form the hydronium ion, H3O+, or lose a proton, leaving the hydroxide ion, OH−. The relative ability of a molecule to give up a proton is measured by its p''K''a value. A low p''K''a value indicates that the compound is acidic and will easily give up its proton to a base ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distinctive functional group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well (e.g. amides), but not according to the IUPAC. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Lactones are cyclic carboxylic esters; naturally occurring lactones are mainly 5- and 6-membered ring lactones. Lactones contribute to the aroma of fruits, butter, cheese, vegetables like celery and other foods. Esters can be formed from oxoacids (e.g. esters of acetic acid, carbonic acid ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Amine
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of electrons. Amines can also exist as hetero cyclic compounds. Aniline is the simplest aromatic amine, consisting of a benzene ring bonded to an amino group. Amines are classified into three types: primary (1°), secondary (2°), and tertiary (3°) amines. Primary amines (1°) contain one alkyl or aryl substituent and have the general formula RNH2. Secondary amines (2°) have two alkyl or aryl groups attached to the nitrogen atom, with the general formula R2NH. Tertiary amines (3°) contain three substituent groups bonded to the nitrogen atom, and are represented by the formula R3N. The functional group present in primary amines is called the amino group. Classification of amines Amines can be classified according to the nature and number o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aldehyde
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology. Structure and bonding Aldehyde molecules have a central carbon atom that is connected by a double bond to oxygen, a single bond to hydrogen and another single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen. The central carbon is often described as being sp2- hybridized. The aldehyde group is somewhat polar. The bond length is about 120–122 picometers. Physical properties and characterization Aldehydes have properties that are diverse and that depend on the remainder of the molecule. Smaller aldehydes such as formaldehyde and acetaldehyde are solubl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Azomethine Ylide From Condensation
In organic chemistry, a Schiff base (named after Hugo Schiff) is a compound with the general structure ( = alkyl or aryl, but not hydrogen). They can be considered a sub-class of imines, being either secondary ketimines or secondary aldimines depending on their structure. Anil refers to a common subset of Schiff bases: imines derived from anilines. The term can be synonymous with azomethine which refers specifically to secondary aldimines (i.e. where R' ≠ H). Synthesis Schiff bases can be synthesized from an aliphatic or aromatic amine and a carbonyl compound by nucleophilic addition forming a hemiaminal, followed by a dehydration to generate an imine. In a typical reaction, 4,4'-oxydianiline reacts with ''o''-vanillin: Schiff bases can also be synthesized via the Aza-Wittig reaction. Biochemistry Schiff bases have been investigated in relation to a wide range of contexts, including antimicrobial, antiviral and anticancer activity. They have also been considered f ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Torquoselectivity
In stereochemistry, torquoselectivity is a special kind of stereoselectivity observed in electrocyclic reactions, defined as "the preference for inward or outward rotation of substituents in conrotatory or disrotatory electrocyclic reactions." Torquoselectivity is not to be confused with the normal diastereoselectivity seen in pericyclic reactions, as it represents a further level of selectivity beyond the Woodward-Hoffman rules. The name derives from the idea that the substituents in an electrocyclization appear to rotate over the course of the reaction, and thus selection of a single product is equivalent to selection of one direction of rotation (i.e. the direction of torque on the substituents). The concept was originally developed by American chemist Kendall N. Houk. For ring closing reactions, it is an example of enantioselectivity, wherein a single enantiomer of a cyclization product is formed from the selective ring closure of the starting material. In a typical electroc ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aziridine Opening
Aziridine is an organic compound consisting of the three-membered heterocycle . It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivatives, also referred to as aziridines, are of broader interest in medicinal chemistry. Structure The bond angles in aziridine are approximately 60°, considerably less than the normal hydrocarbon bond angle of 109.5°, which results in angle strain as in the comparable cyclopropane and ethylene oxide molecules. A banana bond model explains bonding in such compounds. Aziridine is less basic than acyclic aliphatic amines, with a pKa of 7.9 for the conjugate acid, due to increased s character of the nitrogen free electron pair. Angle strain in aziridine also increases the barrier to nitrogen inversion. This barrier height permits the isolation of separate ''invertomers'', for example the ''cis'' and ''trans'' invertomers of ''N''-chloro- ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Conrotatory And Disrotatory
In organic chemistry, an electrocyclic reaction can either be classified as conrotatory or disrotatory based on the rotation at each end of the molecule. In conrotatory mode, both atomic orbitals of the end groups turn in the same direction (such as both atomic orbitals rotating clockwise or counter-clockwise). In disrotatory mode, the atomic orbitals of the end groups turn in opposite directions (one atomic orbital turns clockwise and the other counter-clockwise). The cis/trans geometry of the final product is directly decided by the difference between conrotation and disrotation. Determining whether a particular reaction is conrotatory or disrotatory can be accomplished by examining the molecular orbitals of each molecule and through a set of rules. Only two pieces of information are required to determine conrotation or disrotation using the set of rules: how many electrons are in the pi-system and whether the reaction is induced by heat or by light. This set of rules can a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Woodward–Hoffmann Rules
The Woodward–Hoffmann rules (or the pericyclic selection rules) are a set of rules devised by Robert Burns Woodward and Roald Hoffmann to rationalize or predict certain aspects of the stereochemistry and activation energy of Pericyclic reaction, pericyclic reactions, an important class of reactions in organic chemistry. The rules originate in certain symmetries of the Molecular orbital, molecule's orbital structure that any molecular Hamiltonian Conserved quantity, conserves. Consequently, any symmetry-violating reaction must Coupling (physics), couple extensively to Thermal bath (thermodynamics), the environment; this imposes an energy barrier on its occurrence, and such reactions are called symmetry-forbidden. Their opposites are symmetry-allowed. Although the symmetry-imposed barrier is often formidable (up to ca. 5 eV or 480 kJ/mol in the case of a forbidden [2+2] cycloaddition), the prohibition is not absolute, and symmetry-forbidden reactions can still take place if other ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Journal Of The American Chemical Society
The ''Journal of the American Chemical Society'' (also known as JACS) is a weekly peer-reviewed scientific journal that was established in 1879 by the American Chemical Society. The journal has absorbed two other publications in its history, the ''Journal of Analytical and Applied Chemistry'' (July 1893) and the ''American Chemical Journal'' (January 1914). It covers all fields of chemistry. Since 2021, the editor-in-chief is Erick M. Carreira (ETH Zurich). In 2014, the journal moved to a hybrid open access publishing model. Abstracting and indexing The journal is abstracted and indexed in: According to the ''Journal Citation Reports'', the journal has a 2023 impact factor The impact factor (IF) or journal impact factor (JIF) of an academic journal is a type of journal ranking. Journals with higher impact factor values are considered more prestigious or important within their field. The Impact Factor of a journa ... of 14.4. Editors-in-chief The following people are or ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
