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Related Concept Videos

E2 Reaction: Kinetics and Mechanism02:45

E2 Reaction: Kinetics and Mechanism

SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
E2 Reaction: Stereochemistry and Regiochemistry02:43

E2 Reaction: Stereochemistry and Regiochemistry

Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the regiochemistry of the reaction governs the location of the double bond in the product, the stereochemical requirements often influence the geometry.
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major product and...
Phase II Reactions: Methylation Reactions01:17

Phase II Reactions: Methylation Reactions

Methylation is a phase II biotransformation process involving the attachment of a methyl group to a substrate. Enzymes known as methyltransferases orchestrate this reaction.
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...
Amines to Alkenes: Hofmann Elimination01:16

Amines to Alkenes: Hofmann Elimination

Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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(E)-2-[(2-Hydroxy-ethyl)iminiometh-yl]-6-methoxy-phenolate.

Guo-Xia Tan, Xi-Cheng Liu

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary
    This summary is machine-generated.

    This study details the zwitterionic crystal structure of a novel Schiff base compound, C(10)H(13)NO(3), revealing intramolecular hydrogen bonding and intermolecular chain formation in its solid state.

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    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Supramolecular Chemistry

    Background:

    • Schiff bases are versatile organic compounds with diverse applications.
    • Understanding the solid-state structure of Schiff bases is crucial for predicting their properties and designing new materials.
    • Zwitterionic forms in organic molecules can lead to unique electronic and physical characteristics.

    Purpose of the Study:

    • To synthesize and characterize a novel Schiff base compound, C(10)H(13)NO(3).
    • To elucidate the crystal structure of the synthesized Schiff base, focusing on its molecular conformation and intermolecular interactions.
    • To investigate the presence and role of hydrogen bonding in the crystal packing.

    Main Methods:

    • Synthesis of the Schiff base via condensation reaction between 2-hydroxy-3-methoxy-benzaldehyde and 2-amino-ethanol in methanol.
    • Single-crystal X-ray diffraction analysis to determine the molecular and crystal structure.
    • Analysis of bond lengths, bond angles, and intermolecular interactions (hydrogen bonding).

    Main Results:

    • The Schiff base compound C(10)H(13)NO(3) was successfully synthesized and crystallized.
    • The compound crystallizes in a zwitterionic form, adopting a trans configuration around the central C=N bond.
    • An intramolecular N-H⋯O hydrogen bond was identified within the molecule.
    • Intermolecular O-H⋯O hydrogen bonding links the molecules into chains in the crystal lattice.

    Conclusions:

    • The synthesized Schiff base exhibits a zwitterionic structure in the solid state.
    • The observed trans configuration and intramolecular hydrogen bond contribute to the molecule's stability.
    • Intermolecular hydrogen bonding plays a significant role in the crystal packing, leading to the formation of extended chains.