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Related Concept Videos

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...
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
Benzene to Phenol via Cumene: Hock Process01:27

Benzene to Phenol via Cumene: Hock Process

The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene hydroperoxide...
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Amines to Alkenes: Cope Elimination01:14

Amines to Alkenes: Cope Elimination

Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

(E)-4-Methyl-2-{[tris(hydroxymethyl)methyl]iminiomethyl}phenolate.

Gonca Ozdemir Tarı, Hasan Tanak, Mustafa Macit

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

    The zwitterionic compound C(12)H(17)NO(4) features an internal hydrogen bond forming a six-membered ring. Intermolecular interactions further stabilize the crystal structure.

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    Area of Science:

    • Crystallography
    • Chemical Physics
    • Materials Science

    Background:

    • Zwitterionic compounds exhibit unique chemical properties due to their charge distribution.
    • Hydrogen bonding plays a crucial role in molecular self-assembly and crystal engineering.
    • Understanding crystal structures provides insights into intermolecular forces and material properties.

    Purpose of the Study:

    • To characterize the crystal structure of the zwitterionic compound C(12)H(17)NO(4).
    • To investigate the role of intra-molecular and inter-molecular hydrogen bonding in its solid-state arrangement.
    • To elucidate the factors governing the formation of specific ring structures within the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular and crystal structure.
    • Analysis of hydrogen bonding networks, including intra-molecular and inter-molecular interactions.
    • Topological analysis of the hydrogen-bonded ring system (S(6)).

    Main Results:

    • The crystal structure reveals a zwitterionic molecule with the chemical formula C(12)H(17)NO(4).
    • An intra-molecular N-H⋯O hydrogen bond was identified, forming a stable six-membered ring (S(6)).
    • Inter-molecular interactions, specifically C-H⋯O and O-H⋯O bonds, link molecules into a cohesive crystal lattice.

    Conclusions:

    • The study successfully determined the crystal structure of the title zwitterionic compound.
    • Intra-molecular hydrogen bonding is a key feature dictating the local conformation.
    • Intermolecular interactions are essential for the overall crystal packing and stability.