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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...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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...
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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(E)-4-Bromo-2-[(2-hydroxy-phen-yl)iminiometh-yl]phenolate.

Naser Eltaher Eltayeb, Siang Guan Teoh, Hoong-Kun Fun

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

    This study details the crystal structure of a zwitterionic compound, revealing a near-planar trans configuration. Intramolecular hydrogen bonds form an S(6) ring, while intermolecular interactions create a 2D network.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Solid-State Chemistry

    Background:

    • Zwitterions are neutral molecules with both positive and negative formal charges.
    • Understanding crystal packing and intermolecular interactions is crucial for material properties.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(13)H(10)BrNO(2).
    • To investigate the molecular geometry, hydrogen bonding, and crystal packing of the zwitterionic form.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed.
    • The crystal structure was solved and refined, including analysis of bond distances, angles, and intermolecular contacts.
    • Twin crystal analysis was performed.

    Main Results:

    • The compound crystallizes as a zwitterion in a trans configuration, exhibiting near planarity (dihedral angle 2.29°).
    • An intramolecular N-H⋯O hydrogen bond forms an S(6) ring motif.
    • Intermolecular O-H⋯O hydrogen bonds link molecules into chains, further connected by C-H⋯Br interactions into a 2D network.

    Conclusions:

    • The crystal structure reveals specific hydrogen bonding patterns and network formation in the solid state.
    • The observed short C⋯C and C⋯Br contacts provide insights into intermolecular forces.
    • The compound exhibits complex crystal packing driven by electrostatic and van der Waals interactions.