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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.
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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.
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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

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(E)-4-Allyl-2-[(2-hydroxy-phen-yl)iminiometh-yl]-6-methoxy-phenolate.

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    PubMed
    Summary

    This study details the crystal structure of a zwitterionic compound, C(17)H(17)NO(3). The molecule features iminium and enolate groups in a trans configuration, with specific dihedral angles and hydrogen bonding interactions observed in its crystalline form.

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    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • Zwitterionic compounds exhibit unique chemical properties due to their internal charge separation.
    • Understanding molecular conformation and intermolecular interactions is crucial for predicting material properties.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(17)H(17)NO(3).
    • To characterize the zwitterionic nature, molecular geometry, and intermolecular interactions in the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction analysis was employed.
    • Detailed analysis of bond lengths, bond angles, dihedral angles, and hydrogen bonding networks.

    Main Results:

    • The compound crystallizes as a zwitterion with distinct iminium and enolate functionalities.
    • A trans configuration around the C=N bond and specific dihedral angles between aromatic rings and substituents were determined.
    • Intramolecular N-H⋯O hydrogen bonding formed an S(6) ring, and intermolecular O-H⋯O bonds created zigzag chains.

    Conclusions:

    • The crystal structure reveals a well-defined molecular architecture with significant intra- and intermolecular interactions.
    • The observed hydrogen bonding and π-interactions influence the packing and stability of the zwitterionic compound in the solid state.