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Related Concept Videos

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...

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2-(2-Hydroxy-ethyl)-3-[(2-hydroxy-ethyl)imino]isoindolin-1-one.

Jiří Urban, Jiří Ludvík, Jan Fábry

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    |May 18, 2011
    PubMed
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    This study reveals the crystal structure of C(12)H(14)N(2)O(3), detailing molecular packing into layers. Strong hydrogen bonds create dimers and a 2D network, stabilized by weaker interactions and π-π stacking.

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    Area of Science:

    • Crystallography
    • Supramolecular Chemistry
    • Materials Science

    Background:

    • Understanding molecular interactions is crucial for designing novel materials.
    • Crystal engineering relies on predicting and controlling intermolecular forces.
    • The title compound, C(12)H(14)N(2)O(3), presents an opportunity to study complex hydrogen bonding networks.

    Purpose of the Study:

    • To elucidate the crystal structure of the title compound, C(12)H(14)N(2)O(3).
    • To analyze the hydrogen bonding network and supramolecular assembly.
    • To investigate the role of weak interactions in crystal stabilization.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional crystal structure.
    • Analysis of hydrogen bonding patterns using geometric criteria.
    • Investigation of π-π stacking interactions and their contribution to the crystal lattice.

    Main Results:

    • The crystal structure reveals molecules arranged in layers parallel to the (100) plane.
    • Centrosymmetric dimers linked by O-H⋯N hydrogen bonds (R(2)(2)(10) motif) were identified.
    • A two-dimensional network is formed via O-H⋯O hydrogen bonds (C(10) chains).
    • Weak C-H⋯O interactions and π-π stacking (3.4220(7)-3.9616(7) Å) further stabilize the structure.

    Conclusions:

    • The crystal structure of C(12)H(14)N(2)O(3) exhibits a complex, layered arrangement driven by strong hydrogen bonding.
    • The interplay of strong and weak interactions dictates the formation of a stable two-dimensional supramolecular network.
    • This detailed structural analysis provides insights into crystal packing principles and potential applications in materials design.