Crystal structure and geometry-optimization study of 2-benzyliminiomethylene-4-nitrophenolate

Biplab Mondal, Goutam Kumar Lahiri, Pance Naumov, Seik Weng Ng

    Research output: Contribution to journalArticle

    Abstract

    5-Nitro-2-hydroxybenzaldehyde condenses with benzylamine to yield a Schiff base that exists in the solid state as zwitterionic form as 2-benzyliminiomethylene-4-nitrophenolate. In the crystal structure, two zwitterions are linked together as a centrosymmetric dimer by hydrogen bonds involving the iminium hydrogen atom [N···Ointramonomer = 2.653(2), N···Ointradimer = 2.880(12) Å]. Geometry-optimizations on the monomeric zwitterion and the isomeric hypothetical 2-benzyliminomethylene-4-nitrophenol molecule by the B3LYP/6-31++G(d,p) method imply an endothermic process [ΔH = 12.4 kcal mol-1] for the transfer of the phenolic proton in the hypothetical neutral molecule to furnish the zwitterionic molecule.

    Original languageEnglish (US)
    Pages (from-to)131-135
    Number of pages5
    JournalJournal of Molecular Structure
    Volume613
    Issue number1-3
    DOIs
    StatePublished - Aug 1 2002

    Fingerprint

    Hydrogen
    zwitterions
    Crystal structure
    crystal structure
    Molecules
    optimization
    Schiff Bases
    Geometry
    geometry
    Protons
    molecules
    Dimers
    imines
    hydrogen atoms
    Hydrogen bonds
    dimers
    hydrogen bonds
    solid state
    Atoms
    protons

    Keywords

    • 2-Benzyliminiomethylene-4-nitrophenolate
    • Crystal structure
    • Geometry-optimization
    • Hydrogen bonding
    • Zwitterion

    ASJC Scopus subject areas

    • Structural Biology
    • Organic Chemistry
    • Physical and Theoretical Chemistry
    • Spectroscopy
    • Atomic and Molecular Physics, and Optics

    Cite this

    Crystal structure and geometry-optimization study of 2-benzyliminiomethylene-4-nitrophenolate. / Mondal, Biplab; Lahiri, Goutam Kumar; Naumov, Pance; Ng, Seik Weng.

    In: Journal of Molecular Structure, Vol. 613, No. 1-3, 01.08.2002, p. 131-135.

    Research output: Contribution to journalArticle

    Mondal, Biplab ; Lahiri, Goutam Kumar ; Naumov, Pance ; Ng, Seik Weng. / Crystal structure and geometry-optimization study of 2-benzyliminiomethylene-4-nitrophenolate. In: Journal of Molecular Structure. 2002 ; Vol. 613, No. 1-3. pp. 131-135.
    @article{d1ebf3e893a04a30af15e6bee3fbcba7,
    title = "Crystal structure and geometry-optimization study of 2-benzyliminiomethylene-4-nitrophenolate",
    abstract = "5-Nitro-2-hydroxybenzaldehyde condenses with benzylamine to yield a Schiff base that exists in the solid state as zwitterionic form as 2-benzyliminiomethylene-4-nitrophenolate. In the crystal structure, two zwitterions are linked together as a centrosymmetric dimer by hydrogen bonds involving the iminium hydrogen atom [N···Ointramonomer = 2.653(2), N···Ointradimer = 2.880(12) {\AA}]. Geometry-optimizations on the monomeric zwitterion and the isomeric hypothetical 2-benzyliminomethylene-4-nitrophenol molecule by the B3LYP/6-31++G(d,p) method imply an endothermic process [ΔH = 12.4 kcal mol-1] for the transfer of the phenolic proton in the hypothetical neutral molecule to furnish the zwitterionic molecule.",
    keywords = "2-Benzyliminiomethylene-4-nitrophenolate, Crystal structure, Geometry-optimization, Hydrogen bonding, Zwitterion",
    author = "Biplab Mondal and Lahiri, {Goutam Kumar} and Pance Naumov and Ng, {Seik Weng}",
    year = "2002",
    month = "8",
    day = "1",
    doi = "10.1016/S0022-2860(02)00132-1",
    language = "English (US)",
    volume = "613",
    pages = "131--135",
    journal = "Journal of Molecular Structure",
    issn = "0022-2860",
    publisher = "Elsevier",
    number = "1-3",

    }

    TY - JOUR

    T1 - Crystal structure and geometry-optimization study of 2-benzyliminiomethylene-4-nitrophenolate

    AU - Mondal, Biplab

    AU - Lahiri, Goutam Kumar

    AU - Naumov, Pance

    AU - Ng, Seik Weng

    PY - 2002/8/1

    Y1 - 2002/8/1

    N2 - 5-Nitro-2-hydroxybenzaldehyde condenses with benzylamine to yield a Schiff base that exists in the solid state as zwitterionic form as 2-benzyliminiomethylene-4-nitrophenolate. In the crystal structure, two zwitterions are linked together as a centrosymmetric dimer by hydrogen bonds involving the iminium hydrogen atom [N···Ointramonomer = 2.653(2), N···Ointradimer = 2.880(12) Å]. Geometry-optimizations on the monomeric zwitterion and the isomeric hypothetical 2-benzyliminomethylene-4-nitrophenol molecule by the B3LYP/6-31++G(d,p) method imply an endothermic process [ΔH = 12.4 kcal mol-1] for the transfer of the phenolic proton in the hypothetical neutral molecule to furnish the zwitterionic molecule.

    AB - 5-Nitro-2-hydroxybenzaldehyde condenses with benzylamine to yield a Schiff base that exists in the solid state as zwitterionic form as 2-benzyliminiomethylene-4-nitrophenolate. In the crystal structure, two zwitterions are linked together as a centrosymmetric dimer by hydrogen bonds involving the iminium hydrogen atom [N···Ointramonomer = 2.653(2), N···Ointradimer = 2.880(12) Å]. Geometry-optimizations on the monomeric zwitterion and the isomeric hypothetical 2-benzyliminomethylene-4-nitrophenol molecule by the B3LYP/6-31++G(d,p) method imply an endothermic process [ΔH = 12.4 kcal mol-1] for the transfer of the phenolic proton in the hypothetical neutral molecule to furnish the zwitterionic molecule.

    KW - 2-Benzyliminiomethylene-4-nitrophenolate

    KW - Crystal structure

    KW - Geometry-optimization

    KW - Hydrogen bonding

    KW - Zwitterion

    UR - http://www.scopus.com/inward/record.url?scp=0036681446&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=0036681446&partnerID=8YFLogxK

    U2 - 10.1016/S0022-2860(02)00132-1

    DO - 10.1016/S0022-2860(02)00132-1

    M3 - Article

    VL - 613

    SP - 131

    EP - 135

    JO - Journal of Molecular Structure

    JF - Journal of Molecular Structure

    SN - 0022-2860

    IS - 1-3

    ER -