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Naphthol Coupling Monitored by Infrared Spectroscopy in the Gas Phase

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F10%3A10062551" target="_blank" >RIV/00216208:11310/10:10062551 - isvavai.cz</a>

  • Alternative codes found

    RIV/61388963:_____/10:00353570

  • Result on the web

  • DOI - Digital Object Identifier

Alternative languages

  • Result language

    angličtina

  • Original language name

    Naphthol Coupling Monitored by Infrared Spectroscopy in the Gas Phase

  • Original language description

    The reaction mechanism of copper(II)-mediated naphthol coupling in the presence of TMEDA (N,N,N',N'-tetramethylethylenediamine) is studied using infrared multiphoton dissociation (IRMPD) spectroscopy and DFT calculations. It is shown that the coupling reaction proceeds in ad hoc formed binuclear clusters [(1-H)(2)Cu2Cl(TMEDA)(2)](+), where (1-H) is a deprotonated naphthol molecule (methyl ester of 3-hydroxy-2-naphthoic acid). The IRMPD spectra of the isolated cluster in the gas phase reveal that it contains two uncoupled naphtholate subunits and only the irradiation promotes the coupling reaction, which is thus observed as a genuine gas-phase reaction. The driving force for the C-C coupling is a keto-enol tautomerization of the initial coupling product, and the formation of the corresponding binol in the cluster is exothermic by 0.61 eV. In contrast, analogous C-O and O-O couplings are endothermic reactions.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

  • CEP classification

    CC - Organic chemistry

  • OECD FORD branch

Result continuities

  • Project

    <a href="/en/project/KJB400550704" target="_blank" >KJB400550704: Intrinsic properties of redox-active molecules</a><br>

  • Continuities

    Z - Vyzkumny zamer (s odkazem do CEZ)<br>S - Specificky vyzkum na vysokych skolach

Others

  • Publication year

    2010

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Journal of the American Chemical Society

  • ISSN

    0002-7863

  • e-ISSN

  • Volume of the periodical

    132

  • Issue of the periodical within the volume

    1

  • Country of publishing house

    US - UNITED STATES

  • Number of pages

    8

  • Pages from-to

  • UT code for WoS article

    000275084400062

  • EID of the result in the Scopus database