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
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DOI - Digital Object Identifier
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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
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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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
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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
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UT code for WoS article
000275084400062
EID of the result in the Scopus database
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