Electrochemical Cleavage of Carbon-Chlorine Bonds in Multiply Bridge-Chlorinated Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acids
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F21%3A00545682" target="_blank" >RIV/61388955:_____/21:00545682 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/21:00543194
Result on the web
<a href="http://hdl.handle.net/11104/0322353" target="_blank" >http://hdl.handle.net/11104/0322353</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/celc.202100372" target="_blank" >10.1002/celc.202100372</a>
Alternative languages
Result language
angličtina
Original language name
Electrochemical Cleavage of Carbon-Chlorine Bonds in Multiply Bridge-Chlorinated Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acids
Original language description
Reduction of five derivatives of bicyclo[1.1.1]pentane-1,3-dicarboxylic acid containing one to four chlorine substituents on methylene bridges were investigated by cyclic voltammetry and electrochemical impedance spectroscopy. Electrochemical cleavage of C-Cl bonds and the reduction of H+ provided by dissociation of COOH groups are two competing processes characterized by different time constants. A concerted mechanism of C-Cl bonds cleavage is operative. The location of LUMO orbitals changes with increasing number of chlorine substituents from COOH sites to bicyclo[1.1.1]pentane. Carboxylic groups participate in the protonation of intermediates formed by the C-Cl bond rupture. The esterification of two derivatives eliminates the self-protonation. Esters are reduced only at very negative potentials near the end of an available potential window.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10405 - Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis)
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ChemElectroChem
ISSN
2196-0216
e-ISSN
2196-0216
Volume of the periodical
8
Issue of the periodical within the volume
17
Country of publishing house
DE - GERMANY
Number of pages
7
Pages from-to
3243-3249
UT code for WoS article
000655723400001
EID of the result in the Scopus database
2-s2.0-85106600032