Počet záznamů: 1
Electrochemical Cleavage of Carbon-Chlorine Bonds in Multiply Bridge-Chlorinated Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acids
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SYSNO ASEP 0543194 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Electrochemical Cleavage of Carbon-Chlorine Bonds in Multiply Bridge-Chlorinated Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acids Tvůrce(i) Kaleta, Jiří (UOCHB-X) RID, ORCID
Hromadová, M. (CZ)
Pospíšil, Lubomír (UOCHB-X) RID, ORCIDZdroj.dok. ChemElectroChem. - : Wiley - ISSN 2196-0216
Roč. 8, č. 17 (2021), s. 3243-3249Poč.str. 7 s. Jazyk dok. eng - angličtina Země vyd. DE - Německo Klíč. slova bicyclo[1.1.1]pentane-1,3-dicarboxylic acids ; C−Cl cleavage ; protonation ; reduction ; voltammetry Obor OECD Organic chemistry CEP GX20-03691X GA ČR - Grantová agentura ČR GA20-13745S GA ČR - Grantová agentura ČR Způsob publikování Omezený přístup Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000655723400001 EID SCOPUS 85106600032 DOI 10.1002/celc.202100372 Anotace 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. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Rok sběru 2022 Elektronická adresa https://doi.org/10.1002/celc.202100372
Počet záznamů: 1