Aminoferrocene:Determination of the acidity of unstable
compounds

D 2019

Aminoferrocene:Determination of the acidity of unstable compounds

VĚŽNÍK, Jakub, Libuše TRNKOVÁ a Karel LACINA

Základní údaje

Originální název

Aminoferrocene:Determination of the acidity of unstable compounds

Autoři

VĚŽNÍK, Jakub (203 Česká republika, domácí), Libuše TRNKOVÁ (203 Česká republika, domácí) a Karel LACINA (203 Česká republika, garant, domácí)

Vydání

1. vyd. Brno, XIX. Workshop of Biophysical Chemists and Electrochemists, od s. 34-35, 2 s. 2019

Nakladatel

Masarykova univerzita

Další údaje

Jazyk

angličtina

Typ výsledku

Stať ve sborníku

Obor

10405 Electrochemistry

Stát vydavatele

Česká republika

Utajení

není předmětem státního či obchodního tajemství

Forma vydání

elektronická verze "online"

Kód RIV

RIV/00216224:14310/19:00110349

Organizační jednotka

Přírodovědecká fakulta

ISBN

978-80-210-9309-6

Klíčová slova anglicky

aminoferrocene; electrochemistry; gold electrode; platinum electrode; glassy carbon electrode; boron doped diamond electrode; pKa constants

Změněno: 9. 8. 2019 09:45, RNDr. Mgr. Iveta Třísková, Ph.D.

Anotace

V originále

Ferrocenes are quite popular in electrochemistry, due to the simplicity of redox reactions of iron core. While ferrocene is nonpolar and thus of limited use, its cyclopentadienyl ring opens way for many interesting modifications. One of which is aminoferrocene (FcNH2), the -NH2 group increases solubility in polar solvents, introduces chemical reactivity and most importantly pH sensitivity to the ferrocene complex. Due to the proximity of NH2 group and Fe2+ ion in FcNH2, the redox potential of FcNH2 is influenced by protonation and vice versa the Fe3+ ion changes acidity of the complex upon oxidation. Electrochemical observation of this interplay can be used to deduce the acidity of the Fe3+ complex. Such approach is useful for complexes that are unstable in their oxidized form. pKa constants determined using electrochemical methods are obtained through kinetic processes, therefore great care needs to be taken when interpreting these results. While the limiting redox potential for FcNH2 is easily obtained from electrochemical results (Figure), the limiting potential for FcNH3+ strongly varies depending on the type of electrode used. This is anomalous from other ferrocene derivates, namely ferroceneboronic acid [1] and ferrocenecarboxylic acid [2], where both limiting redox potentials are easily obtainable. In our contribution, we tried to uncover the correct pKa value of aminoferrocene through different electrochemical methods both in buffered and unbuffered solutions. Spectrophotometry was used along to validate our findings.

Návaznosti

LQ1601, projekt VaV

Název: CEITEC 2020 (Akronym: CEITEC2020)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, CEITEC 2020

MUNI/A/1359/2018, interní kód MU

Název: Vývoj metod a instrumentace pro analýzu biologicky významných látek 2019

Investor: Masarykova univerzita, Vývoj metod a instrumentace pro analýzu biologicky významných látek 2019, DO R. 2020_Kategorie A - Specifický výzkum - Studentské výzkumné projekty

Citovat

VĚŽNÍK, Jakub, Libuše TRNKOVÁ a Karel LACINA. Aminoferrocene:Determination of the acidity of unstable compounds. Online. In Libuše Trnková. XIX. Workshop of Biophysical Chemists and Electrochemists. 1. vyd. Brno: Masarykova univerzita, 2019, s. 34-35. ISBN 978-80-210-9309-6.

@inproceedings{1548842,
   author = {Věžník, Jakub and Trnková, Libuše and Lacina, Karel},
   address = {Brno},
   booktitle = {XIX. Workshop of Biophysical Chemists and Electrochemists},
   edition = {1},
   editor = {Libuše Trnková},
   keywords = {aminoferrocene; electrochemistry; gold electrode; platinum electrode; glassy carbon electrode; boron doped diamond electrode; pKa constants},
   howpublished = {elektronická verze "online"},
   language = {eng},
   location = {Brno},
   isbn = {978-80-210-9309-6},
   pages = {34-35},
   publisher = {Masarykova univerzita},
   title = {Aminoferrocene:Determination of the acidity of unstable compounds},
   year = {2019}
}

TY  - JOUR
ID  - 1548842
AU  - Věžník, Jakub - Trnková, Libuše - Lacina, Karel
PY  - 2019
TI  - Aminoferrocene:Determination of the acidity of unstable compounds
PB  - Masarykova univerzita
CY  - Brno
SN  - 9788021093096
KW  - aminoferrocene
KW  - electrochemistry
KW  - gold electrode
KW  - platinum electrode
KW  - glassy carbon electrode
KW  - boron doped diamond electrode
KW  - pKa constants
N2  - Ferrocenes are quite popular in electrochemistry, due to the simplicity of redox reactions of iron core. While ferrocene is nonpolar and thus of limited use, its cyclopentadienyl ring opens way for many interesting modifications. One of which is aminoferrocene (FcNH2), the -NH2 group increases solubility in polar solvents, introduces chemical reactivity and most importantly pH sensitivity to the ferrocene complex. Due to the proximity of NH2 group and Fe2+ ion in FcNH2, the redox potential of FcNH2 is influenced by protonation and vice versa the Fe3+ ion changes acidity of the complex upon oxidation. Electrochemical observation of this interplay can be used to deduce the acidity of the Fe3+ complex. Such approach is useful for complexes that are unstable in their oxidized form. pKa constants determined using electrochemical methods are obtained through kinetic processes, therefore great care needs to be taken when interpreting these results. While the limiting redox potential for FcNH2 is easily obtained from electrochemical results (Figure), the limiting potential for FcNH3+ strongly varies depending on the type of electrode used. This is anomalous from other ferrocene derivates, namely ferroceneboronic acid [1] and ferrocenecarboxylic acid [2], where both limiting redox potentials are easily obtainable. In our contribution, we tried to uncover the correct pKa value of aminoferrocene through different electrochemical methods both in buffered and unbuffered solutions. Spectrophotometry was used along to validate our findings.
ER  -

VĚŽNÍK, Jakub, Libuše TRNKOVÁ a Karel LACINA. Aminoferrocene:Determination of the acidity of unstable compounds. Online. In Libuše Trnková. \textit{XIX. Workshop of Biophysical Chemists and Electrochemists}. 1. vyd. Brno: Masarykova univerzita, 2019, s.~34-35. ISBN~978-80-210-9309-6.

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