Unexpected structural distribution of electroactive
ortho-Iminoboronate in protic and aprotic solvents determined
using MS

a 2017

Unexpected structural distribution of electroactive ortho-Iminoboronate in protic and aprotic solvents determined using MS

KONHEFR, Martin, Karel LACINA, Monika SKRUTKOVÁ LANGMAJEROVÁ, Zdeněk GLATZ, Petr SKLÁDAL et. al.

Základní údaje

Originální název

Unexpected structural distribution of electroactive ortho-Iminoboronate in protic and aprotic solvents determined using MS

Autoři

KONHEFR, Martin, Karel LACINA, Monika SKRUTKOVÁ LANGMAJEROVÁ, Zdeněk GLATZ, Petr SKLÁDAL a Ctibor MAZAL

Vydání

Book of Abstracts, CEITEC PhD Retreat II, 20-21 April 2017, Telč, Czech Republic, 2017

Další údaje

Jazyk

angličtina

Typ výsledku

Konferenční abstrakt

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

ISBN

978-80-210-8551-0

Klíčová slova česky

iminoboronát, ferocen, hmotnostní spektroskopie, kation, komplex

Klíčová slova anglicky

iminoboronate, ferrocene, mass spectroscopy, cation, complex

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 26. 1. 2018 08:25, prof. RNDr. Zdeněk Glatz, CSc.

Anotace

V originále

As metal cations are essential not only in biology, their selective sensing is important also from an industrial and environmental viewpoint. These diverse applications have lead to the development of many molecular sensor systems for cationic guest species. A wide variety of e. g. macrocycles with ferrocene unit as redox signaling group have been synthesized [1]. Generally, complexation by these ligands (cations) affects the electrochemistry of the redox center, particularly when the guest molecule is either in close proximity to the iron atom or coordinated by functional groups that are conjugated with the ferrocene system. This configuration is observable in the aminoferrocene derivatives. As we studied the structure of novel iminoboronates bearing ferrocene as a signaling group for electrochemical sensing intended for a saccharide recognition [2], we realized that ortho-positioned iminoboronate in MS formed stable sodium and potassium chelates. These complexation properties were observed only in a protic solvent (methanol). None complexes were detected in an aprotic solvent (acetonitrile). Thus, methanol–hydroxyle rearrangement on boron atom in the proximity of imino group plays the most important role in the forming of an ideal surrounding (host) around complexed cation (guest) to form the chelate. In addition, this interacting site is close to redox-active center of ferrocene which reports on the binding event. Contrary to the protic solvent, stable ortho-iminoboronate anhydrides were observed in the aprotic solvent without any tendency to form chelates with cations.

Návaznosti

LQ1601, projekt VaV

Název: CEITEC 2020 (Akronym: CEITEC2020)

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

MUNI/A/1278/2016, interní kód MU

Název: Podpora biochemického výzkumu v roce 2017

Investor: Masarykova univerzita, Podpora biochemického výzkumu v roce 2017, DO R. 2020_Kategorie A - Specifický výzkum - Studentské výzkumné projekty

Citovat

KONHEFR, Martin, Karel LACINA, Monika SKRUTKOVÁ LANGMAJEROVÁ, Zdeněk GLATZ, Petr SKLÁDAL a Ctibor MAZAL. Unexpected structural distribution of electroactive ortho-Iminoboronate in protic and aprotic solvents determined using MS. In Book of Abstracts, CEITEC PhD Retreat II, 20-21 April 2017, Telč, Czech Republic. 2017. ISBN 978-80-210-8551-0.

@proceedings{1382612,
   author = {Konhefr, Martin and Lacina, Karel and Skrutková Langmajerová, Monika and Glatz, Zdeněk and Skládal, Petr and Mazal, Ctibor},
   booktitle = {Book of Abstracts, CEITEC PhD Retreat II, 20-21 April 2017, Telč, Czech Republic},
   keywords = {iminoboronate, ferrocene, mass spectroscopy, cation, complex},
   language = {eng},
   isbn = {978-80-210-8551-0},
   title = {Unexpected structural distribution of electroactive ortho-Iminoboronate in protic and aprotic solvents determined using MS},
   url = {https://www.ceitec.eu/ceitec-phd-retreat-ii-book-of-abstracts/f34779#page=86},
   year = {2017}
}

TY  - CONF
ID  - 1382612
AU  - Konhefr, Martin - Lacina, Karel - Skrutková Langmajerová, Monika - Glatz, Zdeněk - Skládal, Petr - Mazal, Ctibor
PY  - 2017
TI  - Unexpected structural distribution of electroactive ortho-Iminoboronate in protic and aprotic solvents determined using MS
SN  - 9788021085510
KW  - iminoboronate, ferrocene, mass spectroscopy, cation, complex
UR  - https://www.ceitec.eu/ceitec-phd-retreat-ii-book-of-abstracts/f34779#page=86
N2  - As metal cations are essential not only in biology, their selective sensing is important also from an industrial and environmental viewpoint. These diverse applications have lead to the development of many molecular sensor systems for cationic guest species. A wide variety of e. g. macrocycles with ferrocene unit as redox signaling group have been synthesized [1]. Generally, complexation by these ligands (cations) affects the electrochemistry of the redox center, particularly when the guest molecule is either in close proximity to the iron atom or coordinated by functional groups that are conjugated with the ferrocene system. This configuration is observable in the aminoferrocene derivatives. As we studied the structure of novel iminoboronates bearing ferrocene as a signaling group for electrochemical sensing intended for a saccharide recognition [2], we realized that ortho-positioned iminoboronate in MS formed stable sodium and potassium chelates. These complexation properties were observed only in a protic solvent (methanol). None complexes were detected in an aprotic solvent (acetonitrile). Thus, methanol–hydroxyle rearrangement on boron atom in the proximity of imino group plays the most important role in the forming of an ideal surrounding (host) around complexed cation (guest) to form the chelate. In addition, this interacting site is close to redox-active center of ferrocene which reports on the binding event. Contrary to the protic solvent, stable ortho-iminoboronate anhydrides were observed in the aprotic solvent without any tendency to form chelates with cations.
ER  -

KONHEFR, Martin, Karel LACINA, Monika SKRUTKOVÁ LANGMAJEROVÁ, Zdeněk GLATZ, Petr SKLÁDAL a Ctibor MAZAL. Unexpected structural distribution of electroactive ortho-Iminoboronate in protic and aprotic solvents determined using MS. In \textit{Book of Abstracts, CEITEC PhD Retreat II, 20-21 April 2017, Telč, Czech Republic}. 2017. ISBN~978-80-210-8551-0.

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