Cargando…

Protonation of Borylated Carboxonium Derivative [2,6-B(10)H(8)O(2)CCH(3)](−): Theoretical and Experimental Investigation

The process of protonation of [2,6-B(10)H(8)O(2)CCH(3)](−) was investigated both theoretically and experimentally. The most suitable conditions for protonation of the derivative [2,6-B(10)H(8)O(2)CCH(3)](−) were found. The process of protonation was carried out in the presence of an excess of triflu...

Descripción completa

Detalles Bibliográficos
Autores principales: Klyukin, Ilya N., Kolbunova, Anastasia V., Novikov, Alexander S., Nelyubin, Aleksey V., Selivanov, Nikita A., Bykov, Alexander Yu., Klyukina, Alexandra A., Zhdanov, Andrey P., Zhizhin, Konstantin Yu., Kuznetsov, Nikolay T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9025682/
https://www.ncbi.nlm.nih.gov/pubmed/35457007
http://dx.doi.org/10.3390/ijms23084190
_version_ 1784690933451718656
author Klyukin, Ilya N.
Kolbunova, Anastasia V.
Novikov, Alexander S.
Nelyubin, Aleksey V.
Selivanov, Nikita A.
Bykov, Alexander Yu.
Klyukina, Alexandra A.
Zhdanov, Andrey P.
Zhizhin, Konstantin Yu.
Kuznetsov, Nikolay T.
author_facet Klyukin, Ilya N.
Kolbunova, Anastasia V.
Novikov, Alexander S.
Nelyubin, Aleksey V.
Selivanov, Nikita A.
Bykov, Alexander Yu.
Klyukina, Alexandra A.
Zhdanov, Andrey P.
Zhizhin, Konstantin Yu.
Kuznetsov, Nikolay T.
author_sort Klyukin, Ilya N.
collection PubMed
description The process of protonation of [2,6-B(10)H(8)O(2)CCH(3)](−) was investigated both theoretically and experimentally. The most suitable conditions for protonation of the derivative [2,6-B(10)H(8)O(2)CCH(3)](−) were found. The process of protonation was carried out in the presence of an excess of trifluoromethanesulfonic acid CF(3)SO(3)H at room temperature in dichloromethane solution. The structure of the resulting complex [2,6-B(10)H(8)O(2)CCH(3)*H(fac)](0) was established using NMR data and the results of DFT calculations. An additional proton atom H(fac) was found to be localized on one of the facets that was opposite the boron atom in a substituted position, and which bonded mainly with one apical boron atom. The main descriptors of the B-H(fac) bond were established theoretically using QTAIM and NBO approaches. In addition, the mechanism of [2,6-B(10)H(8)O(2)CCH(3)](−) protonation was investigated.
format Online
Article
Text
id pubmed-9025682
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-90256822022-04-23 Protonation of Borylated Carboxonium Derivative [2,6-B(10)H(8)O(2)CCH(3)](−): Theoretical and Experimental Investigation Klyukin, Ilya N. Kolbunova, Anastasia V. Novikov, Alexander S. Nelyubin, Aleksey V. Selivanov, Nikita A. Bykov, Alexander Yu. Klyukina, Alexandra A. Zhdanov, Andrey P. Zhizhin, Konstantin Yu. Kuznetsov, Nikolay T. Int J Mol Sci Article The process of protonation of [2,6-B(10)H(8)O(2)CCH(3)](−) was investigated both theoretically and experimentally. The most suitable conditions for protonation of the derivative [2,6-B(10)H(8)O(2)CCH(3)](−) were found. The process of protonation was carried out in the presence of an excess of trifluoromethanesulfonic acid CF(3)SO(3)H at room temperature in dichloromethane solution. The structure of the resulting complex [2,6-B(10)H(8)O(2)CCH(3)*H(fac)](0) was established using NMR data and the results of DFT calculations. An additional proton atom H(fac) was found to be localized on one of the facets that was opposite the boron atom in a substituted position, and which bonded mainly with one apical boron atom. The main descriptors of the B-H(fac) bond were established theoretically using QTAIM and NBO approaches. In addition, the mechanism of [2,6-B(10)H(8)O(2)CCH(3)](−) protonation was investigated. MDPI 2022-04-10 /pmc/articles/PMC9025682/ /pubmed/35457007 http://dx.doi.org/10.3390/ijms23084190 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Klyukin, Ilya N.
Kolbunova, Anastasia V.
Novikov, Alexander S.
Nelyubin, Aleksey V.
Selivanov, Nikita A.
Bykov, Alexander Yu.
Klyukina, Alexandra A.
Zhdanov, Andrey P.
Zhizhin, Konstantin Yu.
Kuznetsov, Nikolay T.
Protonation of Borylated Carboxonium Derivative [2,6-B(10)H(8)O(2)CCH(3)](−): Theoretical and Experimental Investigation
title Protonation of Borylated Carboxonium Derivative [2,6-B(10)H(8)O(2)CCH(3)](−): Theoretical and Experimental Investigation
title_full Protonation of Borylated Carboxonium Derivative [2,6-B(10)H(8)O(2)CCH(3)](−): Theoretical and Experimental Investigation
title_fullStr Protonation of Borylated Carboxonium Derivative [2,6-B(10)H(8)O(2)CCH(3)](−): Theoretical and Experimental Investigation
title_full_unstemmed Protonation of Borylated Carboxonium Derivative [2,6-B(10)H(8)O(2)CCH(3)](−): Theoretical and Experimental Investigation
title_short Protonation of Borylated Carboxonium Derivative [2,6-B(10)H(8)O(2)CCH(3)](−): Theoretical and Experimental Investigation
title_sort protonation of borylated carboxonium derivative [2,6-b(10)h(8)o(2)cch(3)](−): theoretical and experimental investigation
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9025682/
https://www.ncbi.nlm.nih.gov/pubmed/35457007
http://dx.doi.org/10.3390/ijms23084190
work_keys_str_mv AT klyukinilyan protonationofborylatedcarboxoniumderivative26b10h8o2cch3theoreticalandexperimentalinvestigation
AT kolbunovaanastasiav protonationofborylatedcarboxoniumderivative26b10h8o2cch3theoreticalandexperimentalinvestigation
AT novikovalexanders protonationofborylatedcarboxoniumderivative26b10h8o2cch3theoreticalandexperimentalinvestigation
AT nelyubinalekseyv protonationofborylatedcarboxoniumderivative26b10h8o2cch3theoreticalandexperimentalinvestigation
AT selivanovnikitaa protonationofborylatedcarboxoniumderivative26b10h8o2cch3theoreticalandexperimentalinvestigation
AT bykovalexanderyu protonationofborylatedcarboxoniumderivative26b10h8o2cch3theoreticalandexperimentalinvestigation
AT klyukinaalexandraa protonationofborylatedcarboxoniumderivative26b10h8o2cch3theoreticalandexperimentalinvestigation
AT zhdanovandreyp protonationofborylatedcarboxoniumderivative26b10h8o2cch3theoreticalandexperimentalinvestigation
AT zhizhinkonstantinyu protonationofborylatedcarboxoniumderivative26b10h8o2cch3theoreticalandexperimentalinvestigation
AT kuznetsovnikolayt protonationofborylatedcarboxoniumderivative26b10h8o2cch3theoreticalandexperimentalinvestigation