Cargando…

Differential Binding of Tetrel-Bonding Bipodal Receptors to Monatomic and Polyatomic Anions

Previous work has demonstrated that a bidentate receptor containing a pair of Sn atoms can engage in very strong interactions with halide ions via tetrel bonds. The question that is addressed here concerns the possibility that a receptor of this type might be designed that would preferentially bind...

Descripción completa

Detalles Bibliográficos
Autor principal: Scheiner, Steve
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6358819/
https://www.ncbi.nlm.nih.gov/pubmed/30634503
http://dx.doi.org/10.3390/molecules24020227
_version_ 1783392076438700032
author Scheiner, Steve
author_facet Scheiner, Steve
author_sort Scheiner, Steve
collection PubMed
description Previous work has demonstrated that a bidentate receptor containing a pair of Sn atoms can engage in very strong interactions with halide ions via tetrel bonds. The question that is addressed here concerns the possibility that a receptor of this type might be designed that would preferentially bind a polyatomic over a monatomic anion since the former might better span the distance between the two Sn atoms. The binding of Cl(−) was thus compared to that of HCOO(−), HSO(4)(−), and H(2)PO(4)(−) with a wide variety of bidentate receptors. A pair of SnFH(2) groups, as strong tetrel-binding agents, were first added to a phenyl ring in ortho, meta, and para arrangements. These same groups were also added in 1,3 and 1,4 positions of an aliphatic cyclohexyl ring. The tetrel-bonding groups were placed at the termini of (-C≡C-)(n) (n = 1,2) extending arms so as to further separate the two Sn atoms. Finally, the Sn atoms were incorporated directly into an eight-membered ring, rather than as appendages. The ordering of the binding energetics follows the HCO(2)(−) > Cl(−) > H(2)PO(4)(−) > HSO(4)(−) general pattern, with some variations in selected systems. The tetrel bonding is strong enough that in most cases, it engenders internal deformations within the receptors that allow them to engage in bidentate bonding, even for the monatomic chloride, which mutes any effects of a long Sn···Sn distance within the receptor.
format Online
Article
Text
id pubmed-6358819
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-63588192019-02-06 Differential Binding of Tetrel-Bonding Bipodal Receptors to Monatomic and Polyatomic Anions Scheiner, Steve Molecules Article Previous work has demonstrated that a bidentate receptor containing a pair of Sn atoms can engage in very strong interactions with halide ions via tetrel bonds. The question that is addressed here concerns the possibility that a receptor of this type might be designed that would preferentially bind a polyatomic over a monatomic anion since the former might better span the distance between the two Sn atoms. The binding of Cl(−) was thus compared to that of HCOO(−), HSO(4)(−), and H(2)PO(4)(−) with a wide variety of bidentate receptors. A pair of SnFH(2) groups, as strong tetrel-binding agents, were first added to a phenyl ring in ortho, meta, and para arrangements. These same groups were also added in 1,3 and 1,4 positions of an aliphatic cyclohexyl ring. The tetrel-bonding groups were placed at the termini of (-C≡C-)(n) (n = 1,2) extending arms so as to further separate the two Sn atoms. Finally, the Sn atoms were incorporated directly into an eight-membered ring, rather than as appendages. The ordering of the binding energetics follows the HCO(2)(−) > Cl(−) > H(2)PO(4)(−) > HSO(4)(−) general pattern, with some variations in selected systems. The tetrel bonding is strong enough that in most cases, it engenders internal deformations within the receptors that allow them to engage in bidentate bonding, even for the monatomic chloride, which mutes any effects of a long Sn···Sn distance within the receptor. MDPI 2019-01-09 /pmc/articles/PMC6358819/ /pubmed/30634503 http://dx.doi.org/10.3390/molecules24020227 Text en © 2019 by the author. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Scheiner, Steve
Differential Binding of Tetrel-Bonding Bipodal Receptors to Monatomic and Polyatomic Anions
title Differential Binding of Tetrel-Bonding Bipodal Receptors to Monatomic and Polyatomic Anions
title_full Differential Binding of Tetrel-Bonding Bipodal Receptors to Monatomic and Polyatomic Anions
title_fullStr Differential Binding of Tetrel-Bonding Bipodal Receptors to Monatomic and Polyatomic Anions
title_full_unstemmed Differential Binding of Tetrel-Bonding Bipodal Receptors to Monatomic and Polyatomic Anions
title_short Differential Binding of Tetrel-Bonding Bipodal Receptors to Monatomic and Polyatomic Anions
title_sort differential binding of tetrel-bonding bipodal receptors to monatomic and polyatomic anions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6358819/
https://www.ncbi.nlm.nih.gov/pubmed/30634503
http://dx.doi.org/10.3390/molecules24020227
work_keys_str_mv AT scheinersteve differentialbindingoftetrelbondingbipodalreceptorstomonatomicandpolyatomicanions