Bismuthenium Cations for the Transport of Chloride Anions via Pnictogen Bonding DOI Creative Commons
Nathanael H. Hunter, François P. Gabbaı̈

Angewandte Chemie, Год журнала: 2024, Номер unknown

Опубликована: Авг. 24, 2024

Abstract Our interest in the design of heavy pnictogen‐based Lewis acids for anion trafficking across biological membrane mimics has led us to investigate trivalent bismuthenium cations as chloride transporters. Here, we describe two chlorodiarylbismuthines, elaborated on a peri ‐substituted naphthalene backbone and stabilized by an adjacent thio‐ or seleno‐ether functionality that engages bismuth center Ch→Bi interaction (Ch=chalcogen). These new derivatives are stable aqueous environment readiliy transport anions phospholipid‐based vesicles loaded with KCl. In addition establishing use such motifs transport, this investigation shows acidity, lipophilicity, thus properties depend nature chalcogen.

Язык: Английский

Recent advances in the stabilization of monomeric stibinidene chalcogenides and stibine chalcogenides DOI Creative Commons
John S. Wenger, Timothy C. Johnstone

Dalton Transactions, Год журнала: 2024, Номер 53(20), С. 8524 - 8534

Опубликована: Янв. 1, 2024

The synthetic strategies employed to isolate monomeric stibinidene chalcogenides (RSbCh) and stibine (R 3 SbCh) are discussed, a perspective on the outcomes future directions of this exciting area is provided.

Язык: Английский

Процитировано

3

Exploring the Effects of Se Basicity on a Te···Se Interaction Supported by a Rigid Indazolium Backbone DOI Creative Commons

Logan T. Maltz,

François P. Gabbaı̈

Organometallics, Год журнала: 2024, Номер 43(11), С. 1246 - 1255

Опубликована: Май 29, 2024

With an interest in chalcogen bonding, we use a rigid indazolium backbone to install formally zero-valent Se center next divalent Te center, allowing us investigate the effects of oxidation on observed Te···Se interaction. Through spectroscopic and computational comparison Se(0) species with its Se(II) counterpart their monochalcogen analogues, experimentally computationally effect modulating basicity resulting Comparison well-studied naphthalene acenaphthene variants indicates that increased allows for comparably strong interaction despite longer peri distances larger splay angle. Finally, our study illuminates potential non-innocence cationic organic substituents chalcogen-bonding catalysis transfer hydrogenation quinolines.

Язык: Английский

Процитировано

3

Affinity of Telluronium Chalcogen Bond Donors for Lewis Bases in Solution: A Critical Experimental‐Theoretical Joint Study DOI Creative Commons

Loïc Groslambert,

Yann Cornaton, Matej Ditte

и другие.

Chemistry - A European Journal, Год журнала: 2023, Номер 30(7)

Опубликована: Ноя. 16, 2023

Telluronium salts [Ar

Процитировано

6

Nickel-Catalyzed C(sp3)–Sb Coupling of Chlorostibines with Unactivated Alkyl Chlorides and In Vitro Anticancer Activity of Products DOI

Liyuan Le,

Mingming Yin,

Huifan Zeng

и другие.

Organic Letters, Год журнала: 2023, Номер 26(1), С. 344 - 349

Опубликована: Дек. 26, 2023

In this study, we present a nickel-catalyzed reductive C(sp3)–Sb coupling of unactivated alkyl chlorides with chlorostibines. This approach is highly versatile, tolerating various functional groups such as acetal, alkene, nitrile, amine, ester, silyl ether, thioether, and heterocyclic compounds. Notably, the late-stage modification bioactive molecules satisfactory anticancer activity against cancerous MDA-MB-231 also demonstrate potential application.

Язык: Английский

Процитировано

6

Nichtkovalente Organokatalyse mit Halogen‐, Chalkogen‐, Pniktogen‐ und Tetrelbrücken: neuere Entwicklungen DOI Creative Commons
Dragana Jovanovic,

Meghana Poliyodath Mohanan,

Stefan M. Huber

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(31)

Опубликована: Май 10, 2024

Abstract Die Anwendung nichtkovalenter Wechselwirkungen, welche auf elektrophilen Halogen‐, Chalkogen‐, Pniktogen‐ oder Tetrelzentren beruhen, hat in der Organokatalyse deutlich an Aufmerksamkeit gewonnen. Wir geben hier einen Überblick über die wichtigsten Entwicklungen letzten Jahre, mit einem Fokus experimentellen Studien und Katalysatoren, nicht‐transiente derartige Welchselwirkungen agieren.

Процитировано

2

Oxidation-dependent Lewis acidity in chalcogen adducts of Sb/P frustrated Lewis pairs DOI Creative Commons
Jonas Krieft, Beate Neumann,

Hans‐Georg Stammler

и другие.

Dalton Transactions, Год журнала: 2024, Номер 53(28), С. 11762 - 11768

Опубликована: Янв. 1, 2024

The reactions of the frustrated Lewis pair (F

Язык: Английский

Процитировано

2

A Sterically Accessible Monomeric Stibine Oxide Activates Organotetrel(IV) Halides, Including C–F and Si–F Bonds DOI Creative Commons
John S. Wenger, Timothy C. Johnstone

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(28), С. 19350 - 19359

Опубликована: Июль 3, 2024

Phosphine oxides and arsine are common laboratory reagents with diverse applications that stem from the chemistry exhibited by these monomeric species. Stibine are, in contrast, generally dimeric or oligomeric species because of reactivity-quenching self-association highly polarized stiboryl (Sb=O/Sb+–O–) group. We recently isolated Dipp3SbO (Dipp = 2,6-diisopropylphenyl), first example a kinetically stabilized stibine oxide, which exists as bench-stable solid bears an unperturbed Herein, we report isolation Mes3SbO (Mes mesityl), less bulky substituents maintain nature compound but unlock access to wider range reactivity at group relative Dipp3SbO. was found be potent Lewis base formation adducts main-group acids PbMe3Cl SnMe3Cl. The accessible acidity Sb atom results change GeMe3Cl, SiMe3Cl, CPh3Cl. With species, formally adds E–Cl (E Ge, Si, C) bond across unsaturated form 5-coordinate stiborane. biphilicity is sufficiently activate even C–F Si–F bonds C(p-MeOPh)3F SiEt3F, respectively. These mark significant contribution increasingly rich literature on polar, motifs. Furthermore, highlight utility kinetic stabilization approach unusual bonding motifs unquenched can leveraged for small-molecule activation.

Язык: Английский

Процитировано

2

Pnictogen Bonding at the Core of a Carbene-Stiborane-Gold Complex: Impact on Structure and Reactivity DOI Creative Commons

Paula Castro Castro,

François P. Gabbaı̈

Organometallics, Год журнала: 2024, Номер 43(19), С. 2334 - 2341

Опубликована: Сен. 26, 2024

Our interest in the design of ambiphilic ligands and their coordination to gold has led us synthesize an indazol-3-ylidene chloride complex functionalized at 4-position indazole backbone by a stibine functionality. The antimony center this new cleanly reacts with

Язык: Английский

Процитировано

2

Pnictogen‐Bonding Enzymes DOI Creative Commons
Giacomo Renno, Dongping Chen, Qingxia Zhang

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(45)

Опубликована: Июль 5, 2024

Abstract The objective of this study was to create artificial enzymes that capitalize on pnictogen bonding, a σ‐hole interaction is essentially absent in biocatalysis. For purpose, stibine catalysts were equipped with biotin derivative and combined streptavidin mutants identify an efficient transfer hydrogenation catalyst for the reduction fluorogenic quinoline substrate. Increased catalytic activity from wild‐type best coincides depth σ hole Sb(V) center, emergence saturation kinetic behavior. Michaelis–Menten analysis reveals transition‐state recognition low micromolar range, more than three orders magnitude stronger millimolar substrate recognition. Carboxylates preferred by contribute hydrogen‐bonded ion pairing anion‐π interactions emerging pyridinium product. challenging stereoselectivity aqueous systems further emphasizes compatibility bonding higher order catalysis.

Язык: Английский

Процитировано

1

Bismuthenium Cations for the Transport of Chloride Anions via Pnictogen Bonding DOI Creative Commons
Nathanael H. Hunter, François P. Gabbaı̈

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Авг. 24, 2024

Our interest in the design of heavy pnictogen-based Lewis acids for anion trafficking across biological membrane mimics has led us to investigate trivalent bismuthenium cations as chloride transporters. Here, we describe two chlorodiarylbismuthines, elaborated on a peri-substituted naphthalene backbone and stabilized by an adjacent thio- or seleno-ether functionality that engages bismuth center Ch→Bi interaction (Ch=chalcogen). These new derivatives are stable aqueous environment readiliy transport anions phospholipid-based vesicles loaded with KCl. In addition establishing use such motifs transport, this investigation shows acidity, lipophilicity, thus properties depend nature chalcogen.

Язык: Английский

Процитировано

1