Thiazolium Salts as Chalcogen Bond Donors

被引：20

作者：

Konidaris, Kostantis ^{[1
]}

Daolio, Andrea ^{[1
]}

Pizzi, Andrea ^{[1
]}

Scilabra, Patrick ^{[1
]}

Terraneo, Giancarlo ^{[1
]}

Quici, Silvio ^{[2
]}

Murray, Jane S. ^{[3
]}

Politzer, Peter ^{[3
]}

Resnati, Giuseppe ^{[1
]}

机构：

[1] Politecn Milan, NFMLab, Dept Chem Mat & Chem Engn Giulio Natta, I-20133 Milan, Italy

[2] Consiglio Nazl Ric CNR, Ist Sci & Tecnol Chim Giulio Natta SCITEC, I-20133 Milan, Italy

[3] Univ New Orleans, Dept Chem, New Orleans, LA 70148 USA

来源：

CRYSTAL GROWTH & DESIGN | 2022年 / 22卷 / 08期

关键词：

BINDING; CELLS; HOLE; DYE; DERIVATIVES; DISCOVERY; MECHANISM; INSIGHTS; RECEPTOR; EBSELEN;

D O I：

10.1021/acs.cgd.2c00510

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The nitrogen atom is commonly considered to be the positive site in thiazolium cations. Counterintuitively, the shortest cation center dot center dot center dot anion contacts in thiazolium salts and their benzoderivatives involve the sulfur atom. The geometric features of these contacts allow for their rationalization as charge assisted chalcogen bonds (ChBs). Analyses of the Cambridge Structural Database and calculation of the surface electrostatic potential of benzo[d]thiazolium cations support this rationalization. The relevance and impact of the general tendency of thiazolium derivatives to function as ChB donors are exemplified by the ChBs as short as 87% of the sum of van der Waals radii of involved atoms in thiamine monophosphate, a key compound in human metabolism, and in two commonly used thiazolium organo-catalysts.

引用

页码：4987 / 4995

页数：9

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