Most of traditional and contemporary interest in s-tetrazine derivatives focuses onto their redox properties, reactivity and energy density. In recent times, however, an increasing number of reports highlighted the possible usefulness of the s-tetrazine moiety as a binding site for anionic and electron rich species, according to the high and positive quadrupolar moment of this heterocycle and the consequent strength of anion-p and lone pair-p interactions. Herein, after giving a quick perspective on s-tetrazine properties and on how they foster these types of p interactions, we present statistical and critical examination of the available structural data, doing justice to the debated topic of the existence and directionality of anion and lone pair-p interactions. Finally, available literature material concerning the usage of s-tetrazine as supramolecular binding site in solution, i.e. paving the way to applications such as molecular recognition and sensing, is presented and discussed.

Anion-π and lone pair-π interactions with s-tetrazine-based ligands / Matteo Savastano , Celeste García-Gallarín, María Dolores López de la Torre, Carla Bazzicalupi, Antonio Bianchi, Manuel Melguizo. - In: COORDINATION CHEMISTRY REVIEWS. - ISSN 0010-8545. - STAMPA. - 397:(2019), pp. 112-137. [10.1016/j.ccr.2019.06.016]

Anion-π and lone pair-π interactions with s-tetrazine-based ligands

Matteo Savastano;Carla Bazzicalupi;Antonio Bianchi
;
2019

Abstract

Most of traditional and contemporary interest in s-tetrazine derivatives focuses onto their redox properties, reactivity and energy density. In recent times, however, an increasing number of reports highlighted the possible usefulness of the s-tetrazine moiety as a binding site for anionic and electron rich species, according to the high and positive quadrupolar moment of this heterocycle and the consequent strength of anion-p and lone pair-p interactions. Herein, after giving a quick perspective on s-tetrazine properties and on how they foster these types of p interactions, we present statistical and critical examination of the available structural data, doing justice to the debated topic of the existence and directionality of anion and lone pair-p interactions. Finally, available literature material concerning the usage of s-tetrazine as supramolecular binding site in solution, i.e. paving the way to applications such as molecular recognition and sensing, is presented and discussed.
2019
397
112
137
Matteo Savastano , Celeste García-Gallarín, María Dolores López de la Torre, Carla Bazzicalupi, Antonio Bianchi, Manuel Melguizo...espandi
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1194679
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