Structural diversity in the products formed by the reactions of 2-arylselanyl pyridine derivatives and dihalogens

Riccardo Montis; Massimiliano Arca; M. Carla Aragoni; Alexander J. Blake; Carlo Castellano; Francesco Demartin; Francesco Isaia; Vito Lippolis; Anna Pintus; Eder J. Lenardão; Gelson Perin; Alice E. O'Connor; Samuel Thurow

doi:10.1039/C8NJ00495A

Structural diversity in the products formed by the reactions of 2-arylselanyl pyridine derivatives and dihalogens†

Riccardo Montis,

^a Massimiliano Arca,

^a M. Carla Aragoni,

*^a Alexander J. Blake,

^b Carlo Castellano,

^c Francesco Demartin,

^c Francesco Isaia,

^a Vito Lippolis,

*^a Anna Pintus,

^a Eder J. Lenardão,

^d Gelson Perin,

^d Alice E. O'Connor^b and Samuel Thurow

^d

Author affiliations

* Corresponding authors

^a Dipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, S.S. 554 Bivio per Sestu, 09042 Monserrato (CA), Italy
E-mail: lippolis@unica.it, aragoni@unica.it

^b School of Chemistry, University of Nottingham, Nottingham, UK

^c Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, 20133 Milano, Italy

^d Laboratório de Síntese Orgânica Limpa-LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, PO Box 354, 96010-900 Pelotas, RS, Brazil

Abstract

The reactivity of the 2-arylselanyl pyridine derivatives L1–L4 towards dihalogens X₂ (X = I, Br) and interhalogens IX (X = Cl, Br) was studied in CHCl₃ or CH₃CN. The solid products obtained were structurally characterized and their nature points out the preference for CT spoke adducts and for seesaw insertion adducts to be formed at the N-donor and Se-donor site, respectively. DFT calculations were performed to provide a rationale for the structural diversity observed in the products obtained.

This article is part of the themed collections: Selenium & Tellurium chemistry at the beginning of the 3rd millennium: a celebration of ICCST and The halogen bond: a new avenue in recognition and self-assembly

New Journal of Chemistry

Structural diversity in the products formed by the reactions of 2-arylselanyl pyridine derivatives and dihalogens†

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Structural diversity in the products formed by the reactions of 2-arylselanyl pyridine derivatives and dihalogens

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