The reactivity of 1,1 '-bis(3-methyl-4-imidazolin-2-selone)methane (L1) and 1,2-bis(3-methyl-4-imidazolin-2-selone)ethane (L2) toward I2 has been explored in MeCN under different experimental conditions and compared with that in CH2Cl2. The compounds [L1 '](I)2 (I), [L1I]n(I)n (II), [L1(mu-Se)](I)2 center dot 1/2H2O (III), [L1I](I3)center dot 2I2 (IV), and [L2](I)2 center dot MeCN (V) were obtained and characterized. X-ray diffraction analyses point out an ionic nature for these compounds, which is presumably favored by the polarity of the solvent used. In particular, [L1I]n(I)n (II) represents the first example of an iodonium complex of imidazoline-2-selone derivatives, while [L1(mu-Se)](I)2 center dot 1/2H2O (III) represents a unique example of a dicationic [RSeSeSeR] triselane. Density functional theory calculations have allowed us to better understand the nature of the obtained compounds and to justify their formations in polarizing reaction conditions rather than in low polar solvents.

Role of the Solvent in the Reactivity of Bis-4-imidazoline-2-selone Derivatives toward I2: An Experimental and Theoretical Approach / M.C. Aragoni, M. Arca, C. Caltagirone, C. Castellano, F. Demartin, P.G. Jones, T. Pivetta, E. Podda, V. Lippolis, S. Murgia, G. Picci. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 87:22(2022 Nov 18), pp. 15448-15465. [10.1021/acs.joc.2c01982]

Role of the Solvent in the Reactivity of Bis-4-imidazoline-2-selone Derivatives toward I2: An Experimental and Theoretical Approach

C. Castellano;F. Demartin;
2022

Abstract

The reactivity of 1,1 '-bis(3-methyl-4-imidazolin-2-selone)methane (L1) and 1,2-bis(3-methyl-4-imidazolin-2-selone)ethane (L2) toward I2 has been explored in MeCN under different experimental conditions and compared with that in CH2Cl2. The compounds [L1 '](I)2 (I), [L1I]n(I)n (II), [L1(mu-Se)](I)2 center dot 1/2H2O (III), [L1I](I3)center dot 2I2 (IV), and [L2](I)2 center dot MeCN (V) were obtained and characterized. X-ray diffraction analyses point out an ionic nature for these compounds, which is presumably favored by the polarity of the solvent used. In particular, [L1I]n(I)n (II) represents the first example of an iodonium complex of imidazoline-2-selone derivatives, while [L1(mu-Se)](I)2 center dot 1/2H2O (III) represents a unique example of a dicationic [RSeSeSeR] triselane. Density functional theory calculations have allowed us to better understand the nature of the obtained compounds and to justify their formations in polarizing reaction conditions rather than in low polar solvents.
Settore CHIM/03 - Chimica Generale e Inorganica
18-nov-2022
1-nov-2022
Article (author)
File in questo prodotto:
File Dimensione Formato  
acs.joc.2c01982_Lippolis_published.pdf

accesso riservato

Descrizione: articolo
Tipologia: Publisher's version/PDF
Dimensione 5.66 MB
Formato Adobe PDF
5.66 MB Adobe PDF   Visualizza/Apri   Richiedi una copia
JOC_AAM.pdf

Open Access dal 02/11/2023

Tipologia: Post-print, accepted manuscript ecc. (versione accettata dall'editore)
Dimensione 1.92 MB
Formato Adobe PDF
1.92 MB Adobe PDF Visualizza/Apri
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/947336
Citazioni
  • ???jsp.display-item.citation.pmc??? 0
  • Scopus 3
  • ???jsp.display-item.citation.isi??? 2
social impact