Vibrational and Electronic Circular Dichroism Study of Chiral Seleno Compounds Prepared from a Naphthol Based Diselenide

Year: 2022

Authors: Mangiavacchi F., Mazzeo G., Graziani MC., Marini F., Drabowicz J., Wielgus E., Sancineto L., Longhi G., Vivani R., Abbate S., Santi C.

Autors Affiliation: Univ Perugia, Dept Pharmaceut Sci, Grp Catalysis Synth & Organ Green Chem, Via Liceo 1, I-06123 Perugia, Italy; Univ Brescia, Dept Mol & Translat Med, Viale Europa 11, I-25123 Brescia, Italy; Polish Acad Sci, Ctr Mol & Macromol Studies, Sienkiewicza Lodz 112, PL-90363 Lodz, Poland; Jan Dlugosz Univ Czestochowa, Inst Chem, Armii Krajowej Ave 13-15, PL-42200 Czestochowa, Poland; CNR, Inst Nazl Ott INO, Res Unit Brescia, Via Branze 45, I-25123 Brescia, Italy; Univ Perugia, Dept Pharmaceut Sci, Grp Inorgan Chem, Via Liceo 1, I-06123 Perugia, Italy.

Abstract: Base induced activation of beta-naphthol toward the electrophilic aromatic substitution has been used for the synthesis of the unprecedented 1,1’-diselanediylbis(naphthalen-2-ol) fully characterized by means of NMR and X-Ray analysis. Its reactivity was studied and the synthesis of novel chiral selenium containing heterocycles was discovered. Chiroptical methods (VCD and ECD) were successfully used to define their absolute configuration and these results represent the first example reported for organoselenium derivatives.

Journal/Review: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Volume: 2022 (23)      Pages from: e202200282-1  to: e202200282-11

More Information: University of Perugia is acknowledged for the financial support under the frame of Fondo per la Ricerca di Base 2020. MUR (Ministero dell’Universita e della Ricerca, Rome, Italy) is acknowledged for the funding within the DELPHI project through the program Dipartimenti di Eccellenza 2018-2022. The research was conducted under the umbrella of the International Scientific Network SeSRedCat (Selenium Sulphur Redox and Catalysis). Funding from the Italian Ministry of Education, University and Research (MUR) through the PRIN 2017 program (Project 2017A4XRCA_003) is also gratefully acknowledged, as well as support for computational resources of Big&Open Data Innovation Laboratory (BODaI-Lab), University of Brescia, granted by Fondazione Cariplo and Regione Lombardia and of Computing Center CINECA (Bologna), Italy. The Authors are grateful to Letizia Monico (CNR-SCITEC, Perugia) for IR measurements. Open Access Funding provided by Universita degli Studi di Perugia within the CRUI-CARE Agreement.
KeyWords: Chirality; Circular Dichroism; Naphthol; Selenium; X-ray
DOI: 10.1002/ejoc.202200282

ImpactFactor: 2.800
Citations: 2
data from “WEB OF SCIENCE” (of Thomson Reuters) are update at: 2024-11-03
References taken from IsiWeb of Knowledge: (subscribers only)

Connecting to view paper tab on IsiWeb: Click here
Connecting to view citations from IsiWeb: Click here