Special Issue "Chalcogen-Nitrogen Chemistry"

Guest Editor
Prof. Dr. J. Derek Woollins
Department of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK
Website: http://www.eastchem.ac.uk/profiles/sta/woollins.html
E-Mail: j.d.woollins@st-andrews.ac.uk
Interests: synthesis; p block chemistry; phosphorus; sulphur; selenium; tellurium; structural science

Dear Colleagues,

Sulfur-nitrogen heterocycles (and Se-N/Te-N systems) have been known for many years but continue to excite attention as a consequence of the exciting new systems which are being prepared sometimes by rather unpredictable routes. Apart from fundamental synthetic and mechanistic chemistry new S-N, organo S-N (and their heavier selenium and tellurium congeners) have great potential in new electronic and magnetic materials. The area encompasses synthesis, heterocycles, ionic materials, conductors, superconductors, new magnetic materials and utilises a wide range of computational and spectroscopic methods.

Prof. Dr. Derek Woollins
Guest Editor

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• sulfur-nitrogen
• selenium-nitrogen
• thiazyl
• selenazole
• tellurazole
• heterocycle
• ring
• materials
• synthesis
• structure
• magnetism
• organo-sulfur-nitrogen
• organo-seleno-nitrogen

Type of Paper: Article
Title: Breathing Some New Life into an Old Topic: Chalcogen-Nitrogen Pi-heterocycles as Electron Acceptors
Authors: Anton V. Lonchakov ^1,2, Nina P. Gritsan ^1,2 and Andrey V. Zibarev ^2,3
Affiliations: ¹Institute of Chemical Kinetics and Combustion, Russian Academy of Sciences, 630090 Novosibirsk, Russia
²Department of Physics, National Research University - Novosibirsk State University, 630090 Novosibirsk, Russia
³Institute of Organic Chemistry, Russian Academy of Sciences, 630090 Novosibirsk, Russia
Abstract: Paper discusses design, synthesis and characterization of chalcogen-nitrogen pi-heterocycles possessing positive electron affinity together with their use for preparation of charge-transfer complexes and radical-anion salts - candidate building blocks of electrical and magnetic functional molecular materials.

Type of Paper: Article
Title: Synthesis, Structures and Electrochemistry of 1-triarylphosphinimino-1,3,5,2,4,6,8-trithiatetrazocines. Detection and decay of Trithiatetrazocinyl Radical Anions by SEEPR Spectroscopy
Authors: Xin Yu, Tracey L. Roemmele and René T. Boeré
Affiliations: Department of Chemistry and Biochemistry, University of Lethbridge, Lethbridge, Alberta, Canada T1K 3M4
Abstract: Reaction of the bicyclic sulfur-nitrogen heterocycles RC6H4CN5S3 (R = 4-CH3O, 4-CH3, 4-H, 4-Cl, 4-CF3, 3-CF3, with PR’3 (R’ =C6H5 or 4-CH3OC6H4) produces the corresponding 3-imino-7-aryl-1,3,5-trithia-2,4,6,8-trithiatetrazocines RC6H4CN4S3NPR’3. In all cases the endo-isomers were isolated and characterized by 1H, 31P, and 19F NMR, UV spectroscopy, and X-ray crystallography. Cyclic voltammetry (CV) studies of RC6H4CN4S3NPR’3 using a glassy carbon working electrode in CH2Cl2 with 0.4 M [nBu4N][PF6] all displayed two irreversible reduction processes at room temperature at approximately –1.9 V and –2.2 V, respectively, and one irreversible oxidation process at approximately 1.0 V (versus ferrocene/ferrocenium). The generated [RC6H4CN4S3NPR’3]–• radical anions (R’ = 4-CH3OC6H4, R = 4-CH3O, 4-H, 4-CF3,) were detected using the Simultaneous Electrochemical Electron Paramagnetic Resonance (SEEPR) method to give: (a) [4-CH3OC6H4CN4S3NP3]–•, estimated a(31P) = 0.660 mT, a(14N1) = 0.045 mT, a(14N2,3) = 0.256 mT, a(14N4,5) = 0.324 mT; (b) [C6H5CN4S3NP3]–•, estimated a(31P) = 0.613 mT, a(14N1) = 0.052 mT, a(14N2,3) = 0.255 mT, a(14N4,5) = 0.346 mT;(c) [3-CF3C6H4CN4S3NP3]–•, estimated a(31P) = 0.570 mT, a(14N1) = 0.031 mT, a(14N2,3) = 0.294 mT, a(14N4,5) = 0.325 mT. Bulk reductive electrolysis of a solution of [3-CF3C6H5CN4S3NP3] in CH2Cl2 produces a single radical with a(N) = 0.51 mT and g = 2.0105, consistent with production of the known radical [3-CF3-C6H4CN2S2]•.