288-05-1Relevant articles and documents
Conformational analysis of 2-formylselenophene by means of 13C1H, 13C13C, and 77Se1H spinspin coupling constants
Rusakov, Yury Yu.,Krivdin, Leonid B.,Istomina, Natalia V.,Levanova, Ekaterina P.,Levkovskaya, Galina G.
, p. 734 - 738 (2009)
Theoretical energy-based conformational analysis of 2-formylselenophene performed at the MP2/6311G*level together with experimental measurements and SOPPA/aug-cc-pVTZ-J calculations of its 13C1H, 13C13C, and 77Se1H spinspin coupling constants showed that this compound predominantly adopts the s-cis conformation. Most of the spinspin coupling constants under study, especially vicinal 77Se1H couplings, demonstrate remarkable stereochemical behaviour with respect to the internal rotation of the formyl group, which is of major importance in stereochemical studies of the related selenium-containing compounds. CSIRO 2009.
Improved Synthesis of Selenophene
Mohmand, Shamsher,Bargon, Joachim,Waltman, Robert J.
, p. 3544 - 3545 (1983)
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The NMR Spectrum and Total Geometry of Selenophene Determined in the Liquid Crystal Medium ZLI 1167
Bechtold, William,Magruder, Brock G.,Goldstein, J. H.
, p. 173 - 175 (1982)
The calculated 12C, 13C and 77Se spectra of selenophene have been reproduced from the observed proton NMR spectrum in the orienting medium Merck ZLI 1167, and the entire ring structure computed.The effects on structure of vibration, solvent dependence of couplings and temperature have been explored.Most notable was the observation of a substantial increase in the Se-C bond length, comparable to that previously reported for selenophenone in Merck Phase IV.
Structural trends of 77Se-1H spin-spin coupling constants and conformational behavior of 2-substituted selenophenes
Rusakov, Yury Yu.,Krivdin, Leonid B.,Sauer, Stephan P. A.,Levanova, Ekaterina P.,Levkovskaya, Galina G.
experimental part, p. 44 - 52 (2010/04/06)
Experimental measurements and second-order polarization propagator approach (SOPPA) calculations of 77Se-1H spin-spin coupling constants together with theoretical energy-based conformational analysis in the series of 2-substituted selenophenes have been carried out. A new basis set optimized for the calculation of 77Se-1H spin-spin coupling constants has been introduced by extending the aug-cc-pVTZ-J basis for selenium. Most of the spin-spin coupling constants under study, especially vicinal 77Se-1H couplings, demonstrated a remarkable stereochemical behavior with respect to the internal rotation of the substituent in the 2-position of the selenophene ring, which is of major importance in the stereochemical studies of therelated organoselenium compounds. Copyright
Synthesis, properties, oxidation, and electrochemistry of 1,2- dichalcogenins
Block, Eric,Birringer, Marc,Deorazio, Russell,Fabian, Juergen,Glass, Richard S.,Guo, Chuangxing,He, Chunhong,Lorance, Edward,Qian, Quangsheng,Schroeder, T. Benjamin,Shan, Zhixing,Thiruvazhi, Mohan,Wilson, George S.,Zhang, Xing
, p. 5052 - 5064 (2007/10/03)
Syntheses are presented of the 1,2-dichalcogenins: 1,2-dithiin, 1,2- diselenin, and 2-selenathiin, both substituted and unsubstituted. 1,2-Dithiin and 1,2-diselenin are prepared by reaction of PhCH2XNa (X = S or Se) with 1,4-bis(trimethylsilyl)-1,3-butadiyne followed by reductive cleavage and oxidation. 2-Selenathiin is similarly prepared using a mixture of PhCH2SeNa and PhCH2SNa. Reaction of titanacyclopentadienes with (SCN)2 or (SeCN)2 followed by bis(thiocyanate) or bis(selenocyanate) cyclization affords substituted 1,2-dithiins or 1,2-diselenins, respectively. With S2Cl2, 1,2- dithiins are directly formed from titanacyclopentadienes. Oxidation of 1,2- dithiins and 1,2-diselenins gives the corresponding 1-oxide and, with 1,2- dithiins and excess oxidant, 1,1-dioxides; oxidation of 2-selenathiin gives the 2-oxide. Electrochemical oxidation of 1,2-dichalcogenins, which have a twisted geometry, affords planar radical cations by an EC mechanism. One- electron AlCl3 oxidation of 3,6-diphenyl-1,2-dithiin gives the corresponding radical cation, characterized by EPR spectroscopy. Theoretical calculations result in a flattened structure for the 1,2-dithiin radical cation and a fully planar structure for the 1,2-diselenin radical cation. The 77Se NMR chemical shifts of 1,2-diselenin are characteristically high-field-shifted with respect to open chain diselenides in good agreement with results of GIAO-DFT calculations based on MP2 and DFT optimum geometries.
