Skip to main content
Log in

Structural and Reactivity Aspects of Organoselenium and Tellurium Cations

  • Research Article
  • Published:
Proceedings of the National Academy of Sciences, India Section A: Physical Sciences Aims and scope Submit manuscript

Abstract

In this brief review, synthesis, structural and reactivity aspects of heavier organochalcogen (RS+n, RSe+n, RTe+n;n = 1–3) cations have been described. The orgaosulfenium ions (RS+) and related sulfur cations have been already reported in detail and, therefore, will not be discussed here. Structurally characterised organochalcogen cations of heavier chalcogens (Se, Te) will be the main focus of the review and only a few relevant examples, which are not structurally characterized, will be discussed for comparison purposes. The collection of chalcogen cations enlisted here shall benefit the readers who are interested in isolating and utilizing the organochalcogen cations for particular applications.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Scheme 1
Scheme 2
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 3
Fig. 6
Fig. 7
Scheme 4
Scheme 5
Fig. 8
Scheme 6
Scheme 7
Scheme 8
Fig. 9
Scheme 9
Fig. 10
Scheme 10
Fig. 11
Scheme 11
Scheme 12
Fig. 12
Scheme 13
Scheme 14
Scheme 15
Scheme 16

Similar content being viewed by others

References

  1. Bhuyan BJ, Mugesh G (2011) Biological and biochemical aspects of selenium compounds. In: Wirth T (ed) Organoselenium shemistry: synthesis and reactions. Wiley, Germany, pp 361–396. doi:10.1002/9783527641949.ch9

  2. Singh FV, Wirth T (2011) Selenium compounds as ligands and catalysts. In: Wirth T (ed) Organoselenium chemistry. Wiley, Germany, pp 321–360. doi:10.1002/9783527641949.ch8

  3. Santi C, Lorenzo RD, Tidei C, Bagnoli L, Wirth T (2012) Stereoselective selenium catalyzed dihydroxylation and hydroxymethoxylation of alkenes. Tetrahedron 68:10530–10535

    Article  Google Scholar 

  4. Manjare ST, Kim Y, Churchill DG (2014) Selenium- and tellurium-containing fluorescent molecular probes for the detection of biologically important analysts. Acc Chem Res 47:2985–2998

    Article  Google Scholar 

  5. Kremer A, Aurisicchio C, Leo FD, Ventura B, Wouters J, Armaroli N, Barbieri A, Bonifazi D (2015) Walking down the chalcogenic group of the periodic table: from singlet to triplet organic emitters. Chem Eur J 21:15377–15387

    Article  Google Scholar 

  6. Zhao L, Li J, Li Y, Liu J, Wirth T, Li Z (2012) Selenium-containing naphthalimides as anticancer agents: design, synthesis and bioactivity. Bioorg Med Chem 20:2558–2563

    Article  Google Scholar 

  7. Singh FV, Wirth T Edited by Patai S, Rappoport Z (2012) Stereoselective reactions of organoselenium reagents including catalysis. Chem Org Selenium Tellurium Compd 3(Pt. 1):303–355. Wiley 1986–1987, Chichester, UK. CODEN:56LRA9

  8. Browne DM, Niyomura O, Wirth T (2007) Catalytic use of selenium electrophiles in cyclization. Org Lett 9:3169–3171

    Article  Google Scholar 

  9. Prasad ChD, Balkrishna SJ, Kumar A, Bhakuni BS, Shrimali K, Biswas S, Kumar S (2013) Transition-metal-free synthesis of unsymmetrical diaryl chalcogenides from arenes and diaryl dichalcogenides. J Org Chem 78:1434–1443

    Article  Google Scholar 

  10. Denmark SE, Chi HM (2014) Lewis base catalyzed, enantioselective, intramolecular sulfenoamination of olefins. J Am Chem Soc 136:8915–8918

    Article  Google Scholar 

  11. Denmark SE, Kuester WE, Burk MT (2012) Catalytic, asymmetric halofunctionalization of alkenes-a critical perspective. Angew Chem Int Ed 51:10938–10953

    Article  Google Scholar 

  12. Fujihara H, Mima H, Furukawa N (1995) First isolation and crystal structure of heavier chalcogenenium cations (RSe+, RTe+) stabilized by two neighbouring amino groups. J Am Chem Soc 117:10153–10154

    Article  Google Scholar 

  13. Poleschner H, Seppelt K (2004) First detection of a selenenyl fluoride ArSe-F by NMR spectroscopy: the nature of Ar2Se2/XeF2 and ArSe-SiMe3/XeF2 reagents. Chem Eur J 10:6565–6574

    Article  Google Scholar 

  14. Pop A, Silvestru A, Juárez-Pérez EJ, Arca M, Lippolis V, Silvestru C (2014) Organoselenium(II) halides containing the pincer 2,6-(Me2NCH2)2C6H3 ligand-an experimental and theoretical investigation. Dalton Trans 43:2221–2223

    Article  Google Scholar 

  15. Wirth T (2000) Organoselenium chemistry in stereoselective reactions. Angew Chem Int Ed 39:3740–3749

    Article  Google Scholar 

  16. Browne DM, Wirth T (2006) New developments with chiral electrophilic selenium reagents. Curr Org Chem 10:1893–1903

    Article  Google Scholar 

  17. Freudendanl DM, Shahzad SA, Wirth T (2009) Recent advances in organoselenium chemistry. Eur J Org Chem 2009(11):1649–1664

  18. Beleaga A, Bojan VA, Pöllnitz A, Rat CI, Silvestru C (2011) Organomercury(II) and tellurium(II) compounds with the “pincer” ligand 2,6-[O(CH2CH2)2NCH2]2C6H3-stabilization of an unusual organotellurium(II) cationic species. Dalton Trans 40:8830

    Article  Google Scholar 

  19. Jeske J, du Mont W-W, Ruthe F, Jones PG, Mercuri LM, Deplano P (2000) Novel mesityltellurium cations from selenenation and tellurenation reactions of dimesityl telluride in the presence of the Br2/AgSbF6 reagent. Eur J Inorg Chem 2000(7):1591–1599

  20. Jeske J, du Mont W-W, Jones PG (1997) Synthesis of a triiodide-Like pentamesityltritelluriurn cation by Addition of dirnesityltelluride to the remarkably electrophilic trimesitylditelluronium ion. Angew Chem Int Ed 36:2219–2221

    Article  Google Scholar 

  21. Varga RA, Kulcsar M, Silvestru A (2010) [2,6-Bis(dimethyl-amino-meth-yl)phen-yl]selenium bromide monohydrate. Acta Crystallogr Sect E Struct Rep Online E66:o771

    Article  Google Scholar 

  22. Slattery JM, Fish C, Green M, Hooper TN, Jeffery JC, Kilby RJ, Lynam JM, McGrady JE, Pantazis DA, Russell CA, Willans CE (2007) Evidence for a SN2-type pathway for phosphine exchange in phosphine-phosphenium cations, [R2P-PR’3]+. Chem Eur J13:6967–6974

    Article  Google Scholar 

  23. Sugamata K, Sasamori T, Tokitoh N (2012) Generation of an organotellurium(II) cation. Eur J Inorg Chem 5:775–778

    Article  Google Scholar 

  24. Köllemann C, Sladky F (1990) Phospanstabilisierte organyltellurenylkationen, [RTe(PR’3)]+. J Organomet Chem 396:C1–C3

    Article  Google Scholar 

  25. Beckmann J, Bolsinger J, Duthie A, Finke P, Lork E, Ludtke C, Mallow O, Mebs S (2012) Mesityltellurenyl cations stabilized by triphenylpnictogens [MesTe(EPh3)]+ (E = P, As, Sb). Inorg Chem 51:12395–12406

    Article  Google Scholar 

  26. Beckmann J, Finke P, Heitz S, Hesse M (2008) Aryltellurenyl cation [RTe(CR′2)]+ stabilized by an N-Heterocyclic carbene. Eur J Inorg Chem 11:1921–1925

    Article  Google Scholar 

  27. Yadav S, Raju S, Singh HB, Butcher RJ (2016) Selone-stabilized aryltellurenyl cations. Dalton Trans 45:8458–8467

    Article  Google Scholar 

  28. Singh VP, Singh HB, Butcher RJ (2010) Stable selenenium cations: unusual reactivity and excellent glutathione peroxidase-like activity. Eur J Inorg Chem 4:637–647

    Article  Google Scholar 

  29. Rakesh P, Singh HB, Butcher RJ (2013) Synthesis of selenenium ions: isolation of highly conjugated, pH-sensitive 4,4′-bis(methylimino)-1,1′-binaphthylene-5-diselenenium(II) triflate. Organometallics 32:7275–7282

    Article  Google Scholar 

  30. Dutton JL, Tuononen HM, Ragogna PJ (2009) Tellurium(II)-centered dications from the pseudohalide Te(OTf)2. Angew Chem Int Ed 48:4409–4413

    Article  Google Scholar 

  31. Dutton JL, Tabeshi R, Jennings MC, Lough AJ, Ragogna PJ (2007) Redox reactions between phosphines (R3P; R = nBu, Ph) or carbene (iPr2IM) and Chalcogen tetrahalides ChX4 (iPr2IM = 2,5-diisopropylimidazole-2-ylidene; Ch = Se, Te; X = Cl, Br). Inorg Chem 46:8594–8602

    Article  Google Scholar 

  32. Dutton JL, Sutrisno A, Schurkob RW, Ragogna PJ (2008) Synthesis and characterization of cationic selenium–nitrogen heterocycles from tert-butyl-DAB (DAB = 1,4-di-tert-butyl-1,3-diazabutadiene) and SeX4 via the reductive elimination of X2 (X = Cl, Br): a distinct contrast with tellurium. Dalton Trans 3470–3477. doi:10.1039/b719779a

  33. Gushwa AF, Richards AF (2008) Selenium heterocycles: reactions of SeX4 (X = Cl, Br) with the enamine form of β-diketiminato ligands. Eur J Inorg Chem 728–736

  34. Kuhn N, Abu-Rayyan A, Piludu C, Steimann M (2005) Reaction of tellurium tetraiodide with 2,3-dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene. Heteroat Chem 16:316–319

    Article  Google Scholar 

  35. Martin CD, Jennings MC, Ferguson MJ, Ragogna PJ (2009) Dicationic sulfur analogues of N-heterocyclic silylenes and phosphenium cations. Angew Chem Int Ed 121:2244–2247

    Article  Google Scholar 

  36. Dutton JL, Tuononen HM, Jennings MC, Ragogna PJ (2006) Extending the series: synthesis and characterization of a dicationic N-heterocyclic selenium carbene analogue. J Am Chem Soc 128:12624–12625

    Article  Google Scholar 

  37. Bergholdt AB, Kobayashi K, Horn E, Takahashi O, Sato S, Furukawa N, Yokoyama M, Yamaguchi K (1998) Crystal structures and ab Initio calculations of new dicationic telluranes (λ 4-Tellane), [10-Te-4(C2X2)]2+ (X) S, Se): positively charged hypervalent bonding systems. J Am Chem Soc 120:1230–1236

    Article  Google Scholar 

  38. Fujihara H, Mima H, Erata T, Furukawa N (1992) Hypervalent selenurane with the chalcogenium cation (Se+, S+) from 1,11-(methanoselenomethano)-5H,7H-dibenzo[b, g [1, 5]diselenocin and Its sulfur derivative: interconvertible redox structures by multicenter chalcogenide participation. J Am Chem Soc 114:3118–3120

    Article  Google Scholar 

  39. Martin CD, Ragogna PJ (2010) Synthesis and reactivity of sulfur(II) dications stabilized using monodentate ligands. Inorg Chem 49:8164–8172

    Article  Google Scholar 

  40. Martin CD, Jennings MC, Ferguson MJ, Ragogna PJ (2009) Dicationic sulfur analogues of N-heterocyclic silylenes and phosphenium cations. Angew Chem Int Ed 48:2210–2213

    Article  Google Scholar 

  41. Martin CD, Ragogna PJ (2010) Reactions of r-diimine ligands with the in Situ generated “S(OTf)2” synthon. Inorg Chem 49:4324–4330

    Article  Google Scholar 

  42. Dutton JL, Ragogna PJ (2010) Dicationic tellurium analogues of the classic N-heterocyclic carbene. Chem Eur J 16:12454–12461

    Article  Google Scholar 

  43. Dutton JL, Ragogna PJ (2009) Donor-acceptor chemistry at heavy chalcogen centers. Inorg Chem 48:1722–1730

    Article  Google Scholar 

  44. Martin CD, Le CM, Ragogna PJ (2009) Remarkably stable chalcogen(II) dications. J Am Chem Soc 131:15126–15127

    Article  Google Scholar 

  45. Kozma A, Petuškova J, Lehmann CM, Alcarazo M (2013) Synthesis, structure and reactivity of cyclopropenyl-1-ylidene stabilized S(II), Se(II) and Te(II) mono- and dications. Chem Commun 49:4145–4147

    Article  Google Scholar 

  46. Evans DH, Gruhn NE, Jin J, Li B, Lorance E, Okumura N, Macías-Ruvalcaba NA, Zakai UI, Zhang S-Z, Block E, Glass RS (2010) Electrochemical and chemical oxidation of dithia-, diselena-, ditellura-, selenathia-, and tellurathiamesocycles and stability of the oxidized species. J Org Chem 75:1997–2009

    Article  Google Scholar 

  47. Björgvinsson BM, Heinze T, Roesky HW, Pauer F, Stalke D, Sheldrick GM (1991) Synthesis and structure of the first tellurium(III) radical cation. Angew Chem Int Ed 30:1677–1678

    Article  Google Scholar 

  48. Lin TP, Gabbai FP (2012) Two-electron redox chemistry at the dinuclear core of a TePt platform: chlorine photoreductive elimination and isolation of a Te(V)Pt(I) complex. J Am Chem Soc 134:12230–12238

    Article  Google Scholar 

  49. Singh HB, Mcwhinnie WR (1984) The electrochemical oxidation of 3,4-benzo-l-telluracyclopentane. J Organomet Chem 264:305–307

    Article  Google Scholar 

  50. Schmid GH, Garratt DG (1975) The preparation of seleniranium and selenirenium ions. Tetrahedron Lett 16:3991–3994

    Article  Google Scholar 

  51. Lindgren B (1974) Nucleophilic substitution reactions of β-substituted selenides. Tetrahedron Lett 15:4347–4350

    Article  Google Scholar 

  52. Schmid GH, Garratt DG (1974) The isolation of an episelenurane from the reaction of 4-tolueneselenenyl chloride with ethylene. Can J Chem 52:1027–1028

    Article  Google Scholar 

  53. Denmark SE, Kalyani D, Collins WR (2010) Preparative and mechanistic studies toward the rational development of catalytic, enantioselective selenoetherification reactions. J Am Chem Soc 132:15752–15765

    Article  Google Scholar 

  54. Wirth T, Fragale G, Spichty M (1998) Mechanistic course of the asymmetric methoxyselenenylation reaction. J Am Chem Soc 120:3376–3381

    Article  Google Scholar 

  55. Uehlin L, Fragale G, Wirth T (2002) New and efficient chiral selenium electrophiles. Chem Eur J 8:1125–1133

    Article  Google Scholar 

  56. Denmark SE, Collins WR, Cullen MD (2009) Observation of direct sulfenium and selenenium group transfer from thiiranium and seleniranium ions to alkenes. J Am Chem Soc 131:3490–3492

    Article  Google Scholar 

  57. Poleschner H, Seppelt K (2008) Selenirenium and tellurirenium ions. Angew Chem Int Ed 47:6461–6464

    Article  Google Scholar 

  58. Engesser TA, Lichtenthaler MR, Schleep M, Krossing I (2016) Reactive p-block cations stabilized by weakly coordinating anions. Chem Soc Rev 45:789–899

    Article  Google Scholar 

  59. Engesser TA, Hrobárik P, Trapp N, Eiden P, Scherer H, Kaupp M, Krossing I (2012) [TeX3]+ Cations stabilized by the weakly coordinating [Al(ORF)4] anion: FIR spectra, Raman spectra, and evaluation of an abnormal halogen dependence of the 125Te NMR chemical shifts. Chem Plus Chem 77:643–651 and references cited therein

    Google Scholar 

  60. Jeske J, du Mont W-W, Jones PG (1996) Dimeric triaryltelluronium new metastable tetramers arenetellurolates: of diaryltellurium. Angew Chem Int Ed 35:2653–2655

    Article  Google Scholar 

  61. Klapötke TM, Krumm B, Scherr M (2007) Bis{bis[2-(dimethylaminomethyl)phenyl]-hydroxytelluronium} hexafluorosilicate chloroform tetrasolvate. Acta Cryst E 63:o4189

    Article  Google Scholar 

  62. Srivastava K, Shah P, Singh HB, Butcher RJ (2011) Isolation and structural characterization of some aryltellurium halides and their hydrolyzed products stabilized by an intramolecular Te N interaction. Organometallics 30:534–546

    Article  Google Scholar 

  63. Gerding H, Houtgra H (1954) Investigation of the structure of the compounds TeCl4 AlCl3and SeCl4 AlCl3 by means of the Raman effect. Recl Trav Chim Pays-Bas 73:759–770

    Article  Google Scholar 

  64. Beattie IR, Chudzynska H (1967) The vibrational spectra of some chloro-complexes of sulphur, selenium, and tellurium in the (4+) oxidation state. J Chem Soc A 984–990. doi:10.1039/J19670000984

  65. Krebs B, Buss B, Altena D (1971) Die Krirtallstruktur von Trichlorotellur(lV)-tetrachloroaluminat TeCl3+, AlCl4−. Z Anorg Allg Chem 386:257–269

    Article  Google Scholar 

  66. Edwards AJ, Taylor P (1973) Fluoride crystal structures. Part XX1.trifluorotellurium(iv) μ-fluorobis[pentafluoroantimonate(v)]. J Chem Soc Dalton Trans 2150–2153. doi:10.1039/DT9730002150

  67. Passmore J, Richardson EK, Whidden TK, White PS (1980) The X-ray crystal structures of SeBr 3 SbF6 and TeBr3 AsF6. Can J Chem 58:851–857

    Article  Google Scholar 

  68. Passmore J, Sutherland G, White PS (1981) The synthesis and X-ray crystal structure of triiodotellurium(IV) hexafluoroarsenate(V), TeI3 AsF6. Can J Chem 59:2876–2878

    Article  Google Scholar 

  69. Collins MJ, Schrobilgen GJ (1985) Study of the OTeF5, donor properties of Te(OTeF5)4 by 75As and 125Te NMR spectroscopy. preparation and characterization of the [TeFex(OTeF5)3_x]+ cations, TeFx(OTeF5)4-x, AS(OTeF5)5, and [As(OTeF5)6]−1. Inorg Chem 24:2608–2614

    Article  Google Scholar 

  70. Cameron TS, Dionne I, Krossing I, Passmore J (2002) Reactions directed towards Sb(OTeF5) 6 salts of new tellurium cations: formation, FT-Raman spectrum and x-ray crystal structure of [Cl3Te-F-TeCl3][Sb(OTeF5)6] containing the µ-fluoro-bis[trichloro-tellurium(IV)] cation. Solid State Sci 4:1435–1441

    Article  ADS  Google Scholar 

  71. Freire-Erdbrügger C, Jentsch D, Jones PG, Schwarzmann E (1987) Preparation and crystal structure of [TeBr 3][AuBr4] 1/2 Br2, a compound with bromine of crystallization. Z Naturforsch B 42:1553–1555

    Article  Google Scholar 

  72. Beck J (1991) Tellurium cations by Lewis acid-base reactions: syntheses and crystal structures of (Te24+)(Zr2Br 210−) and (TeBr3p+)(Zr2Br9−). Chem Ber 124:677–681

    Article  Google Scholar 

  73. Beck J (1990) Synthese und Kristallstruktur von Te 2+4 (MoOCl4) 2−2 . Z Naturforsch B 45:1610–1614

    Google Scholar 

  74. Schulz-Lang E, Abram U, Strähle J, Lopez EMV (1998) Synthesis and crystal structure of [TeI3][GaI4] and [TeI3][InI4]. Z Anorg Allg Chem 624:999–1002

    Article  Google Scholar 

  75. Johnson JP, Murchie M, Passmore J, Tajik M, White PS, Wong CM (1987) The preparation of SeI3SbF6 and TeI3SbF6; the x-ray crystal structures of SBr 3 AsF6, SeI3 AsF6, SeI3 SbF6, and TeI3 SbF6; some considerations of the energetics of the formation of SBr3 AsF6 and SeI3 AsF6. Can J Chem 65:2744–2755

    Article  Google Scholar 

  76. Christian BH, Collins MJ, Gillespie RJ, Sawyer JF (1986) Preparations, Raman spectra, and crystal structures of (SC13) (SbC16), (SeCI3) (SbCI6), (SBr 1.2Cl1.8) (SbCl6), (TeCI3)(AICl4) (Triclinic Modification), (TeCI3)(SbF6), (TeC13)(AsF6), and (TeF3)2(SO4). Inorg Chem 25:777–788 and references cited therein

    Article  Google Scholar 

  77. Mason J (1987) Multinuclear NMR (Ed), Plenum Press, New York and references therein

  78. Kaupp M, Malkina OL, Malkin VG, Pyykkö P (1998) How do spin-orbit-induced heavy-atom effects on NMR chemical shifts function? validation of a simple analogy to spin-spin coupling by density functional theory (DFT) calculations on some iodo compounds. Chem Eur J 4:118–126

    Article  Google Scholar 

  79. Irgolic KJ (1974) The organic chemistry of tellurium. Gordon and Breach, New York, p 199 and references therein

  80. Oilunkaniemi R, Pietikäinen J, Laitinen RS, Ahlgrán M (2001) Cation-anion interactions in triphenyl telluronium salts. The crystal structures of (Ph3Te)2[MCl6] (M = Pt, Ir), (Ph3Te)[AuCl4], and (Ph3Te)(NO3) HNO3. J Organomet Chem 640:50–56

    Article  Google Scholar 

  81. Zhou Z-L, Huang Y-Z, Tang Y, Chen Z-H, Shi L-P, Jin X-L, Yang Q-C (1994) 125Te nuclear magnetic resonance study and x-ray crystal structures of organotelluronium salts. Organometallics 13:1575–1581

    Article  Google Scholar 

  82. Hirabayashi K, Nara Y, Shimizu T, Kamigata N (2004) Palladium-catalyzed Mizoroki-Heck-type reactions using telluronium salts. Chem Lett 33:1280–1281

    Article  Google Scholar 

  83. Lin TP, Gabbaï FP (2013) Telluronium ions as sigma-acceptor ligands. Angew Chem Int Ed 52:3864–3868

    Article  Google Scholar 

  84. Jones JS, Gabbaï FP (2016) Coordination and redox non-innocent behavior of hybrid ligands containing tellurium. Chem Lett 45:376–384

    Article  Google Scholar 

  85. Kumar NK, Baskar V (2015) Assembling anionic Sb(V)/(III) containing polyoxostibonates stabilized by triphenyltellurium cations. Dalton Trans 44:6358–6362

    Article  Google Scholar 

  86. Zhao H, Gabbai FP (2010) A bidentate Lewis acid with a telluronium ion as an anion-binding site. Nat Chem 2:984–990

    Article  Google Scholar 

  87. Lowry TM, Gilbert FL (1929) An optically active telluronium salt: phenyl-p-tolyl-rnethyltelluronium iodide. J Chem Soc 2867–2876

  88. Holliman FG, Mann FG (1945) The synthetic application of o-β-bromethylbenzyl bromide. Part V. The preparation and properties of thioisochroman, selenoisochroman, telluroisochroman, and of their optically active derivatives. J Chem Soc 37–44. doi:10.1039/JR9450000037

  89. Shimizu T, Urakubo T, Kamigata N (1996) Synthesis and absolute configuration of optically active telluronium salts. Chem Lett 25:297–298

    Article  Google Scholar 

  90. Zhang J, Saito S, Koizumi T (1998) Diastereoselective synthesis and stereochemical research of optically pure telluronium salts. J Org Chem 63:5423–5429

    Article  Google Scholar 

  91. Shimizu T, Sakurai R, Azami Y, Hirabayashi K, Kamigata N (2010) Isolation and racemization mechanism of optically active benzylmethylphenyltelluronium salts. Eur J Org Chem 2010(34):6556–6562

  92. Shimizu T, Urakubo T, Jin P, Kondo M, Kitagawa S, Kamigata N (1997) Crystal structures of optically active diastereomeric telluronium and selenonium salts anion-cation interactions in the crystalline state. J Organomet Chem 539:171–175 and references cited therein

    Article  Google Scholar 

  93. Ziolo RF, Titus DD (1976) Crystal data for triphenyl teiluronium pseudohalides. J Appl Crystallogr 9:506–507

    Article  Google Scholar 

  94. Ziolo RF, Pritchett K (1976) Synthesis and solid state characterization of triphenyltelluronium pseudohalides. J Organomet Chem 116:211–217

    Article  Google Scholar 

  95. Titus DD, Lee J-S, Ziolo RF (1976) The solid state structure of triphenyltelluronium cyanate-chloroform. J Organomet Chem 120:381–388

    Article  Google Scholar 

  96. Lee J-S, Titus DD, Ziolo RF (1976) X-ray structure of triphenyltelluronium thiocyanate: an oligomeric organotelluronium salt. J Chem Soc Chem Commun 501–502

  97. Lee J-S, Titus DD, Ziolo RF (1977) Structural characterization of the bioligomeric triphenyltelluronium thiocyanate salt, [(C6H5)3Te(NCS))4((C6H5)3Te(NCS)]2. Inorg Chem 16:2487–2492

    Article  Google Scholar 

  98. Klapötke TM, Krumm B, Mayer P, Polborn K, Ruscitti OP (2001) The reactivity of perfluoroaryltellurium(IV) dihalides towards cyanide, crystal structures of (C6F5)3TeCl and C6F5TeTeC6F5. J Fluor Chem 112:207–212

    Article  Google Scholar 

  99. Klapötke TM, Krumm B, Mayer P, Piotrowski H, Schwab I, Vogt M (2002) Synthesis and structures of triorganotelluronium pseudohalides. Eur J Inorg Chem 2701–2709

  100. du Mont W-W, Jeske J, Jones PG (2010) Soft-soft interactions of iodide and triiodide ions with triphenyltelluronium cations. Phosphorus Sulfur Silicon Relat Elem 185:1243–1249

    Article  Google Scholar 

  101. Fujihara H, Ishitani H, Takaguchi Y, Furukawa N (1995) Synthesis and x-ray structure of 1,8-bis(phenyltelluro)naphthalene and its peri tellurium-tellurium interaction. Chem Lett 24:571–572

    Article  Google Scholar 

  102. Knight FR, Randall RAM, Arachchige KSA, Wakefield L, Griffin JM, Ashbrook SE, Bühl M, Slawin AM, Woollins JD (2012) Noncovalent interactions in peri-substituted chalconium acenaphthene and naphthalene salts: a combined experimental, crystallographic, computational, and solid-state NMR study. Inorg Chem 51:11087–11097

    Article  Google Scholar 

  103. Engman L, Lind J, Merényi G (1994) Redox properties of diaryl chalcogenides and their oxides. J Phys Chem 98:3174–3182

    Article  Google Scholar 

  104. Gilbert FL, Lowry TM (1928) Electrometric titration of vernon’s α and β-dimethyltelluronium bases. J Chem Soc 1997–2010

  105. Beckmanna J, Dakternieksa D, Duthie A, Lewcenkoa NA, Mitchella C, Schürmann M (2005) The reactivity of bis(para-methoxyphenyl)telluroxide towards triflic acid and diphenylphosphinic acid. Theoretical considerations of the protonation and hydration process of diorganotelluroxanes. Z Anorg Allg Chem 631:1856–1862

    Article  Google Scholar 

  106. Beckmann J, Bolsinger J, Duthie A, Finke P (2011) New series of intramolecularly coordinated diaryltellurium compounds. Rational synthesis of the diarylhydroxytelluronium triflate [(8-Me2NC10H6)2Te(OH)](O3SCF3). Organometallics 31:238–245

    Article  Google Scholar 

  107. Klapötke TM, Krumm B, Scherr M (2007) Bis{bis[2-(dimethylaminomethyl)phenyl]- hydroxytelluronium} hexafluorosilicate chloroform tetrasolvate. Acta Cryst E 63:o4189

    Article  Google Scholar 

  108. Kobayashi K, Sato S, Horn E, Furukawa N (2000) Crystal structure of bis[2,6-{bis(dimethylamino)methyl}phenyl]-di-μ-oxoditellurium bis(hexafluorophosphate), [Te(C12H19N2)O]2(PF6)2. Z Kristallogr NCS 215:21–22

    Google Scholar 

  109. Lin TP, Gabbai FP (2013) Telluronium ions as sigma-acceptor ligands. Angew Chem Int Ed 52:3864–3868

    Article  Google Scholar 

  110. Kobayashi K, Deguchi N, Horn E, Furukawa N (1998) Insertion of an Oxygen atom between tellurium atoms upon oxidation of a diaryl telluride with NOBF4 or (CF3SO2)2O/O2: dicationic bis[diaryltellurium(iv)] oxide. Angew Chem Int Ed 37:984–986

    Article  Google Scholar 

  111. Kobayashi K, Deguchi N, Takahashi O, Tanaka K, Horn E, Kikuchi O, Furukawa N (1999) Nucleophilic addition of telluroxides to a cationic ditelluroxane: oligotelluroxanes. Angew Chem Int Ed 38:1638–1640

    Article  Google Scholar 

  112. Boyle PD, Godfrey SM (2001) The reactions of sulfur and selenium donor molecules with dihalogens and interhalogens. Coord Chem Rev 223:265–299

    Article  Google Scholar 

  113. Laur PH, Saberi-Niaki SM, Scheiter M, Englert CHU, Wang Y, Fleischhauer J (2005) Diaryl tellurium dihalides: from Te-tetracoordinated compounds to Te-tricoordinated molecular complexes. Phosphorus Sulfur Silicon Relat Elem 180:1035–1044

    Article  Google Scholar 

  114. Faoro E, den Oliveira GM, Lang ES, Pereira CB (2010) Synthesis and structural features of new aryltellurenyl iodides. J Organomet Chem 695:1480–1486

    Article  Google Scholar 

  115. Beckmann J, Bolsinger J, Duthie A, Finke P (2013) Diarylhalotelluronium(IV) cations [(8-Me2NC10H6)2TeX]+ (X = Cl, Br, I) stabilized by intramolecularly coordinating N-donor substituents. Dalton Trans 42:12193–12202

    Article  Google Scholar 

  116. Detty MR, Friedman AE, McMillan M (1995) Stepwise mechanism for oxidative addition of bromine to organoselenium(I1) and organotellurium(I1) compounds. Organometallics 13:5258–5262

    Article  Google Scholar 

  117. Detty MR, Williams AJ, Hewitt JM, McMillan M (1995) lH NMR exchange reactions in tellurium(IV) derivatives with cleavage of Te-N bonds. Organometallics 14:5258–5262

    Article  Google Scholar 

  118. Bolsinger J, Beckmann J (2014) Synthesis and structure of diarylhalotelluronium hexahalotellurates [(8-Me 2NC10H6)2TeX]2TeX6 (X = Cl, Br). Main Group Met Chem 37:159–162

    Article  Google Scholar 

  119. Musher JI (1969) The chemistry of hypervalent molecules. Angew Chem Int Ed 8:54–68

    Article  Google Scholar 

  120. Chivers T, Laitinen RS (2015) Tellurium: a maverick among the chalcogens. Chem Soc Rev 44:1725–1739

    Article  Google Scholar 

  121. Minoura M, Mukuda T, Sagami T, K-y Akiba (1999) Synthesis and characterization of a hypervalent tellurium cation, Ph5Te+: a stable nonclassical onium compound. J Am Chem Soc 121:10852–10853 and references cited therein

    Article  Google Scholar 

  122. Musher JI (1972) Some aspects of bonding and structure in hypervalent selenium and tellurium chemistry. Ann N Y Acad Sci 192:52–59

    Article  ADS  Google Scholar 

  123. Hellwinkel D (1972) Hypervalent organic derivatives of tellurium and selenium. Ann N Y Acad Sci 192:158–166

    Article  ADS  Google Scholar 

  124. Olah GA, Prakash GKS, Williams RE, Field LD, Wade K (1987) Hypercarbon chemistry. Wiley, New York

    Google Scholar 

  125. Olah GA, Rasul G (1997) From Kekulé’s tetravalent methane to five-, six-, and seven-coordinate protonated methanes. Acc Chem Res 30:245–250

    Article  Google Scholar 

  126. White ET, Tang J, Oka T (1999) CH5 +: the infrared spectrum observed. Science 284:135–137

    Article  ADS  Google Scholar 

  127. Minoura M, Mukuda T, Sagami T, K-y Akiba (2001) Synthesis and structure of pentaphenyltelluronium salts of perchlorate and tetrakis{3,5-bis(trifluoromethyl)phenyl}borate: hypervalent onium compounds. Heteroat Chem 12:380–384 and references cited therein

    Article  Google Scholar 

  128. Bondi A (1964) van der Waals volumes and radii. J Phys Chem 68:441–451

    Article  Google Scholar 

  129. Batsanov SS (2001) Van der Waals radii of elements. Inorg Mater 37:1031–1046

    Google Scholar 

  130. Pauling L (1994) Triethylsilyl cations. Science 263:983

    Article  ADS  Google Scholar 

  131. Hoffmann R, Howell JM, Muetterties EL (1972) Molecular orbital theory of pentacoordinate phosphorus. J Am Chem Soc 94:3047–3058

    Article  Google Scholar 

  132. Beauchamp AL, Bennett MJ, Cotton FA (1968) A reinvestigation of the crystal and molecular structure of pentaphenylantimony. J Am Chem Soc 90:6675–6680

    Article  Google Scholar 

  133. Miyasato M, Mukuda T, Minoura M, Yamamoto Y, K-y Akiba (2002) Coordination of trimethylphosphine with pentaphenyltelluronium salts. Phosphorus Sulfur Silicon Relat Elem 177:2043–2044

    Article  Google Scholar 

  134. K-y Akiba (2011) Studies on hypervalent compounds and synthetic work using heteroaromatic cations. Heteroat Chem 22:207–274

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Harkesh B. Singh.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gupta, A., Kumar, S. & Singh, H.B. Structural and Reactivity Aspects of Organoselenium and Tellurium Cations. Proc. Natl. Acad. Sci., India, Sect. A Phys. Sci. 86, 465–498 (2016). https://doi.org/10.1007/s40010-016-0301-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40010-016-0301-1

Keywords

Navigation