ARTICLES
2.14 (s, 3H), 2.21 (s, 3H), 2.27 (s, 3H), 2.72 (dd, 3H, JH–F ¼ 2.4 Hz JH–Te ¼ 16.3 Hz),
21. Hudnall, T. W., Kim, Y.-M., Bebbington, M. W. P., Bourissou, D. & Gabba¨ı, F. P.
Fluoride ion chelation by a bidentate phosphonium/borane Lewis acid. J. Am.
Chem. Soc. 130, 10890–10891 (2008).
22. Kim, Y., Zhao, H. & Gabba¨ı, F. P. Sulfonium boranes for the selective capture of
cyanide ions in water. Angew. Chem. Int. Ed. 48, 4957–4960 (2009).
23. Metrangolo, P. & Resnati, G. Halogen bonding: a paradigm in supramolecular
chemistry. Chem. Eur. J. 7, 2511–2519 (2001).
24. Sudha, N. & Singh, H. B. Intramolecular coordination in tellurium chemistry.
Coord. Chem. Rev. 135, 469–515 (1994).
25. Burling, F. T. & Goldstein, B. M. Computational studies of nonbonded sulfur–
oxygen and selenium–oxygen interactions in the thiazole and selenazole
nucleosides. J. Am. Chem. Soc. 114, 2313–2320 (1992).
6.60 (s, 1H, Mes-CH), 6.72 (s, 2H, Mes-CH), 6.75 (s, 1H, Mes-CH), 7.15 (t, 1H,
JH–H ¼ 7.6 Hz, nap-CH), 7.27 (d, 1H, JH–H ¼ 8.4 Hz, nap-CH), 7.36 (t, 1H, JH–H
¼
7.6 Hz, nap-CH), 7.46–7.53 (m, 5H, ph-CH), 7.64 (d, 1H, JH–H ¼ 7.6 Hz, nap-CH),
7.70 (d, 1H, JH–H ¼ 6.8 Hz, nap-CH), 7.94 (d, 1H, JH–H ¼ 8.0 Hz, nap-CH);
13C NMR (100 MHz, CDCl3) d 13.06 (d, Te–CH3, JC–F ¼ 11 Hz), 20.9, 21.0, 24.2
(d, Mes-CH3, JC–F ¼ 7.3 Hz), 24.3, 24.8, 25.6, 123.7, 123.9, 126.7, 127.1, 127.8, 128.6,
129.1, 129.7, 129.9, 130.1, 130.5, 131.3, 132.9, 133.2, 134.8, 134.8, 135.3, 136.5, 136.5,
139.0, 141.0, 141.0, 142.1, 142.2, 142.3, 144.6; 11B NMR (128 MHz, d6-acetone) d þ
10.9 (bs); 19F NMR (375.9 MHz, CDCl3) d 2 130.4 (d, JTe–F ¼ 940 Hz); 125Te NMR
(126 MHz, CDCl3) d 713 (d, JTe–F ¼ 940 Hz). Calculated for C35H36BFTe: C, 68.46;
H, 5.91; found: C, 68.66; H, 5.94.
26. Gleiter, R., Werz, D. B. & Rausch, B. J. A world beyond hydrogen bonds?
Chalcogen–chalcogen interactions yielding tubular structures. Chem. Eur. J. 9,
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Fluoride ion-binding studies. A solution of [1]OTf (3 ml, 6.73 × 1025 M,
methanol) was placed in the cuvette and titrated with incremental amounts of
fluoride anions by the addition of a solution of KF in MeOH (0.3159 M). The
absorbance was monitored at l ¼ 353 nm (1 ¼ 12,800 for [1]OTf and 1 ¼ 3,750 for
1-F). The experimental data obtained were fitted to a 1:1 binding isotherm, which
indicated that the fluoride binding constant of [1]OTf is equal to 750 (+100) M21
in MeOH.
28. Tripathi Santosh, K. et al. o-Hydroxylmethylphenylchalcogens: synthesis,
. . .
intramolecular nonbonded chalcogen OH interactions, and glutathione
peroxidase-like activity. J. Org. Chem. 70, 9237–9247 (2005).
. . .
29. Hayashi, S. & Nakanishi, W. Noncovalent Z Z (Z¼O, S, Se, and Te)
interactions: how do they operate to control fine structures of
1,8-dichalcogene-substituted naphthalenes? Bull. Chem. Soc. Jpn 81,
1605–1615 (2008).
Received 11 February 2010; accepted 12 August 2010;
published online 26 September 2010
30. Lommerse, J. P. M., Stone, A. J., Taylor, R. & Allen, F. H. The nature and
geometry of intermolecular interactions between halogens and oxygen or
nitrogen. J. Am. Chem. Soc. 118, 3108–3116 (1996).
31. Chandrasekhar, V. & Thirumoorthi, R. Halide-capped tellurium-containing
macrocycles. Inorg. Chem. 48, 10330–10337 (2009).
32. Klapo¨tke, T. M., Krumm, B. & Scherr, M. Synthesis and structures of
triorganochalcogenium (Te, Se, S) dinitramides. Eur. J. Inorg. Chem.
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33. Naumann, D., Tyrra, W., Hermannn, R., Pantenburg, I. & Wickleder, M. S.
Syntheses and properties of tetrakis(pentafluorophenyl)tellurium, Te(C6F5)4,
and related compounds – single crystal structures of tris(pentafluoro-
phenyl)tellurium bromide, Te(C6F5)3Br, tris(pentafluorophenyl)tellurium
trifluoromethanesulfonate, [Te(C6F5)3][OSO2CF3], and bis(pentafluorophenyl)
tellurium oxide, Te(C6F5)2O. Z. Anorg. Allg. Chem. 628, 833–842 (2002).
34. Sato, S., Kondo, N., Horn, E. & Furukawa, N. Monooxytellurane(IV) derivatives
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carboxylate compounds. Organometallics 17, 1897–1900 (1998).
35. Hoefelmeyer, J. D. & Gabba¨ı, F. P. Synthesis of 1,8-diborylnaphthalenes by the
ring-opening reaction of a new anionic boron-bridged naphthalene derivative.
Organometallics 21, 982–985 (2002).
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