Bioinorganic Chemistry and Applications

Volume 2009, Article ID 347359, 11 pages

http://dx.doi.org/10.1155/2009/347359

Research Article

## Fine Structures of 8-G-1-(-) (G = H, Cl, and Br) in Crystals and Solutions: Ethynyl Influence and Y- and G-Dependences

Department of Material Science and Chemistry, Faculty of Systems Engineering, Wakayama University, 930 Sakaedani, Wakayama 640-8510, Japan

Received 18 January 2009; Revised 14 April 2009; Accepted 24 June 2009

Academic Editor: Govindasamy Mugesh

Copyright © 2009 Satoko Hayashi et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

#### Linked References

- W. Nakanishi, “Hypervalent chalcogen compounds,” in
*Handbook of Chalcogen Chemistry: New Perspectives in Sulfur, Selenium and Tellurium*, F. A. Devillanova, Ed., chapter 10.3, Royal Society of Chemistry, London, UK, 2006. View at Google Scholar - W. Nakanishi, S. Hayashi, and S. Toyota, “Structure of bis(8-(phenylselanyl)naphthyl)diselenide: first linear alignment of four Se atoms as a four-centre six-electron bond,”
*Chemical Communications*, no. 3, pp. 371–372, 1996. View at Google Scholar - W. Nakanishi, S. Hayashi, and H. Yamaguchi,
*Chemistry Letters*, no. 25, pp. 947–948, 1996. - W. Nakanishi, S. Hayashi, and S. Toyota, “Four-center six-electron interaction versus lone pair-lone pair interaction between selenium atoms in naphthalene peri positions,”
*Journal of Organic Chemistry*, vol. 63, no. 24, pp. 8790–8800, 1998. View at Publisher · View at Google Scholar - S. Hayashi and W. Nakanishi, “Novel substituent effect on ${}^{77}\text{S}\text{e}$ NMR chemical shifts caused by 4c–6e versus 2c–4e and 3c–4e in naphthalene peri positions: spectroscopic and theoretical study,”
*Journal of Organic Chemistry*, vol. 64, no. 18, pp. 6688–6696, 1999. View at Publisher · View at Google Scholar - W. Nakanishi, S. Hayashi, and T. Arai, “Linear alignment of four sulfur atoms in bis[(8-phenylthio)naphthyl] disulfide: contribution of linear ${\text{S}}_{4}$ hypervalent four-centre six-electron bond to the structure,”
*Chemical Communications*, no. 20, pp. 2416–2417, 2002. View at Google Scholar - W. Nakanishi, S. Hayashi, and N. Itoh, “First linear alignment of five C–$\text{Se}\cdots \text{O}\cdots $Se–C atoms in anthraquinone and 9-(methoxy)anthracene bearing phenylselanyl groups at 1,8-positions,”
*Chemical Communications*, vol. 9, no. 1, pp. 124–125, 2003. View at Publisher · View at Google Scholar - W. Nakanishi, S. Hayashi, and N. Itoh, “Extend hypervalent 5c–6e interactions: linear alignment of five C–$\text{Se}\cdots \text{O}\cdots $Se–C atoms in anthraquinone and 9-methoxyanthracene bearing arylselanyl groups at the 1,8-positions,”
*Journal of Organic Chemistry*, vol. 69, no. 5, pp. 1676–1684, 2004. View at Publisher · View at Google Scholar - W. Nakanishi, S. Hayashi, T. Furuta et al., “Extended hypervalent 5c–6e interactions: linear alignment of five C—$\text{Z}?\text{O}?\text{Z}$—C (Z = S, Se) atoms in anthraquinone and anthracene systems,”
*Phosphorus, Sulfur and Silicon and the Related Elements*, vol. 180, no. 5-6, pp. 1351–1355, 2005. View at Publisher · View at Google Scholar - W. Nakanishi, T. Nakamoto, S. Hayashi, T. Sasamori, and N. Tokitoh, “Atoms-in-molecules analysis of extended hypervalent five-center, six-electron (5c–6e) ${\text{C}}_{2}{\text{Z}}_{2}$O interactions at the 1,8,9-positions of anthraquinone and 9-methoxyanthracene systems,”
*Chemistry*, vol. 13, no. 1, pp. 255–268, 2007. View at Publisher · View at Google Scholar - W. Nakanishi, S. Hayashi, S. Yamaguchi, and K. Tamao, “First ${\text{Br}}_{4}$ four centre-six electron and ${\text{Se}}_{2}{\text{Br}}_{5}$ seven centre-ten electron bonds in nonionic bromine adducts of selenanthrene,”
*Chemical Communications*, vol. 10, no. 2, pp. 140–141, 2004. View at Google Scholar - G. C. Pimentel, “The bonding of trihalide and bifluoride ions by the molecular orbital method,”
*The Journal of Chemical Physics*, vol. 19, no. 4, pp. 446–448, 1951. View at Google Scholar - J. I. Musher, “The chemistry of hypervalent molecules,”
*Angewandte Chemie International Edition in English*, vol. 8, no. 1, pp. 54–68, 1969. View at Google Scholar - K.-Y. Akiba, Ed.,
*Chemistry of Hypervalent Compounds*, Wiley-VCH, New York, NY, USA, 1999. - W. Nakanishi, S. Hayashi, and T. Uehara, “Successive change in conformation caused by $p$-Y groups in 1-(MeSe)-8-(
*p*-${\text{YC}}_{6}{\text{H}}_{4}$Se)${\text{C}}_{10}{\text{H}}_{6}$: role of linear $\text{Se}\cdots \text{Se}$–C three-center-four-electron versus n(Se)$\cdots $n(Se) two-center-four-electron nonbonded interactions,”*Journal of Physical Chemistry A*, vol. 103, no. 48, pp. 9906–9912, 1999. View at Google Scholar - W. Nakanishi and S. Hayashi, “Structure of 1-(arylselanyl)naphthalenes. 2. G dependence in 8-G-1-(
*p*-${\text{YC}}_{6}{\text{H}}_{4}$Se)${\text{C}}_{10}{\text{H}}_{6}$,”*Journal of Organic Chemistry*, vol. 67, no. 1, pp. 38–48, 2002. View at Publisher · View at Google Scholar - R. A. Hayes and J. C. Martin, “Sulfurane chemistry,” in
*Organic Sulfur Chemistry: Theoretical and Experimental Advances*, F. Bernardi, I. G. Csizmadia, and A. Mangini, Eds., Elsevier, Amsterdam, The Netherlands, 1985. View at Google Scholar - W. Nakanishi, S. Hayashi, A. Sakaue, G. Ono, and Y. Kawada, “Attractive interaction caused by the linear $\text{F}\cdots \text{Se}$–C alignment in naphthalene peri positions,”
*Journal of the American Chemical Society*, vol. 120, no. 15, pp. 3635–3640, 1998. View at Publisher · View at Google Scholar - S. Scheiner, Ed.,
*Molecular Interactions. From van der Waals to Strongly Bound Complexes*, John Wiley & Sons, New York, NY, USA, 1997. - K.-D. Asmus, “Stabilization of oxidized sulfur centers in organic sulfides. Radical cations and odd-electron sulfur-sulfur bonds,”
*Accounts of Chemical Research*, vol. 12, no. 12, pp. 436–442, 1979. View at Google Scholar - W. K. Musker, “Chemistry of aliphatic thioether cation radicals and dications,”
*Accounts of Chemical Research*, vol. 13, no. 7, pp. 200–206, 1980. View at Google Scholar - W. Nakanishi, S. Hayashi, and T. Uehara, “Structure of 1-(arylselanyl)naphthalenes—Y dependence in 1-(
*p*-${\text{YC}}_{6}{\text{H}}_{4}$Se)${\text{C}}_{10}{\text{H}}_{7}$,”*European Journal of Organic Chemistry*, no. 20, pp. 3933–3943, 2001. View at Google Scholar - S. Hayashi, H. Wada, T. Ueno, and W. Nakanishi, “Structures of 1-(arylseleninyl)naphthalenes: O, G, and Y dependences in 8-G-1-[
*p*-${\text{YC}}_{6}{\text{H}}_{4}$Se(O)]${\text{C}}_{10}{\text{H}}_{6}$,”*Journal of Organic Chemistry*, vol. 71, no. 15, pp. 5574–5585, 2006. View at Publisher · View at Google Scholar - A. Kucsman and I. Kapovits, “Nonbonded sulfur-oxygen interaction,” in
*Organic Sulfur Chemistry: Theoretical and Experimental Advances*, F. Bernardi, I. G. Csizmadia, and A. Mangini, Eds., Elsevier, Amsterdam, The Netherlands, 1985. View at Google Scholar - R. S. Glass, S. W. Andruski, and J. L. Broeker, “Geometric effects in sulfur lone pair interactions,” in
*Reviews on Hetaroacom Chemistry*, S. Oae, Ed., vol. 1, pp. 31–45, MYU, Tokyo, Japan, 1988. View at Google Scholar - R. S. Glass, S. W. Andruski, J. L. Broeker, H. Firouzabadi, L. K. Steffen, and G. S. Wilson, “Sulfur-sulfur lone pair and sulfur-naphthalene interactions in naphtho[1,8-
*b,c*]-1,5-dithiocin,”*Journal of the American Chemical Society*, vol. 111, no. 11, pp. 4036–4045, 1989. View at Google Scholar - R. S. Glass, L. Adamowicz, and J. L. Broeker, “Theoretical studies on transannular $\text{S}\cdots \text{S}$ interactions in geometrically constrained 1,5-dithiocane derivatives,”
*Journal of the American Chemical Society*, vol. 113, no. 4, pp. 1065–1072, 1991. View at Google Scholar - N. Furukawa, “Studies on dichalcogena dications of 2-center-2-electron and 3-center-4-electron bonds: isolation and intermediary formation,”
*Bulletin of the Chemical Society of Japan*, vol. 70, no. 11, pp. 2571–2591, 1997. View at Google Scholar - N. Furukawa, K. Kobayashi, and S. Sato, “Transannular and intermolecular interactions between chalcogen atoms: syntheses and properties of dichalcogena dications and trichalcogena hypervalent dications,”
*Journal of Organometallic Chemistry*, vol. 611, no. 1-2, pp. 116–126, 2000. View at Google Scholar - W. Nakanishi, “Facile C–Se and C–S bond cleavages in diorganyl selenides and sulfides by iodine,”
*Chemistry Letters*, vol. 22, no. 12, pp. 2121–2122, 1993. View at Google Scholar - M. Iwaoka, S. Takemoto, M. Okada, and S. Tomoda, “Statistical characterization of nonbonded $\text{S}\cdots \text{O}$ interactions in proteins,”
*Chemistry Letters*, vol. 30, no. 2, pp. 132–133, 2001. View at Google Scholar - M. Iwaoka, S. Takemoto, M. Okada, and S. Tomoda, “Weak nonbonded $\text{S}\cdots \text{X}$ (X = O, N, and S) interactions in proteins. statistical and theoretical studies,”
*Bulletin of the Chemical Society of Japa*, vol. 75, no. 7, pp. 1611–1625, 2002. View at Google Scholar - G. R. Desiraju, “Supramolecular synthons in crystal engineering—a new organic synthesis,”
*Angewandte Chemie International Edition in English*, vol. 34, no. 21, pp. 2311–2327, 1995. View at Google Scholar - V. Lippolis and F. Isaia, “Charge-transfer (C.-T.) adducts and related compound,” in
*Handbook of Chalcogen Chemistry: New Perspectives in Sulfur, Selenium and Tellurium*, F. A. Devillanova, Ed., chapter 8.2, Royal Society of Chemistry, London, UK, 2006. View at Google Scholar - C. Rêthorê, M. Fourmiguê, and N. Avarvari, “Tetrathiafulvalene based phosphino-oxazolines: a new family of redox active chiral ligands,”
*Chemical Communications*, vol. 10, no. 12, pp. 1384–1385, 2004. View at Google Scholar - C. Rêthorê, M. Fourmiguê, and N. Avarvari, “Tetrathiafulvalene-hydroxyamides and -oxazolines: hydrogen bonding, chirality, and a radical cation salt,”
*Tetrahedron*, vol. 61, no. 46, pp. 10935–10942, 2005. View at Publisher · View at Google Scholar - C. Rêthorê, N. Avarvari, E. Canadell, P. Auban-Senzier, and M. Fourmigué, “Chiral molecular metals: syntheses, structures, and properties of the ${{\text{ASF}}_{6}}^{-}$ salts of racemic (±)-, (R)-, and (S)-tetrathiafulvalene-oxazoline derivatives,”
*Journal of the American Chemical Society*, vol. 127, no. 16, pp. 5748–5749, 2005. View at Publisher · View at Google Scholar - T. Suzuki, H. Fujii, Y. Yamashita et al., “Clathrate formation and molecular recognition by novel chalcogen-cyano interactions in tetracyanoquinodimethanes fused with thiadiazole and selenadiazole rings,”
*Journal of the American Chemical Society*, vol. 114, no. 8, pp. 3034–3043, 1992. View at Google Scholar - M. Turbiez, P. Frêre, M. Allain, C. Videlot, J. Ackermann, and J. Roncali, “Design of organic semiconductors: tuning the electronic properties of $\pi $-conjugated oligothiophenes with the 3,4-ethylenedioxythiophene (EDOT) building block,”
*Chemistry: A European Journal*, vol. 11, no. 12, pp. 3742–3752, 2005. View at Publisher · View at Google Scholar - A. F. Cozzolino, I. Vargas-Baca, S. Mansour, and A. H. Mahmoudkhani, “The nature of the supramolecular association of 1,2,5-chalcogenadiazoles,”
*Journal of the American Chemical Society*, vol. 127, no. 9, pp. 3184–3190, 2005. View at Publisher · View at Google Scholar - G. Mugesh, A. Panda, H. B. Singh, N. S. Punekar, and R. J. Butcher, “Diferrocenyl diselenides: excellent thiol peroxidase-like antioxidants,”
*Chemical Communications*, no. 20, pp. 2227–2228, 1998. View at Google Scholar - G. Mugesh, A. Panda, H. B. Singh, N. S. Punekar, and R. J. Butcher, “Glutathione peroxidase-like antioxidant activity of diaryl diselenides: a mechanistic study,”
*Journal of the American Chemical Society*, vol. 123, no. 5, pp. 839–850, 2001. View at Publisher · View at Google Scholar - J. E. Drake, M. B. Hursthouse, M. Kulcsar, M. E. Light, and A. Silvestru, “Hypervalent tellurium compounds containing Te-N interactions. Mononuclear and polynuclear derivatives,”
*Phosphorus, Sulfur and Silicon and Related Elements*, vol. 168-169, no. 1, pp. 293–296, 2001. View at Google Scholar - J. E. Drake, M. B. Hursthouse, M. Kulcsar, M. E. Light, and A. Silvestru, “Hypervalent tellurium compounds containing $\text{N}\to \text{Te}$ intramolecular interactions,”
*Journal of Organometallic Chemistry*, vol. 623, no. 1-2, pp. 153–160, 2001. View at Google Scholar - G. Mugesh, A. Panda, S. Kumar, S. D. Apte, H. B. Singh, and R. J. Butcher, “Intramolecularly coordinated diorganyl ditellurides: thiol peroxidase-like antioxidants,”
*Organometallics*, vol. 21, no. 5, pp. 884–892, 2002. View at Publisher · View at Google Scholar - J. R. Anacona, J. Gómez, and D. Loroño, “Two polymorphs of bis(2-bromophenyl) disulfide,”
*Acta Crystallographica Section C*, vol. 59, no. 5, pp. o277–o280, 2003. View at Publisher · View at Google Scholar - G. Mugesh, H. B. Singh, and R. J. Butcher, “Synthesis and structural characterization of monomeric zinc(II), cadmium(II), and mercury(II) arenethiolates with a chelating oxazoline ligand,”
*European Journal of Inorganic Chemistry*, no. 8, pp. 1229–1236, 1999. View at Google Scholar - G. Mugesh, H. B. Singh, and R. J. Butcher, “Synthesis and characterization of monomeric tellurolato complexes of zinc and cadmium: crystal and molecular structure of bis[2-(4,4-dimethyl-2-oxazolinyl)phenyl]ditelluride,”
*Journal of Organometallic Chemistry*, vol. 577, no. 2, pp. 243–248, 1999. View at Google Scholar - D. Shimizu, N. Takeda, and N. Tokitoh, “Unusual carbon-sulfur bond cleavage in the reaction of a new type of bulky hexathioether with a zerovalent palladium complex,”
*Chemical Communications*, no. 2, pp. 177–179, 2006. View at Publisher · View at Google Scholar - W. Nakanishi, S. Hayashi, S. Morinaka, T. Sasamori, and N. Tokitoh, “Extended hypervalent ${\text{E}}^{\prime}\cdots \text{E}$–$\text{E}\cdots {\text{E}}^{\prime}$ 4c–6e (E, ${\text{E}}^{\prime}=\text{Se}$, S) interactions: structure, stability and reactivity of 1-(8-$\text{P}\text{h}{\text{E}}^{\prime}{\text{C}}_{10}{\text{H}}_{6}$)EE(${\text{C}}_{10}{\text{H}}_{6}{\text{E}}^{\prime}\text{Ph-}{8}^{\prime}$)-${1}^{\prime}$,”
*New Journal of Chemistry*, vol. 32, no. 11, pp. 1881–1889, 2008. View at Publisher · View at Google Scholar - P. J. Stang and F. Diederich, Eds.,
*Modern Acetylenic Chemistry*, Wiley-VCH, Weinheim, Germany, 1995. - F. Diederich, P. J. Stang, and R. R. Tykwinski, Eds.,
*Acetylene Chemistry: Chemistry, Biology, and Material Science*, Wiley-VCH, Weinheim, Germany, 2005. - A. J. Zucchero, J. N. Wilson, and U. H. F. Bunz, “Cruciforms as functional fluorophores: response to protons and selected metal ions,”
*Journal of the American Chemical Society*, vol. 128, no. 36, pp. 11872–11881, 2006. View at Publisher · View at Google Scholar - E. L. Spitler, L. D. Shirtcliff, and M. M. Haley, “Systematic structure-property investigations and ion-sensing studies of pyridine-derivatized donor/acceptor tetrakis(arylethynyl)benzenes,”
*Journal of Organic Chemistry*, vol. 72, no. 1, pp. 86–96, 2007. View at Publisher · View at Google Scholar - H. Hinrichs, A. J. Boydston, P. G. Jones et al., “Phane properties of [2.2]paracyclophane/dehydrobenzoannulene hybrids,”
*Chemistry: A European Journal*, vol. 12, no. 27, pp. 7103–7115, 2006. View at Publisher · View at Google Scholar - J. A. Marsden and M. M. Haley, “Carbon networks based on dehydrobenzoannulenes. 5. Extension of two-dimensional conjugation in graphdiyne nanoarchitectures,”
*Journal of Organic Chemistry*, vol. 70, no. 25, pp. 10213–10226, 2005. View at Publisher · View at Google Scholar - Y. Jiang, D. Perahia, Y. Wang, and U. H. F. Bunz, “Side chain vs main chain. Who dominates? A polyester-grafted poly(
*p*-phenyleneethynylene) with two different morphologies,”*Macromolecules*, vol. 39, no. 15, pp. 4941–4944, 2006. View at Publisher · View at Google Scholar - K. Tahara, S. Furukawa, H. Uji-i et al., “Two-dimensional porous molecular networks of dehydrobenzo[12]annulene derivatives via alkyl chain interdigitation,”
*Journal of the American Chemical Society*, vol. 128, no. 51, pp. 16613–16625, 2006. View at Publisher · View at Google Scholar - A. Nomoto, M. Sonoda, Y. Yamaguchi, T. Ichikawa, K. Hirose, and Y. Tobe, “A clue to elusive macrocycles: unusually facile, spontaneous polymerization of a hexagonal diethynylbenzene macrocycle,”
*Journal of Organic Chemistry*, vol. 71, no. 1, pp. 401–404, 2006. View at Publisher · View at Google Scholar - E. E. Nesterov, Z. Zhu, and T. M. Swager, “Conjugation enhancement of intramolecular exciton migration in poly(p-phenylene ethynylene)s,”
*Journal of the American Chemical Society*, vol. 127, no. 28, pp. 10083–10088, 2005. View at Publisher · View at Google Scholar - A. Orita, T. Nakano, D. L. An, K. Tanikawa, K. Wakamatsu, and J. Otera, “Metal-assisted assembly of pyridine-containing arylene ethynylene strands to enantiopure double helicates,”
*Journal of the American Chemical Society*, vol. 126, no. 33, pp. 10389–10396, 2004. View at Publisher · View at Google Scholar - A. Orita, D. L. An, T. Nakano, J. Yaruva, N. Ma, and J. Otera, “Sulfoximine version of double elimination protocol for synthesis of chiral acetylenic cyclophanes,”
*Chemistry: A European Journal*, vol. 8, no. 9, pp. 2005–2010, 2002. View at Publisher · View at Google Scholar - D. B. Werz and R. Gleiter, “Polyalkynes capped by sulfur and selenium,”
*Journal of Organic Chemistry*, vol. 68, no. 24, pp. 9400–9405, 2003. View at Publisher · View at Google Scholar - S. Husebye, E. A. Meyers, R. A. Zingaro, A. L. Braga, J. V. Comasseto, and N. Petragnani, “The structure of triphenyl[$\alpha $-(phenylseleno)phenacylidene]phosphorane,”
*Acta Crystallographica Section C*, vol. 42, no. 12, pp. 90–94, 1986. View at Publisher · View at Google Scholar - P. C. Bell, W. Skranc, X. Formosa, J. O'Leary, and J. D. Wallis, “Interactions between alkynes and methoxy or dimethylamino groups in peri-naphthalene systems,”
*Journal of the Chemical Society, Perkin Transactions 2*, no. 5, pp. 878–886, 2002. View at Google Scholar - K. Yamane, S. Hayashi, W. Nakanishi, T. Sasamori, and N. Tokitoh, “Fine structures of 1-(arylethynylselanyl)naphthalenes: characteristic features brought by the ethynylselanyl group,”
*Polyhedron*, vol. 27, no. 11, pp. 2478–2486, 2008. View at Publisher · View at Google Scholar - K. Yamane, S. Hayashi, W. Nakanishi, T. Sasamori, and N. Tokitoh, “Fine structures of 8-G-1-(arylethynylselanyl)naphthalenes (G = H, Cl, Br): factors to control the linear alignment of five $\text{G}\cdots \text{Se\u2013C}$$\equiv $C–${\text{C}}_{\text{Ar}}$ atoms in crystals and the behavior in solution,”
*Polyhedron*, vol. 27, no. 18, pp. 3557–3566, 2008. View at Publisher · View at Google Scholar - W. Nakanishi and S. Hayashi, “On the factors to determine ${}^{77}\text{S}\text{e}$
NMR chemical shifts of organic selenium compounds: application of GIAO magnetic schielding tensor to the ${}^{77}\text{S}\text{e}$ NMR spectroscopy,”
*Chemistry Letters*, no. 6, pp. 523–524, 1998. View at Google Scholar - A. Altomare, M. C. Burla, M. Camalli et al., “SIR97: a new tool for crystal structure determination and refinement,”
*Journal of Applied Crystallography*, vol. 32, no. 1, pp. 115–119, 1999. View at Google Scholar - G. M. Sheldrick,
*SHELXS 97, Program for Solving Crystal Structures*, University of Göttingen, Göttingen, Germany, 1997. - M. C. Burla, R. Caliandro, M. Camalli et al., “SIR2004: an improved tool for crystal structure determination and refinement,”
*Journal of Applied Crystallography*, vol. 38, no. 2, pp. 381–388, 2005. View at Publisher · View at Google Scholar - G. M. Sheldrick,
*SHELXL 97, Program for Structure Refinement*, University of Göttingen, Göttingen, Germany, 1997. - W. Nakanishi, S. Hayashi, D. Shimizu, and M. Hada, “Orientational effect of aryl groups on ${}^{77}\text{S}\text{e}$ NMR chemical shifts: experimental and theoretical investigations,”
*Chemistry: A European Journal*, vol. 12, no. 14, pp. 3829–3846, 2006. View at Publisher · View at Google Scholar - S. Hayashi, K. Yamane, and W. Nakanishi, “Orientational effect of aryl groups in aryl selenides: how can ${}^{1}\text{H}$ and ${}^{13}\text{C}$ NMR chemical shifts clarify the effect?”
*Journal of Organic Chemistry*, vol. 72, no. 20, pp. 7587–7596, 2007. View at Publisher · View at Google Scholar