Abstract
The oxidation of organochalcogen compounds to their corresponding radical cations and dications is described. The importance of through space and ‘secondary’ interactions in influencing this oxidation chemistry is illustrated in a number of cases.
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Notes
- 1.
These model studies are challenging in their own right but further complicated by β-amyloid polymorphism [136].
- 2.
Interestingly this model has been supplanted by one in which Met-35 is directed away from the hydrophobic interior of the peptide (containing the side-chain of Phe-19) toward the exterior where it is close to a second Met residue of another peptide in the oligomer. If oxidation of Met-35 is important in the pathogenesis of Alzheimer’s disease, this suggests the possibility of interaction between the two methionine sulfur atoms. As mentioned above, 1, 5-dithiocane 8, X = Y = S reduces Cu(II).
References
Krossing I (2007) In: Devillanova FA (ed) Handbook of chalcogen chemistry. RSC Publishing, Cambridge; chapter 7.1
Cameron TS, Deeth RJ, Dionne I, Du H, Jenkins HDB, Krossing I, Passmore J, Roobottom HK (2000) Inorg Chem 39:5614–5631
Glass RS (2002) Spec Chem Mag 22:34–36
Glass RS (1999) Top Curr Chem 205:1–87
Detty MR, Logan ME (2004) Adv Phys Org Chem 39:79–145
Baird NC (1977) J Chem Educ 54:291–293
Clark T (1990) In: Chatgilialogu C, Asmus K-D (eds) Sulfur-centered reactive intermediates in chemistry and biology, vol 197, NATO ASI Ser A. Plenum, New York, pp 13–18
Stowasser R, Glass RS, Hoffmann R (1999) J Chem Soc Perkin Trans 2:1559–1561
Asmus K-D (2001) In: Jonah CD, Rao DSM (eds) Radiation chemistry: present status and future trends. Elsevier, Amsterdam, pp 341–393
Nakayama N, Takahashi O, Kikuchi O, Furukawa N (2001) J Mol Struct THEOCHEM 542:215–226
Maity DK (2002) J Am Chem Soc 124:8321–8328
Fourré I, Silvi B (2007) Heteroatom Chem 18:135–160
King JE, Illies AJ (2003) Int J Mass Spectrom 228:429–437
King JE, Illies AJ (2004) J Phys Chem A 108:3581–3585
Mishra B, Priyadarsini KJ, Mohan H (2006) J Phys Chem A 110:1894–1900
Mishra B, Sharma A, Naumov S, Priyadarsini KI (2009) J Phys Chem B 113:7709–7715
Naumov S, Bonifacic M, Glass RS, Asmus K-D (2009) Res Chem Intermed 35:479–496
Asmus K-D (1990) In: Chatgilialoglu C, Asmus K-D (eds) Sulfur-centered reactive intermediates in chemistry and biology. Plenum Press, New York, pp 155–172
von Sonntag C, Schuchman H-P (1980) In: Patai S (ed) The chemistry of ethers, crown ethers, hydroxyl groups, and their sulphur analogues, vol Pt 2, Suppl E. Wiley, Chichester; chapter 24
Asmus K-D (1984) Meth Enzymol 105:167–178
von Sonntag C (1987) The chemical basis of radiation biology. Taylor and Francis, London
Waltz WL (1988) In: Fox MA, Chanon M (eds) Photoinduced electron transfer, vol Pt B. Elsevier, Amsterdam, pp 57–109
Takamuku S, Yamamoto Y (1991) In: Tabata Y (ed) Pulse radiolysis. CRC Press, Boca Raton; chapter 18
Pienta NJ (1988) In: Fox MA, Chanon M (eds) Photoinduced electron transfer, vol Pt C. Elsevier, Amsterdam, pp 421–486
Kavarnos GJ (1993) Fundamentals of photoinduced electron transfer. Verlag Chemie, New York
van de Sande CC (1983) In: Patai S (ed) The chemistry of ethers, crown ethers, hydroxyl groups, and their sulphur analogues, vol Pt 1. Wiley, Chichester; chapter 7
Nibbering NMM, Ingermann S, de Kooning LJ (1996) In: Baer T, Ng CY, Powis I (eds) The structure, energetics, dynamics of organic ions. Wiley, New York, pp 283–290
Symons MCR (1984) Chem Soc Rev 13:393–439
Lund A, Shiotani M (eds) (1991) Radical ion systems properties in condensed phases. Kluwer, Dordrecht
Nenajedenko VG, Schevchenko NE, Balenkova ES, Alabugin IV (2007) In: Devillanova FA (ed) Handbook of chalcogen chemistry. RSC Publishing, Cambridge; chapter 7.2
Westgate TD, Skabara PJ (2007) In: Devillanova FA (ed) Handbook of chalcogen chemistry. RSC Publishing, Cambridge; chapter 12.2
Coffen DL, Chambers JQ, Williams DR, Garrett PE, Canfield ND (1971) J Am Chem Soc 93:2258–2268
Ferraris J, Cowan DO, Walatka V Jr, Perlstein JH (1973) J Am Chem Soc 95:948–949
Bechgaard K, Carneiro K, Rasmussen FG, Olsen M, Rindorf G, Jacobsen CS, Pedersen HJ, Scott JC (1981) J Am Chem Soc 103:2440–2442
Williams JM, Ferraro JR, Thorn RJ, Carlson KD, Geiser U, Wang HH, Kini AM, Whangbo M-H (1992) Organic superconductors. Prentice Hall, Englewood Cliffs
Ishiguro T, Yamaji K, Saito G (1998) Organic superconductors, 2nd edn. Springer, Berlin
Mori T, Kawamoto T, Bando Y, Noda B, Wada H, Matsuzawa T, Taguchi T, Katsuhara M, Aoyagi I, Kambayashi T, Ishikawa K, Takezoe H, Uji S, Takimaya K, Otsubo T (2007) In: Saito G, Wudl F, Haddon RC, Tanigaki K, Enoki T, Katz HE, Maesato M (eds) Multifunctional conducting molecular materials. RSC Publishing, Cambridge, pp 15–22
Gao X, Qiu W, Liu Y, Yu G, Zhu D (2008) Pure Appl Chem 80:2405–2423
Perepichka IF, Perepichka DF (eds) (2009) Handbook of thiophene-based materials. Wiley-VCH, Chichester
Heeger AJ (2001) Angew Chem Int Ed 40:2591–2611
Farchioni R, Grosso G (eds) (2001) Organic electronic materials. Berlin, Springer
Roncali J (2005) Chem Soc Rev 34:483–495
Kim JY, Lee K, Coates NE, Moses D, Nguyen T-Q, Dante M, Heeger AJ (2007) Science 317:222–225
Günes S, Neugebauer H, Sariciftci NS (2007) Chem Rev 107:1324–1338
Thompson BC, Fréchet JMJ (2008) Angew Chem Int Ed 47:58–77
Perepichka IF, Perepichka DF, Meng H, Wudl F (2005) Adv Mater 17:2281–2305
Grimsdale AC, Chan KL, Martin RE, Jokisz PG, Holmes AB (2009) Chem Rev 109:897–1091
Murphy AR, Fréchet JMJ (2007) Chem Rev 107:1066–1096
Patra A, Wijsboom YH, Zade SS, Li M, Sheynin Y, Leitus G, Bendikov M (2008) J Am Chem Soc 130:6734–6736
Patra A, Bendikov M (2010) J Mater Chem 20:422–433
Patra A, Wijsboom YH, Leitus G, Bendikov M (2009) Org Lett 11:1487–1490
Cordes M, Giese B (2009) Chem Soc Rev 38:892–901
Wang M, Gao J, Müller P, Giese B (2009) Angew Chem Int Ed 48:4232–4234
Giese B, Wang M, Gao J, Stotlz M, Müller P, Graber M (2009) J Org Chem 74:3621–3625
Glass RS, Hug GL, Schöneich C, Wilson GS, Kuznetsova L, Lee T-M, Ammam M, Lorance E, Nauser T, Nichol GS, Yamamoto T (2009) J Am Chem Soc 131:13791–13805
Schöneich C, Pogocki D, Wisniowski P, Hug GL, Bobrowski K (2000) J Am Chem Soc 122:10224–10225
Schöneich C, Pogocki D, Hug GL, Bobrowski K (2003) J Am Chem Soc 125:13700–13713
Prelog V, Traynham JG (1963) In: de Mayo P (ed) Molecular rearrangements. Interscience, NewYork, pp 593–615
Cope AC, Martin MM, McKervey MA (1966) Quart Rev Chem Soc 20:119–152
Roberts AA, Anderson CB (1969) Tetrahedron Lett 10:3883–3885
Kirchen RP, Sorensen TS (1979) J Am Chem Soc 101:3240–3243
Buzek P, Schleyer PVR, Vancik H, Sunko DE (1991). Chem Commun: 1538–1540
Galasso V (1998) Int J Quantum Chem 170:313–320
Leonard NJ (1979) Acc Chem Res 12:423–429
Musker WK, Wolford TL (1976) J Am Chem Soc 98:3055–3056
Musker WK, Wolford TL, Roush PD (1978) J Am Chem Soc 100:6416–6421
Musker WK (1980) Acc Chem Res 13:200–206
Wilson GS, Swanson DD, Klug JT, Glass RS, Ryan MD, Musker WK (1979) J Am Chem Soc 101:1040–1042
Ryan MD, Swanson DD, Glass RS, Wilson GS (1981) J Phys Chem 85:1069–1075
Brown TG, Hirschon AS, Musker WK (1981) J Phys Chem 85:3767–3771
Evans DH, Gruhn NE, Jin J, Li B, Lorance E, Okumura N, Macias-Ruvalcaba NA, Zakai UI, Zhang S-Z, Block E, Glass RS (2010) J Org Chem 75:1997–2009
Deng Y, Illies AJ, James MA, McKee ML, Peschke M (1995) J Am Chem Soc 117:420–428
de Visser SP, de Konning LJ, Nibbering NMM (1996) Int J Mass Spectrum Ion Process 157/158:283–291
James MA, Illies AJ (1996) J Phys Chem 100:15794–15799
Furukawa N, Kawada A, Kawai T (1984). J Chem Soc Chem Commun: 1151–1152
Fujihara H, Akaishi R, Furukawa N (1987) J Org Chem 52:4254–4257
Fujihara H, Akaishi R, Furukawa N (1987) J Chem Soc Chem Commun: 930–931
Fujihara H, Furukawa N (1989) J Mol Struct THEOCHEM 55:261–272
Iwasaki F, Toyoda N, Akaishi R, Fujihara H, Furukawa N (1988) Bull Chem Soc Jpn 61:2563–2567
Fujihara H, Akaishi R, Nakamura A, Furukawa N (1990) Tetrahedron Lett 31:6375–6378
Fujihara H, Akaishi R, Erata T, Furukawa N (1989). Chem Commum: 1789–1790
Fujihara H, Akaishi R, Furukawa N (1993) Tetrahedron 49:1605–1618
Iwasaki F, Morimoto M, Yasui M, Akaishi R, Fujihara H, Furukawa N (1991) Acta Crystallogr C47:1463–1466
Fujihara H, Furukawa N (1992) Phosphorus Sulfur Silicon Relat Elem 67:131–134
Fujihara H, Yabe M, Chiu J-J, Furukawa N (1991) Tetrahedron Lett 32:4345–4348
Fujihara H, Ninoi T, Akaishi R, Erata T, Furukawa N (1991) Tetrahedron Lett 32:4537–4540
Fujihara H, Ninoi T, Akaishi R, Erata T, Furukawa N (1991) Tetrahedron Lett 32:4537–4540; footnote 4
Block E, Dikarev EV, Glass RS, Jin J, Li B, Li X, Zhang S-Z (2006) J Am Chem Soc 128:14949–14961
Fujihara H, Mima H, Chiu J-J, Furukawa N (1990) Tetrahedron Lett 31:2307–2310
Fujihara H, Takaguchi Y, Chiu J-J, Erata T, Furukawa N (1992) Chem Lett 21:151–154
Takaguchi Y, Fujihara H, Furukawa N (1996) Organometallics 15:1913–1919
Nakanishi W, Hayashi S, Toyota S (1998) J Org Chem 63:8790–8800
Hayashi S, Nakanishi W (1999) J Org Chem 64:6688–6696
Nakanishi W, Hayashi S, Morinaka S, Sasamori T, Tokitoh N (2008) New J Chem 32:1881–1889
Nakayama N, Takahashi O, Kikuchi O, Furukawa N (2000) Heteroatom Chem 11:31–41
Brundle CR, Baker A (1977) Electron spectroscopy: theory techniques, and applications, vol 1. Academic, London
Rabalais JW (1977) Principles of ultraviolet photoelectron spectroscopy. Wiley, New York
Ghosh PK (1983) Introduction to photoelectron spectroscopy. Wiley, New York
Barr TL (1994) Modern ESCA. The principles and practice of x-ray photoelectron spectroscopy. CRC Press, Boca Raton
Koopmans T (1933) Physica 1:104–113
Glass RS, Broeker JL, Jatcko ME (1989) Tetrahedron 45:1263–1272
Nadjo L, Savéant JM (1973) Electroanal Chem Interfac Electrochem 48:113–145
Houmam A (2008) Chem Rev 108:2180–2237
Hoffmann R (1971) Acc Chem Res 4:1–9
Gleiter R (1974) Angew Chem Int Ed 13:696–701
Brunck TK, Weinhold F (1976) J Am Chem Soc 98:4392–4393
Setzer WN, Glass RS (1988) In: Glass RS (ed) Conformational analysis of medium-sized heterocycles. Verlag Chemie, Weinheim
Drouin BJ, Madden JF, Gruhn NE, Kukolich SG, Barfield M, Glass RS (1997) J Phys Chem A 101:9180–9184
Glass RS, Block E, Gruhn NE, Jin J, Lorance E, Zakai UI, Zhang S-Z (2007) J Org Chem 72:8290–8297
Block E, Glass RS, Gruhn N, Jin J, Lorance E, Zakai UI, Zhang S-Z (2008) Phosphorus Sulfur Silicon 183:856–862
Glass RS, Radspinner AM, Singh WP (1992) J Am Chem Soc 114:4921–4923
Glass RS, Guo Q, Liu Y (1997) Tetrahedron 53:12273–12286
Li H, Nishiwaki K, Itami K, Yoshida J (2001) Bull Chem Soc Jpn 74:1717–1725
Yoshida J, Maekawa T, Murata T, Matsunaga S, Isoe S (1990) J Am Chem Soc 112:1962–1970
Block E, Yencha AJ, Aslam M, Eswarakrishnan V, Lao J, Sano J (1988) J Am Chem Soc 110:4748–4753
Block E, Aslam M (1988) Tetrahedron 44:281–324
Block E, Glass RS, Dikarev EV, Gruhn NE, Jin J, Li B, Lorance E, Zakai UI, Zhang S-Z (2007) Heteroatom Chem 18:509–515
Glass RS, Block E, Lorance E, Zakai UI, Gruhn NE, Jin J, Zhang S-Z (2006) J Am Chem Soc 128:12685–12692
Werst DW, Trifunac AD (1991) J Phys Chem 95:3466–3477
Werst DW (1991) J Am Chem Soc 113:4345–4346
Werst DW (1992) J Phys Chem 96:3640–3646
Morgan RS, Tabsch CE, Gushard RH, McAdon JM, Warme PK (1978) Int J Peptide Protein Res 11:209–217
Breinlinger EC, Keenan CJ, Rotello VM (1998) J Am Chem Soc 120:8608–8609
Rotello VM (1998) Heteroatom Chem 9:605–606
Low DW, Hill MG (1998) J Am Chem Soc 120:11536–11537
Butterfield DA (2002) Free Radic Res 36:1307–1313
Butterfield DA, Kanski J (2002) Peptides 23:1299–1309
Butterfield DA (2003) Curr Med Chem 10:2651–2659
Schöneich C (2005) Biochim Biophys Acta 1703:111–119
Huang X, Atwood CS, Hartshorn MA, Multhap G, Goldstein LE, Scarpa RC, Cuajungco MP, Gray DN, Lim J, Moir RD, Tanzi RE, Bush AI (1999) Biochemistry 38:7609–7616
Huang X, Cuajungco MP, Atwood CS, Hartshorn MA, Tyndall JDA, Hanson GR, Stokes KC, Leopold M, Multhaup G, Goldstein LE, Scarpa RC, Saunders AJ, Lim J, Moir RD, Glabe C, Bowden EF, Masters CL, Fairlie DP, Tanzi RE, Bush AI (1999) J Biol Chem 274:37111–37116
Opuzo C, Huang X, Cherny RA, Moir RD, Roher AE, White AR, Cappai R, Masters EL, Tanzi RE, Inestrosa NC, Bush AI (2002) J Biol Chem 277:40302–40308
Del Rio MJ, Velez-Pardo C (2004) Curr Med Chem Cent Nerv Syst Agents 4:279–285
Petkova AT, Ishii Y, Bulbach JJ, Antzutkin ON, Leapman RD, Delaglio F, Tycko R (2002) Proc Natl Acad Sci USA 99:16742–16747
Petkova AT, Yau W-M, Tycko R (2006) Biochemistry 45:498–512
Miller Y, Ma B, Nussinov R (2010) Chem Rev 110:4820–4839
Luhrs T, Ritter C, Adrian M, Riek-Loher D, Bohrman B, Döbeli H, Schubert D, Riek R (2005) Proc Natl Acad Sci USA 102:17342–17347
Ma B, Nussinov R (2006) Curr Opin Chem Biol 10:445–452
Horn AHC, Sticht H (2010) J Phys Chem B 114:2219–2226
Chung WJ, Ammam M, Gruhn NE, Nichol GS, Singh WP, Wilson GS, Glass RS (2009) Org Lett 11:397–400
Coleman BR, Glass RS, Setzer WN, Prabhu UDG, Wilson GS (1982) Adv Chem Ser 201:417–441
Zakai UI, Bloch-Mechkour A, Jacobsen NE, Abrell L, Lin G, Nichol GS, Bally T, Glass RS (2010) J Org Chem 75:8363–8371
Ammam M, Zakai UI, Wilson GS, Glass RS (2010) Pure Appl Chem 82:555–563
Elinson MN, Simonet J, Toupet L (1993) J Electroanal Chem 350:117–132
Jones IW, Tebby JC (1979) J Chem Soc Perkin Trans 2:217–218
Emsley JW, Longeri M, Veracini CA, Catalano D, Pedulli GF (1982) J Chem Soc Perkin Trans 2:1289–1296
Vondrak T, Sato S, Spirko V, Kimura K (1997) J Phys Chem A 101:8631–8638
Frolov YuL, Vashchenko AV (2003) Russ J Org Chem 39:1412–1414
Baciocchi E, Gerini MF (2004) J Phys Chem A 108:2332–2338
Dewar PS, Ernstbrunner E, Gilmore JR, Godfrey M, Mellor JM (1974) Tetrahedron 30:2455–2459
Schweig A, Thon N (1976) Chem Phys Lett 38:482–485
Colle MD, Distefano G, Jones D, Modelli A (2000) J Phys Chem A 104:8227–8233
Bossa M, Morpurgo S, Stranges S (2002) J Mol Struct THEOCHEM 618:155–164
Jouikov V (1995) J Electroanal Chem 398:159–164
Jouikov V, Ivkor V (1995) Electrochim Acta 40:1617–1622
Tschmutowa G, Block H (1976) Z Naturforsch B 31:1611–1615
Baker AD, Armen GH, Guang-di Y (1981) J Org Chem 46:4127–4130
Bzheovskii VM, Kapustin EG (2003) Russ J Gen Chem 73:54–60
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Glass, R.S. (2011). Redox Chemistry of Sulfur, Selenium and Tellurium Compounds. In: Woollins, J., Laitinen, R. (eds) Selenium and Tellurium Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-20699-3_3
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