Abstract
The oxidative and reductive electrochemistry of the three isomeric nitroanilines has been studied in neutral (0.1 mol L−1 KClO4) and acidic (0.1 mol L−1 HClO4) aqueous electrolyte solutions by cyclic voltammetry and surface enhanced Raman spectroscopy (SERS). The cyclic voltammograms recorded for o- and p-nitroanilines with a gold electrode in acidic solution, scanning toward negative potentials, revealed formation of phenylenediamine not observed in neutral solution. Similar behavior of nitroanilines and phenylenediamines was observed on gold and platinum electrodes. An oxygen–gold adsorbate stretching mode was detected between 400 and 430 cm−1 in the SER-spectra of the three isomeric nitroanilines in both electrolyte solutions at positive electrode potentials, implying perpendicular adsorption via the nitro group.
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Nobutoki H, Koezuka H (1997) J Phys Chem 101:3762
Bertinelli F, Palmieri P, Brillante A, Taliani C (1977) Chem Phys 25:333
Stähelin M, Burland DM, Rice JE (1992) Chem Phys Lett 191:245
Woodford JN, Pauley MA, Wang CH (1997) J Phys Chem A 101:1989
Huyskens FL, Huyskens PL, Persoons AP (1998) J Chem Phys 108:8161
Turi L, Dannenberg JJ (1996) J Phys Chem 100:9638
Szostak MM, Kozankiewicz B, Wojcik G, Lipinski J (1998) J Chem Soc Faraday Trans 94:3241
Hurst M, Munn RW (1989) Special publication, Royal Society of Chemistry (Org Mater non-linear Opt) 69:3
Hutter J, Wagniere G (1988) J Mol Struct 175:159
Dannenberg JJ (1991) ACS Symp Ser (Mater Nonlinear Opt) 455:457
Wesch A, Dannenberger O, Wöll C, Wolff JJ, Buck M (1996) Langmuir 12:5330
Schmid ED, Moschallski M, Peticolas WL (1986) J Phys Chem 90:2340
Kumar K, Carey PR (1975) J Phys Chem 63:3697
Schmidt PH, Plieth WJ (1986) J Electroanal Chem 201:163
Holze R, Surface and interface analysis: an electrochemists toolbox, Springer, Berlin Heidelberg New York, in preparation
Holze R (1991) Electrochim Acta 36:1523
Gao P, Weaver MJ (1985) J Phys Chem 89:5040
Li YS, Lin X, Cao YH (1999) Vib Spectrosc 20:95
Li Y-S, Vo-Dinh T, Stokes DL, Wang Y (1992) Appl Spectrosc 46:1354
Hu J, Zhao B, Xu W, Fan Y, Li B, Ozaki Y (2002) J Phys Chem B 106:6500
Hu J, Zhao B, Xu W, Fan Y, Li B, Ozaki Y (2002) Langmuir 18:6839
Roth I, Jbarah AA, Spange S, Holze R, work in progress
Astle MJ, McConnell WV (1943) J Am Chem Soc 65:35
Ravichandran C, Vasudevan D, Anantharaman PN (1992) J Appl Electrochem 22:1192
Jagganathan E, Mohamed M, Ahmed KAB, Anantharaman PN (1988) J Electrochem Soc India 37:65
Jagannathan E, Chellammal S, Tirunavukkarasu P, Anantharaman PN (1990) Trans SAEST 25:25
Holze R (1988) Surf Sci 202:L612
Holze R (1990) Electrochim Acta 35:1037
Karpiński ZJ, Kublik Z (1986) Pol J Chem 68:269
Testa AC, Reinmuth WH (1961) J Am Chem Soc 83:784
Stradins J, Kravis I (1975) J Electroanal Chem 65:635
Bencheikh-Sayarh S, Pouillen P, Martre A-M, Martinet P (1983) Electrochim Acta 28:627
Bencheikh-Sayarh S, Cheminat B, Mousset G, Pouillen P (1984) Electrochim Acta 29:1225
Mohammad M, Khan AY, Afzal M, Niza A, Ahmed R (1974) Aust J Chem 27:2495
Geske DH, Ragle JI, Bambenek MA, Balch AI (1964) J Am Chem Soc 86:987
Allendoerfer RD, Rieger PH (1966) J Am Chem Soc 88:3711
Runner ME (1952) J Am Chem Soc 74:3567
Shreve OD, Markham EC (1949) J Am Chem Soc 71:2993
Parkash R, Kalla RK, Verma RS (1976) Proc Indian Acad Sci 84A:64
Carastoian AI, Banica FG, Moraru M (1993 ) Rev Roum Chim 38:287; Carastoian AI, Banica FG, Moraru M (1993 ) 38:615
Tomat R (1970) Chimica e L’Industria 52:438
Ana MAS, Chadwick I, Gonzalez G (1982) Bol Soc Chil Quim 27:244
Ana MAS, Chadwick I, Gonzalez G (1985) J Chem Soc Perkin Trans II 1755
Wawzonek S, Mclntire TW (1967) J Electrochem Soc 114:1025
Shenglong W, Fosong W, Xiaohui G (1986) Synth Met 16:99
Heineman WR, Wieck HJ, Yacynych AM (1980) Anal Chem 52:345
Malitesta C, Palmizano F, Torsi L, Zambonin PG (1990) Anal Chem 62:2735
Ye B-X, Zhang W-M, Zhou X-Y (1997) Chin J Chem 15:343
Xu J, Sun X, Liu B, Xu F (2001) Anal Sci 17:i1363
Piette LH, Ludwig P, Adams RN (1962) Anal Chem 34:916
Kitani A, So Y-H, Miller LL (1981) J Am Chem Soc 103:7636
Kitani A, Miller LL (1981) J Am Chem Soc 103:3595
Ravichandran K, Baldwin RP (1983) Anal Chem 55:1586
Duca A, Bejan D (1991) Rev Roum Chim 36:439
Stočesová D (1949) Collect Czech Chem Commun 14:615
Yang L, Guang-Zhi X, Jing-Gui S, Jin-Liang G, You-Qi T (1989) Acta Chim Sin (Eng Ed) 4:365
Genies EM, Lapkowski M (1987) J Electroanal Chem 236:189
Bacon J, Adams RN (1968) J Am Chem Soc 90:6596
Roy BC, Gupta MD, Ray JK (1995) Macromolecules 28:1727
Koval’chuk EP, Whittingham S, Skolozdra OM, Zavalij PY, Zavaliy IY, Reshetnyak OV, Seledets M (2001) Mater Chem Phys 69:154; Koval’chuk EP, Whittingham S, Skolozdra OM, Zavalij PY, Zavaliy IY, Reshetnyak OV, Blazejowski J (2001) Mater Chem Phys 70:38
Varsányi G (1974) Assignments for vibrational spectra of seven hundred benzene derivatives. Adam Hilger, London
Dollish FR, Fateley WG, Bentley FF (1974) Characteristic Raman frequencies of organic compounds. Wiley, New York
Muniz-Miranda M (1997) J Raman Spectrosc 28:205
Gao X, Davies JP, Weaver MJ (1990) J Phys Chem 94:6858
Tanaka T, Nakajima A, Watanabe A, Ohno T, Ozaki Y (2003) J Mol Struct 661/662:437
Holze R (1987) Electrochim Acta 32:1527
Holze R (1988) J Electroanal Chem 250:143
Vaschetto ME, Retamal BA, Monkman AP (1999) J Mol Struct 468:209
Szostak MM (1979) J Raman Spectrosc 8:43
Boggetti H, Anunziata JD, Cattana R, Silber JJ (1994) Spectrochim Acta, 50A:719
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Financial support from the Fonds der Chemischen Industrie and the Deutsche Forschungsgemeinschaft is gratefully acknowledged.
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Jbarah, A.A., Holze, R. A comparative spectroelectrochemical study of the redox electrochemistry of nitroanilines. J Solid State Electrochem 10, 360–372 (2006). https://doi.org/10.1007/s10008-005-0686-2
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DOI: https://doi.org/10.1007/s10008-005-0686-2