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Solute-Solvent Interaction Effects on Protonation Equilibrium of Substituted N-Benzylidene-2-hydroxyanilines in Aqueous Ethanol: The Application of Factor Analysis to Solvatochromic Parameters and Protonation Equilibria

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Summary.

In this study, the stoichiometric protonation constants, logK OH and logK NH, of sixteen substituted N-benzylidene-2-hydroxyanilines have been determined potentiometrically in ethanol-water mixtures of varying composition (10–80% ethanol by volume) at 25.0±0.1°C. The values of the constants, logK, were submitted to factor analysis in order to obtain the number of factors which affect the variation of the whole data sets of protonation constants and, afterwards, to target factor analysis to identify these factors. The influence of solvatochromic parameters in the interactions between Schiff bases derivatives and the solvent studied was identified and quantified. Kamlet and Taft general equations allow calculation of the logK values of Schiff bases studied in any ethanol-water mixtures up to 80% (v/v) and thus provide the knowledge of the acid-base behaviour in these solvent media. Further, the quasi-lattice quasi-chemical (QLQC) theory of preferential solvation has been applied to quantify the preferential solvation by water of electrolytes in ethanol-water mixtures.

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References

  • Z Cimerman N Galic B Bosner (1997) Anal Chim Acta 343 145 Occurrence Handle1:CAS:528:DyaK2sXis1Wnu7w%3D Occurrence Handle10.1016/S0003-2670(96)00587-9

    Article  CAS  Google Scholar 

  • VD Athawale SS Nerkar (2000) Monatsh Chem 131 267 Occurrence Handle1:CAS:528:DC%2BD3cXivFGnsb4%3D Occurrence Handle10.1007/s007060070102

    Article  CAS  Google Scholar 

  • Dürr H, Bouas-Laurent H (1990) Photochromism Molecules and Systems eds, Elsevier, Amsterdam, Chapter 17

  • a) Kawato T, Koyama H, Kanatomi H, Isshiki M (1985) J Photochem 28: 103; b) Kawato T, Kanatomi H, Koyama H, Igarashi T (1986) J Photochem 33: 199

  • Cohen MD, Schmidt MJ, Flavin S (1964) J Chem Soc 2041

  • a) Hadjoudis E, Milia F, Seliger J, Blinc R, Zagar V (1980) Chem Phys 47: 105; b) Inabe T, Gautier-Luneau S, Hoshino N, Okaniwa K, Okamoto H, Mitani T, Nagashima U, Maruyama Y (1991) Bull Chem Soc Jpn 64: 801; c) Inabe T, Luneau I, Mitani T, Maruyama Y, Takeda S (1994) Bull Chem Soc Jpn 67: 612; d) Sekikawa T, Kobayashi T, Inabe T (1997) J Phys Chem A 101: 644; e) Pizzala H, Carles M, Stone WEE, Thevand A (2000) J Chem Soc Perkin 2: 935

  • D Gegiou E Lambi E Hadjoudis (1996) J Phys Chem 100 17762 Occurrence Handle1:CAS:528:DyaK28Xmt1Ggtbc%3D Occurrence Handle10.1021/jp961115l

    Article  CAS  Google Scholar 

  • I Shehatta (2002) Helv Chim Acta 85 2125 Occurrence Handle1:CAS:528:DC%2BD38Xmt1Oqtrw%3D Occurrence Handle10.1002/1522-2675(200207)85:7<2125::AID-HLCA2125>3.0.CO;2-U

    Article  CAS  Google Scholar 

  • J Barbosa G Fonrodona I Marqués S Butí I Toro (1997) Trends Anal Chem 16 104 Occurrence Handle1:CAS:528:DyaK2sXhvVGksLw%3D Occurrence Handle10.1016/S0165-9936(96)00101-X

    Article  CAS  Google Scholar 

  • C Reichardt (1994) Chem Rev 94 2319 Occurrence Handle1:CAS:528:DyaK2cXntV2gtrY%3D Occurrence Handle10.1021/cr00032a005

    Article  CAS  Google Scholar 

  • E Casassas G Fonrodona A De Juan (1992) J Solution Chem 21 147 Occurrence Handle1:CAS:528:DyaK38Xhslent7g%3D Occurrence Handle10.1007/BF00647004

    Article  CAS  Google Scholar 

  • C Reichardt (1990) Solvents and Solvent Effects in Organic Chemistry EditionNumber2 VCH Weinheim

    Google Scholar 

  • H Langhals (1982) Angew Chem Int Ed Engl 21 724 Occurrence Handle10.1002/anie.198207241

    Article  Google Scholar 

  • Marcus Y (2002) Solvent Mixtures Properties and Selective Solvation Marcell Dekker, Inc., New York, Basel

  • DC Silva I Ricken MAR Silva VG Machado (2002) J Phys Org Chem 15 420 Occurrence Handle10.1002/poc.519 Occurrence Handle1:CAS:528:DC%2BD38XltF2is74%3D

    Article  CAS  Google Scholar 

  • MS Mayadeo SS Purohit (1980) J Indian Chem Soc 57 265 Occurrence Handle1:CAS:528:DyaL3cXltVaiurs%3D

    CAS  Google Scholar 

  • U Doraswamy PK Bhattacharya (1984) J Indian Chem Soc 15A 253

    Google Scholar 

  • Y Altun (2004) J Solution Chem 33 479 Occurrence Handle1:CAS:528:DC%2BD2cXms1Cgurs%3D Occurrence Handle10.1023/B:JOSL.0000037772.55748.a3

    Article  CAS  Google Scholar 

  • Altun Y (2005) Monatsh Chem (in Press)

  • K Hagemark (1968) J Phys Chem 72 2316 Occurrence Handle1:CAS:528:DyaF1cXksVKmsbc%3D Occurrence Handle10.1021/j100853a006

    Article  CAS  Google Scholar 

  • Y Marcus (1988) J Chem Soc Faraday Trans I 84 1465 Occurrence Handle1:CAS:528:DyaL1cXhslCmtLc%3D Occurrence Handle10.1039/f19888401465

    Article  CAS  Google Scholar 

  • Y Marcus Y Migron (1994) Phys Chem 95 400

    Google Scholar 

  • J Barbosa V Sanz-Nebot (1994) J Chem Soc Faraday Trans 90 3287 Occurrence Handle1:CAS:528:DyaK2MXitVehs74%3D Occurrence Handle10.1039/ft9949003287

    Article  CAS  Google Scholar 

  • MJ Kamlet RW Taft (1976) J Am Chem Soc 98 377 Occurrence Handle1:CAS:528:DyaE28XovFeqtA%3D%3D Occurrence Handle10.1021/ja00418a009

    Article  CAS  Google Scholar 

  • MJ Kamlet JL Abboud RW Taft (1976) J Am Chem Soc 99 6027 Occurrence Handle10.1021/ja00460a031

    Article  Google Scholar 

  • MJ Kamlet JL Abboud MH Abraham RW Taft (1983) J Org Chem 48 2877 Occurrence Handle1:CAS:528:DyaL3sXkvVOgsbc%3D Occurrence Handle10.1021/jo00165a018

    Article  CAS  Google Scholar 

  • T Gündüz E Kılıç E Canel F Köseoğlu (1993) Anal Chim Acta 282 489 Occurrence Handle10.1016/0003-2670(93)80112-X

    Article  Google Scholar 

  • F Köseoğlu E Kılıç E Canel N Yılmaz (1994) Anal Chim Acta 293 87 Occurrence Handle10.1016/0003-2670(94)00077-8

    Article  Google Scholar 

  • GM Badger (1954) The Structure and Reactions of Aromatic Compounds Cambridge University Press UK 202

    Google Scholar 

  • RT Morrison RN Boyd (1990) Organic Chemistry EditionNumber5 Prentice Hall New Delhi 203

    Google Scholar 

  • Sollenberger PY, Martin RB (1968) The Chemistry of Amino Group, Chapter 7 by edited S. Patai John Wiley & Sons, London

  • P Nagy (1989) J Mol Struct 201 271 Occurrence Handle10.1016/0166-1280(89)87081-2

    Article  Google Scholar 

  • DL Ross CM Riley (1992) Int J Pharm 83 267 Occurrence Handle1:CAS:528:DyaK38Xlt1Cjs7Y%3D Occurrence Handle10.1016/0378-5173(82)90032-1

    Article  CAS  Google Scholar 

  • J Barbosa R Bergés I Toro V Sanz-Nebot (1997) Talanta 44 1271 Occurrence Handle1:CAS:528:DyaK2sXktVWhu74%3D Occurrence Handle10.1016/S0039-9140(96)02188-1

    Article  CAS  Google Scholar 

  • RG Bates (1973) Determination of pH, Theory and Practice EditionNumber2 Wiley New York

    Google Scholar 

  • GH Parsons CH Rochester (1975) J Chem Soc Faraday Trans I 75 1058 Occurrence Handle10.1039/f19757101058

    Article  Google Scholar 

  • M Roses C Rafols J Ortega E Bosch (1995) J Chem Soc, Perkin Trans 2 1607

    Google Scholar 

  • Y Marcus (2001) Monatsh Chem 132 1387 Occurrence Handle1:CAS:528:DC%2BD3MXptVamu74%3D

    CAS  Google Scholar 

  • YG Wu M Tabata T Takamuku (2002) J Solution Chem 31 381 Occurrence Handle1:CAS:528:DC%2BD38Xksl2lur4%3D Occurrence Handle10.1023/A:1015859315320

    Article  CAS  Google Scholar 

  • A Ben-Naim (1990) Pure & Apll Chem 62 25 Occurrence Handle1:CAS:528:DyaK3cXhtVKiu78%3D

    CAS  Google Scholar 

  • RG Bates (1971) J Electroanal Chem 29 6 Occurrence Handle10.1016/0368-1874(71)85121-3

    Article  Google Scholar 

  • England BD, House DA (1962) J Chem Soc 4421

  • MJ Kamlet JF Gal PC Maria RW Taft (1985) J Chem Soc Perkin Trans 2 1583

    Google Scholar 

  • B Hemmateenejad H Sharghi M Akhond M Shamsipur (2003) J Solution Chem 32 215 Occurrence Handle1:CAS:528:DC%2BD3sXisVGgsr4%3D Occurrence Handle10.1023/A:1022982200712

    Article  CAS  Google Scholar 

  • E Pfeiffer E Breith E Lubbe T Tsumaki (1993) Justus Liebigs Ann Chem 503 84

    Google Scholar 

  • G Gran (1952) Analyst 7 661 Occurrence Handle10.1039/an9527700661

    Article  Google Scholar 

  • AE Martell RJ Motekaitis (1988) The Determination and Use of Stability Constants VCH Weinheim

    Google Scholar 

  • ER Malinowski (2002) Factor Analysis in Chemistry EditionNumber3 John Wiley & Sons New York

    Google Scholar 

  • A Gustavo González D González-Arjona (1995) Anal Chim Acta 312 295 Occurrence Handle10.1016/0003-2670(95)00225-O

    Article  Google Scholar 

  • D Gonzáles-Arjona J Antonio Mejías A Gustavo González (1994) Anal Chim Acta 295 119 Occurrence Handle10.1016/0003-2670(94)80341-2

    Article  Google Scholar 

  • D Gonzáles-Arjona J Antonio Mejías A Gustavo González (1994) Anal Chim Acta 297 473 Occurrence Handle10.1016/0003-2670(94)00437-4

    Article  Google Scholar 

  • MATLAB, The Math Works, Inc., Natick, MA

  • RI Shager (1986) Chemometr Intell Lab Syst 1 59 Occurrence Handle10.1016/0169-7439(86)80026-0

    Article  Google Scholar 

  • U Buhvestov F Rived C Ráfols E Bosch M Roses (1998) J Phys Org Chem 11 185 Occurrence Handle1:CAS:528:DyaK1cXisFSgs74%3D Occurrence Handle10.1002/(SICI)1099-1395(199803)11:3<185::AID-POC993>3.0.CO;2-5

    Article  CAS  Google Scholar 

  • JH Park MD Jang DS Kim PW Carr (1990) J Chrom 513 107 Occurrence Handle1:CAS:528:DyaK3cXltl2gsLc%3D Occurrence Handle10.1016/S0021-9673(01)89429-2

    Article  CAS  Google Scholar 

  • M El-Sayed H Müller G Rheinwald H Lang S Spange (2003) Monatsh Chem 134 361 Occurrence Handle1:CAS:528:DC%2BD3sXht1KhsL8%3D

    CAS  Google Scholar 

Download references

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  1. Department of Chemistry, Faculty of Gazi Education, Gazi University, Ankara, Turkey

    Yüksel Altun & Fitnat Köseoğlu

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  1. Yüksel Altun
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  2. Fitnat Köseoğlu
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Correspondence to Yüksel Altun.

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Altun, Y., Köseoğlu, F. Solute-Solvent Interaction Effects on Protonation Equilibrium of Substituted N-Benzylidene-2-hydroxyanilines in Aqueous Ethanol: The Application of Factor Analysis to Solvatochromic Parameters and Protonation Equilibria. Monatsh. Chem. 137, 703–716 (2006). https://doi.org/10.1007/s00706-005-0477-6

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