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Journal of the Serbian Chemical Society, Vol. 74, 2009, No. 12 JSCSEN 749 (12 ) 1335 1516– (200 ) v eersion lectronic VOLUME 74 Available on line at No 12 BELGRADE 2009 www.shd.org.rs/JSCS/ The full search of JSCS is available through www.doaj.org J. Serb. Chem. Soc. Vol. 74, No. 12 (2009) CONTENTS G. S. Ušćumlić and J. B. Nikolić: The study of linear solvation energy relationship for the reactivity of ca rboxylic acids with diazodiphenylmethane in protic and aprotic sol- vents (Authors’ Review) ............................................................................................. 1335 Organic Chemistry S. Ž. Drmanić, A. D. Marinković and B. Ž. Jovanović: Effects of solvent and structure on the reactivity of 6-substituted nicotinic acids with diazodiphenylmethane in aprotic solvents ....................................................................................................................... 1359 B. Maleki, D. Azarifar, M. K. Moghaddam, S. F. Hojati, M. Gholizadeh and H. Salehabadi: Synthesis and characterization of a series of 1,3,5-trisubstituted-2-pyrazolines deri- vatives using methanoic acid under thermal condition (Short communication) .......... 1371 Biochemistry and Biotechnology M. A. Rode, S. S. Rindhe and B. K. Karale: Synthesis and biological activities of some indoline derivatives ..................................................................................................... 1377 Q. Kanwal, I. Hussain, H. L. Siddiqui and A. Javaid: Flavonoids from mango leaves with antibacterial activity .................................................................................................... 1389 Inorganic Chemistry M. Zdujić, D. Poleti, Č. Jovalekić and Lj. Karanović: Mec hanochemical synthesis and δ electrical conductivity of nanocrystalline -Bi2O3 stabilized by HfO2 and ZrO2 ....... 1401 S. Chandra and A. Gautam: Spectroscopic and biological a pproach in the c haracteriza- tion of Cr(III), Mn(II) and Co(II) com plexes with a novel hexaazam acrocyclic li- gand derived from semicarbazide ............................................................................... 1413 Theoretical Chemistry T.-C. Lim: Obt aining the Varshni potential fu nction u sing th e 2-body Kaxir as–Pandey parameters ................................................................................................................... 1423 Physical Chemistry A. Zarubica, B. Jović, A. Nikolić, P. Putanov and G. Bošković: Te mperature i mposed textural and surface synergism affecting the isomerization activity of sulfated zirco- nia catalysts ................................................................................................................. 1429 Electrochemistry H. Yaghoubian, H. Karimi-Maleh, M. A. Khalilzadeh and F. Karimi: Electrochemical de- tection of carbidopa using a ferrocene-modified carbon nanotube paste electrode ..... 1443 Analytical Chemistry V. J. Guzsvány, Z. J. Papp, S. D. Lazić, F. F. Gaál, L. J. Bjelica and B. F. Abramović: A rapid spectro photometric det ermination of im idacloprid in select ed co mmercial formulations in the presence of 6-chloronicotinic acid ............................................... 1455 W. Zhang, X. Niu, N. Zhao and W. Sun: Sensitive voltammetric detection of y east RNA based on its interaction with Victoria Blue B .............................................................. 1467 Geochemistry P. I. Premović, J. Ciesielczuk, B. Ž. Todorović, D. M. Djordjević and N. S. Krstić: Geo- chemistry of F e3+ in the hy drothermal di ckite fro m Jedlina Zdroj (Lower Silesia, Poland) ........................................................................................................................ 1477 Contents of Volume 74 ....................................................................................................... 1491 Subject index ....................................................................................................................... 1503 Author index ....................................................................................................................... 1511 Published by the Serbian Chemical Society Karnegijeva 4/III, 11000 Belgrade, Serbia Printed by the Faculty of Technology and Metallurgy Karnegijeva 4, P.O. Box 35-03, 11120 Belgrade, Serbia Available online at www.shd.org.rs/JSCS/ ___________________________________________________________________________________________________________________________ 2009 Copyright (CC) SCS J. Serb. Chem. Soc. 74 (12) 1335–1357 (2009) UDC 547–32:547.437’631: JSCS–3922 544–145.55:541.42 Authors’ Review AUTHORS’ REVIEW The study of linear solvation energy relationship for the reactivity of carboxylic acids with diazodiphenylmethane in protic and aprotic solvents GORDANA S. UŠĆUMLIĆ*# and JASMINA B. NIKOLIĆ# Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, P.O. Box 3505, 11120 Belgrade, Serbia (Received 15 June 2009) Abstract: Solvent effects on the reactivity of cycloalkenecarboxylic, cycloalke- neacetic, 2-substituted cyclohex-1-enecarboxylic, 2-substituted benzoic, 2-sub- stituted cyclohex-1-eneacetic, 2-substituted phenylacetic, 2-phenylcyclohex-1- enecarboxylic, 2-phenylbenzoic and 2-phenylacrylic acids with diazodiphe- nylmethane (DDM) were investigated. In order to explain the kinetic results through solvent effects, the second-order rate constants for the reaction of the examined acids with DDM were correlated using the Kamlet–Taft solvato- chromic equation. The correlations of the kinetic data were realized by means of multiple linear regression analysis and the solvent effects on the reaction rates were analyzed in terms of the contributions of the initial and the transition state. The signs of the equation coefficients support the proposed mechanism. Solvation models for all the investigated acids are suggested. The quantitative relationship between the molecular structure and the chemical reactivity is also discussed. Keywords: carboxylic acids; linear solvation energy relationship; diazodiphe- nylmethane; aprotic solvents; protic solvents. CONTENTS 1. INTRODUCTION 2. HYDROXYLIC SOLVENT EFFECTS ON THE KINETICS OF THE REACTION OF CARBOXYLIC ACIDS WITH DIAZODIPHENYLMETHANE 3. THE KAMLET–TAFT METHOD FOR THE EXAMINATION OF SOLVENT EFFECTS ON THE REACTIVITY OF CARBOXYLIC ACIDS WITH DIAZODIPHENYLMETHANE 3.1. Cycloalkenecarboxylic and cycloalkeneacetic acids 3.2. 2-Substituted cyclohex-1-enecarboxylic and 2-substituted benzoic acids 3.3. 2-Substituted cyclohex-1-eneacetic and 2-substituted phenylacetic acids 3.4. 2-Phenylcyclohex-1-enecarboxylic, 2-phenylbenzoic and 2-phenylacrylic acids 4. CONCLUDING REMARKS * Corresponding author. E-mail: [email protected] # Serbian Chemical Society member. doi: 10.2298/JSC0912335U 1335 Available online at www.shd.org.rs/JSCS/ ___________________________________________________________________________________________________________________________ 2009 Copyright (CC) SCS 1336 UŠĆUMLIĆ and NIKOLIĆ 1. INTRODUCTION The effect of different solvents on the rates of chemical changes was one of the earliest kinetic problems to be studied.1–3 The development of correlation analysis in the area of solvent effects has proved to be a slow and difficult pro- cess and only within the last 20 years has there been any considerable progress. Application of the techniques of multiple regression has proved to be strikingly successful and has greatly increased the understanding of the role of the solvent. Over the years, two main methods for the examination of the solvent effects on the reaction rates have been developed. First, the rate constants, either as log k or as ΔG# may be correlated with a physical parameter characteristic of the solvent, for example dielectric constant, solubility parameter, viscosity, etc., or with an empirical solvent parameter, such as Y, Z, etc.4–6 This type of analysis has been extended to multiple linear correlations with a number of solvent parameters, notably by Shorter et al.7 on the reaction of diazodiphenylmethane (DDM) and benzoic acid and more generally by Koppel and Palm8 and by Kamlet and Taft and their co-workers.9–11 In the second method, the solvent effect on log k or ΔG# is dissected into contributions of the reactants (initial state) and the tran- sition state, followed, where possible, by a comparison of solvent effects on the transition state with solvent effects on solutes that might function as suitable models for the transition state. This method has been applied not only to a num- ber of standard organic reactions but also to organometallic and inorganic reactions. Two groups of workers set out general equations for the correlations of sol- vent effects through multiple regression analysis. Koppel and Palm8 used the four-parameter Eq. (1): log k = log k0 + gf(ε) + pf(n) + eE + bB (1) in which f(ε) is a dielectric constant function, usually Q = (ε – 1)/(2ε +1), f(n) is a refractive index function, (n2 – 1)/(n2 + 2), and E and B are measures of the electrophilic and nucleophilic solvation ability of the solvent, respectively. Koppel and Palm8 and later Shorter et al.7 quite successfully applied Eq. (1) to a variety of reaction types. The Kamlet and Taft group of workers11 used the alternative Eq. (2): log k = A0 + sπ* + aα + bβ (2) in which π* is a measure of solvent dipolarity/polarizability, β represents the scale of the solvent hydrogen bond acceptor basicity, α represents the scale of the solvent hydrogen bond donor acidity and A0 is the regression value of the solute property in the reference solvent, cyclohexane.
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