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Investigation of the Analytical Properties Op INVESTIGATION OF THE ANALYTICAL PROPERTIES OP SUBSTITUTED ANTHRANILIC ACIDS AND RELATED COMPOUNDS DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University By WILLIAM ALLEN YOUNG, B. A., K. Sc, The Ohio State University 1957 Approved, by: Adviser Department of Chemistry ACKNOWLEDGEMENT The author expresses his appreciation to Dr. T. R. Sweet for his suggestions and interest throughout this investigation and to the Kettering Research Foundation for sponsoring a portion of this work. ii Table of Contents Introduction “ Historical 2 Development of equations 4 Bjerrum's equations 4 Convergence correction 9 Schwarzenbach's graphical method 15 Calvin-Bjerrum pH titration equations 19 Experimental 30 The compounds and their preparations 30 Analysis of the compounds 36 The solvent medium 52 Titration procedures 54 Calibration of the pH meter 54 Study of ionic strength 57 Data 61 Discussion 170 Factors involved in chelate formation 170 Tables of results 178 Discussion of results 183 Properties and analytical uses 197 Summary 203 Appendix: Details of the preparations of the compounds 205 References 216 iii List of Tables No. Page 1 Data for the convergence correction curve 11 2 Data for Schwarzenbach's method of solving k values for N,N' trimethylene dianthranilic acid 17 3 Elementary analysis of the nine prepared compounds 36 4 Equivalent weights of the compounds 37 5-11 Titration data for anthranilic acid 61 - 65 12 - 18 Titration data for N-methyl anthranilic acid 66 - 70 19 - 30 Titration data for 2 ,2 ' imino dibenzoic acid 72 - 82 31 - 41 Titration data for 2,2' hydrazo dibenzoic acid 33 _ go 42 - 53 Titration data for methylene dianthranilic acid 91 _ 99 54 - 69 Titration data for N,N' trimethylene dianthranilic acid 100 _ m 70 - 80 Titration data for N-(aiuinoethyl)-anthranilic acid 112 - 122 81 - 102 Titration data for 2 -(aminomethyl)-benzoic acid 124 - 136 103 - 108 Titration data for salicylic acid 137 - 141 109-119 Titration data for 0-(carboxymethoxy)-benzoic acid 142 - 148 120 - 130 Titration data for N-(carboxymethyl)-anthranilic acid I49 - 160 131 -141 Titration data for anthranilic acid diacetic acid 161 - 169 142 Acidity constants in 50 volume % dioxane .. 178 143 Formation constants of chelates in 50 volume a/o dioxane 179 _ 131 144 Orders of log for the five cations with each of the compounds 182 145 Chelate effects of N,N'ethylene dianthranilic acid 133 146 Chelate effects of N,Nrtrimethylene dianthranilic acid 186 147 Effect of adding -CH^COOH groups to the nitrogen of anthranilic acid 189 iv List of Figures 1 Convergence correction curve 2 Schwarzenbach method graph for N,N' trimethylene dianthranilic acid 15 Infrared spectra of the compounds 16 pH - a curve for anthranilic acid 17 pH - a curve for N-methyl anthranilic acid 18 n - pR curve for H-methyl anthranilic acid and zinc 19 pH - a curve for 2 ,2 ' iinino dibenzoic acid 20 n - pR curve for 2,2' imino dibenzoic acid and cobalt 21 n - pR curve for 2,2' imino dibenzoic acid and copper 22 pH - a curve for 2,2' hydrazo dibenzoic acid 23 pH - a curve for metnylene dianthranilic acid 24 n - pR curve for methylene dianthranilic acid and nickel 25 pH - a curve for N,h' trimethylene dianthranilic acid 26 pH - a curve for H-(aminoethyl)-anthranilic acid 27 pH - a curve for 2-(aminomethyl)-benzoic acid 28 n - pR curve for 2 -(aminomethyl)-benzoic acid and copper 29 pH - a curve for salicylic acid 30 pH - a curve for o-(carboxymethoxy)-benzoic acid 31 pH - a curve for N-(carboxymethyl)-anthranilic acid v 32 n - pR curve for h-(carboxymethyl)-anthranilic acid 155 and copper 33 n - pR curve for N-(carboxymethyl)-anthranilic acid 159 and zinc 34 pH - a curve for anthranilic acid diacetic acid 163 35 n - pR curve for anthranilic acid diacetic acid 166 and nickel 36 Comparison of the stabilities of chelates of H-(amino- 191 ethyl)-anthranilic acid and N-(carboxymethyl)- anthranilic acid 37 Comparison of the stabilities of chelates of H-(amino- 192 ethyl)-anthranilic acid and ethylene dianthranilic acid 38 Comparison of the stabilities of chelates of H-(carooxy- 193 methyl)-anthranilic acid and H,N' ethylene dianthranilic acid 39 Comparison of the stabilities of chelates of 194 N,l\f' trimethylene dianthranilic acid and iJ,H' ethylene dianthranilic acid 40 Comparison of the log values of 2-(aminomethyl)- 195 benzoic with the second ionization potentials of the metals 41 Comparison of the log k^ values of anthranilic acid 196 diacetic acid with the second ionization potentials of the metals vi INTRODUCTION This investigation is one of a group of studies which have been carried out in this laboratory. These studies are concerned with the analytical properties of anthranilic acid, substituted anthranilic acids, derivatives of anthranilic acid, and compounds similar to anthranilic acid. The data obtained should be useful in determing the factors which cause certain analytical organic reagents to be specific or selective ana in the development of analytical methods. The present A'ork is a study of the effects of substitution on the amino group of anthranilic acid. A number of N-substituted anthranilic acids were prepared and acidity constants of these compounds were determined, formation constants of the chelates formed with each of these compounds and a series of transition met;. Is were obtained. In addition to the determination of constants, precipitation and color reactions of these compounds were studied. 1 HISTORICAL The analytical uses of anthranilic acid have been reviewed by- Harris in his dissertation (l). he made a precipitation study which generally confirmed the earlier results found by Goto (2 ). Harris determined the acidity and formation constants of ring-substituted anthranilic acids (l, 3 , 4 ), including 5-sulfo anthranilic acid, 3 -methyl ■anthranilic acid, and 3 ,5-diiodo anthranilic acid. In addition he determined constants for anthranilic acid, li-methyl anthranilic acid, and il-pheriyl anthranilic acid (1,4). Harris prepared N,N' ethylene dianthranilic acid and found that it has constants and other properties which are quite different from anthranilic acid (5) Zhdanov, Tseitlin, and Yakubov (6) described direct amperometric titrations of copper, zinc, nickel, and cobalt using a solution of the sodium salt of anthranilic acid as the titrant. Cimemo.n and belser (7) studied the q u m t i tative broraination of anthranilic acid and gave an exact micro method for the determine tions of metals precipitated by anthranilic acid. Holmes end Crinr.in (o) studied an oxidation titration with nerchloretocerote a.is alr.o a colorj metric reaction as means of deter­ mining the anthranilic acin liber ted from metal aut.ranilc.tes dissolved in acid. Harris (l,3) and Zehner (9,10), studied 5-sulfo anthranilic acid. Zehner developed a spectrophotometric determination of iron usin. this reagent. Romero (ll) investigated the properties of several bromine and iodine-substituted anthranilic acids as gravimetric reagents. Salyer (12) used radiotracer techniques to measure the solu­ bilities of the cobalt precipitates of some of the reagents mentioned above. Datta and Banerjee (13) used N-(carboxymethyl)—anthranilic acid as a precipitant for tuorivmi. fi&ny of the properties of anthr nilic acid diacetic acid have been investigated by 3chw .roenbaeh (l4, 15, 16, 17). Fitch and 2 3 Russell (is) tested it as an eluent for rare earths. 2,2'Imino dibenzoic acid has been suggested as an oxidation reduction indicator (19, 20). The solvent medium used in our titration studies was 50 volume % dioxane-water, and it has also been used by many other workers in this field (21, 22, 23). J. K. Thompson and G. L. Wilson of Queen's University, Belfast, Ireland, presented a paper entitled "Metal-Organic Complexes of Analy­ tical Significance: Stabilities of Complexes of Bivalent Cations with Anthranilic Acid and Its Derivatives" at the XVth International Congress of Pure and Applied Chemistry at Lisbon, Portugal, during the week, September 9-16, 1956 (2 4 ). At the present time (February, 1957) no other details are available. Development of the equations used to calculate the formation constants. Bjerrum (2 5) originally developed the theoretical equations for simple complexes; however, the treatment is the same for chelate complexes. When a metal ion M can react with ligands R, and N is the maximum number of ligands which can become attached to 1*1, then the following stepwise equilibria exist. M + R ^ MR kx = /mR_7/Z"m_7 Z"\7 (i) MR + R £ MR2 k 2 = D^gJ/D^J DO (II) % _ 1 + R < kM - (III) The quantity n is by definition the average number of ligands bound per metal. n = D O + + n /mRmJ' --------------------------------------------------------------(XV) DO + D m J + Z*®2_7 + D ^ y J + Use of equations (i), (ll), and (ill) makes possible the elimination of the quantities DO, O D ^ O D ^ 7 from equation (IV). n = \ D O + Zkjk^IiO2 "* + Hk ^ . k j ^ X T 11 ----------------------- :---------------------- (v) 1 + ^ D O + ^ k ^ K j 2 •••• + kxk2 ••• k / X / In terms of experimentally measured quantities, n can oe written as n =Ca - / \ 7 (VI) is the total concentration of all metal species, and is the total concentration of all ligand species. C,„ and G' are calculated from the l'i J X 4 amounts of metal and of chelating compound known to be present in the solution. Is measured experimentally. Bjerrum discussed the statistical effects entering into successive complex formation. At first it might appear that the successive formation constants K^, etc., would be of equal size when the addition of a ligand to a metal ion does not change the ability of the metal ion to accept more ligands.
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