A Study on Complexation of Heavy Metal Ionswith Podands

전체 글

(1)Journal of the Korean Chemical Society 2001, Vol. 45, No. 2 Printed in the Republic of Korea.

(2) *

(3) †.

(4) (2000. 12. 28 ). ‡. †. ‡. A Study on Complexation of Heavy Metal Ions with Podands Kyuseong Choi*, Donghyun Kang, Yongseong Kim, Shimsung Lee†, and Whang Huh‡ Division of Fine Chemistry and Chemical Engineering, Kyungnam University, Masan 631-701, Korea † Department of Chemistry, Kyungsang University, Chinju 660-701, Korea ‡ Department of Chemistry, Ulsan University, Ulsan 680-749, Korea (Received December 28, 2000). . tri(phenylthio-2-ethyl)amine (Podand N S ) tetra(phenylthio tris(2-benzylaminoethyl)amine (Podand N ) !" # $%. &' () *" +, -./ ' 01

(5) (protonation constant)2 Zn(II), Cd(II), Pb(II), Hg(II) (3 451"/ 67 89

(6) :, *" : +,' 95% MeOH ;</= >?@ AB C;D DE ,F 39/= G$%. / ' *" +, -. 01

(7) Podand N S , ,H IJ KLM%. *" +, -./ 6N 01

(8) OP QRS, Zn(II), Cd(II), Pb(II), Hg(II) (3 45 1"/ 67 89

(9) IT, UVW, UXYW Z [\ Podand N S <Podand N S < Podand N ]^Y _, `$%. 1. 3. 2-ethyl)ethylenediamine (Podand N2S4). 4. 2. 1. 3. 2. 4. 4. 4. ABSTRACT. The protonation and stability constants of complexation of Zn(II), Cd(II), Hg(II), and Pb(II) ion with sulfur-containing podand ligands such as tri(2-phenylthioethyl)amine (Podand N1S3), tetra(phenylthio2-ethyl)ethylenediamine (Podand N2S4), tris(2-benzylaminoethyl)amine (Podand N4) have been determined by potentiometric titration in 95% methanol at variable temperatures. From these studies, we observed that podand N4 ligand showed the largest protonation constant. Protonation constant, stability constant, enthalpy, entropy of Zn(II), Cd(II), Hg(II), and Pb(II) ions increased with the following order podand N1S3<podand N2S4<podand N4.. . 16. ab cT (3 d e" !5) fgA^Y h !( ,i' jYk lm d !"/ n' o, pq nr s t%. e K, S u acyclic oligoether open-chain (v, ()q w ISk /x7K Iyz {| } , ~-, -, -~1-13. 13. 14. ^Y o" ! 2 A^Y cC' " ,F t ^Y

(10) %. F F ` () 45 1"/ n' o: ` ;</= 45 1"/ n' [A S h, -. R, 45 2 o h, -/= (3 ( }, e! -./=

(11) ( , fg >/ ;, ?} , ; . 15. 17,18. 19,20. 21-23. 24,25. 26. 27. 131. 28. 29.

(12)

(13) . 132. cT ;/= u;" T ;9: _,\ " ¡(3 (;' cT!" ¢( t%. £ ;</= () 45 1"/ 67 89

(14) / n' o ? DE o T¤( ¥ ^ Y= {Y >( e (3

(15) ^Y >T> 99, ¦¦9B, §mB, ¨SY©WB >?@ AB ¢^Y p( o¥ t%. ISk /x72 *(3

(16) ª «;q {Y (3-¬ / ®FP, ¯°± (3¢q h!/ ²A 8' 45 1"'%. T (3 fg"q {Y (3--F³ aA IT & HSAB |´ ¢/ lµ¥v, cT ¯°± ¶· 45 ¸ ¶·T ¹º, ¯°± @ ¢( e»' Y «;'%. EK cT ¯°± ¶· d ) T ("~2 ISk /x72 45 o d ¼ fg"/ n' o ¸ ½ ¾(%. &' ²1 ¨/x7 ¿À 45 1"\ ÁÂÃ ÄT C( ÅgÆ

(17) ª«;/ cC(pseudo-cavity) PÇ% ¿ÈÉ t%. ÊË Ì {| } , ~-^Y ! / n' o w ¥Í tF Î Ï(v, ()q {| } , ~-, -, -~ ^Y o" ! 2 A^Y cC ' " ,F t ^Y

(18) %. 6S= ¤ o/= ÊË Ì {| } , Fig. 1 Ð( ~ 1|2 3|Y (ÑÍÒ Podand N S [tri(phenylthio-2-ethyl)amine] ~ 2|2 4|Y (ÑÍÒ Podand N S [tetra(phenylthio-2-ethyl)ethylenediamine] Podand N [tris(2-benzylaminoethyl) amine] gD, () *" +, -./ ' 0 1

(19) (protonation constant)2 Zn(II), Cd(II), Hg(II) 30. 31. 32. 33. 36-38. 36. 36. 37. 38. 38. 39. 15. 16. 1. 2 4. 4. . 34. 35. 14. d Pb(II) (3 45 1"/ 67 89

(20) d [ S: >?@ AB §mB^Y G$%. (Y ÊË Ì {| } Ó. / 67 45 1"/ ¶ ÔÂ¢ Õ$%.. 3. . Podand N S , Podand N S , Podand N : !"T ?D C;' 1. 3. 2. 4. 4. triethanolamine, tetraethanolethylenediamine, thionyl-. (CH ) NOH Junsei Chemical Co. Ö \× C;$%. >?@ A ØT ?= C;' MeOH AldrichC HPLC; ZnCl , CdCl , PbCl , HgCl 2 NaClO ÙH O E. MerckC GRÖ C;$%. . !"q ½Ú Á B .;D !"$%. Podand N ¸ tris (2-aminoethyl)amine 9.67 g ÛD 100 mL benzene ;/ Ü$%. Dropping ;< benzaldehyde 22.44 g ÛD benzene ; 20 mL/ ÜD= P)Ý^v, Dean-Stark H¶: C;D 24\ 8 ·º\Þ%. NaBH 7.57 g(0.2 mole)/in MeOH 100 mL: P)Í = Ï3/= ¼ß à"5/ á 8\ 8 ·º\Þ %. Ï3/= ¼ß â pH 2~3 9Y " ã ä F c-HCl åÍæÈ= çÍè éê ëÍ: 5 etherY ÜD= ì>5 íEè%. methanol Y Ü â ether: îÍ= è ïðê Ä NaOH × 15 g 5 20 mL/ ÜD ññ£ A\ 30 òÍó â DCM^Y 3ô $%. 2\ -9 vacuum íÍ{ K= ]' õê ö÷ 1ø à"5 çÝ%. chloride, thiophenol, benzylmercaptan, EtOH, 3 4. 2. 2. 2. 4. 2. 2. 11,12). 4. 4. Fig. 1. Structures of nitrogen-sulfur donor podands. Journal of the Korean Chemical Society.

(21) ! "#. 133. Table 1. IR, 1H-NMR, and 13C-NMR data of podands Podands. 1. 13. C-NMR (CDCl3)a). H-NMR (CDCl3). IR (KBr). Podand N1S3. 3060 cm−1 (C-H, m, aromatic) 2950 cm−1 (C-H, m, aliphatic) 1590 cm−1 (C=C, s, aromatic) 1150 cm−1 (C-S, m, allyl) 740 cm−1 (C-S, s, allyl). δ7.40-7.20 (m, 15H, aromatic) δ3.10-3.00 (t, 8H, NCH2) δ2.75-2.65 (t, 6H, SCH2). δ136.2 (α) 53.5 (NCH2) δ126.0 (o) 31.7 (SCH2) δ128.8 (m) δ129.2 (p). Podand N2S4. 3010 cm−1 (C-H, m, aromatic) 2960 cm−1 (C-H, m, aliphatic) 2815 cm−1 (C-N, m, aliphatic) 1582 cm−1 (C=C, s, aromatic) 1100 cm−1 (C-S, m, allyl) 735 cm−1 (C-S, s, allyl). δ7.82-7.10 (m, 20H, aromatic) δ3.02-2.89 (t, 8H, NCH2) δ2.80-2.65 (t, 8H, SCH2) δ2.52 (s, 4H, NCH2). δ136.3 (α) δ53.8 (NCH2) δ126.0 (o) δ52.8 (SCH2) δ128.9 (m) δ31.6 (NCH2) δ129.2 (p). Podand N4. 3010 cm−1 (C-H, m, aromatic) 2960 cm−1 (C-H, m, aliphatic) 2815 cm−1 (C-N, m, aliphatic) 1582 cm−1 (C=C, s, aromatic). δ7.82-7.10 (m, 20H, aromatic) δ3.02-2.89 (t, 8H, NCH2) δ2.52 (s, 4H, NCH2). a). Park, J. M. M. S. Thesis, Gyeong-Sang Univ, 1995.. () ù ) IR H-NMR C-NMR ÅúXû " W(I) Table 1/ KLü%. !"' Podand N S , Podand N S 2 Podand Varian N : #T ?D NMRq 200 MHz Gemini 200 400 MHz Varian Gemini 400, IRq Shimazu FT-IR 8000 C;$%. *" + , -./ 6N 01

(22) 2 45 1"/ 67 8 9

(23) Gq >?@ A H¶ Orion 960 Autochemistry system C;$, >q c > ÀYý > þ! >(Orion Combination Electrode Cat. No. 81-02) C;D G$^v, ; < 39 15.0~35.0 C(±0.1 C)Y cF$%.

(24) . >?@ Aq 2 ÿT 9, 1.010 M 95% MeOH;< 25.0 mL, ¥9 ó², ~ ?T/= 3.010 M KOH T: 0.1 mL A,= ;< pH: G$%. pH Gq OrionC ;<(pH=7.0, 4.0)^Y `' â C;$%. NaClO ÙH OY (3 9: 0.1Y Ý, 39 15.0~35.0 C(±0.1 C)/ = G$%..

(25) mq A. E. Martell ¢( P)Í è BEST

(26) Y (;D m$%. ( Y q , , T ÿT 9: F n 01

(27) : Y { A, T ;</ 6N pH: ,

(28) Z éY m 1. 13. 1 3. 2 4. 4. o. o. −4. −3. 4. 2. o. 40. 2001, Vol. 45, No. 2. o. ( pH Z G' pH Z @(: ¾@(σ) Y m'%. ( Z( I

(29) Z Y Ó \ = Ðq m -þD ¾@, aY ¥ 0 1

(30) Z h ó%. . 45 89

(31) ÿT ;</ 2 (/ e (3 Zn(II), Cd(II), Hg (II), Pb(II) (3 9, 1.010 M( ¥9D *" +, -. 01

(32) G ÷' ÁB ^Y G'%. £ ²B(K, H. Rossotti ¼ (;D 45 " oF ÎS9 BEST Y (;D, 451"/ 67 (3 " d 89

(33) : o t%. . e (3) 2 45 1"/ 67 [ S ∆H2 ∆S Zq >? @ AB^Y DE 39/= 89

(34) : o, %¡ ¼ (;D o t%. DE 39/= 89

(35) : o, %¡ ¼ ( ;D ∆H2 ∆S: o t%. −4. 41. ∆G = –RT ln K. (1). = ∆H – T ∆S. (2). DT= R = 8.314 J/mol K: , ¼ (3)^Y %\ t%. 1 ∆H ∆S logK = – ------------------- ⋅ --- + ------------------19.1415 T 19.1415. (3).

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(37) . 134. ]^Y _,$, ( IT2 {| } Y «; ~ } , nmt ^Y G t%. Podand N S `% {| } ~ } 2 } , 1| pq Podand N S (X _,Y D Z `%. &' Podand N Podand N S , Podand N S `% *" , +, t ~ } , K, ù|, t¡^Y = *" +, -./ 67 01

(38) Zq IJ KL%. Podand N S ¸ *" +, -. 01

(39) log KH ( log KH `% Z `(, ( !" *" +, -.( ÷Í # ä ( *" ¥Í t *> ä½/ >TA -$( ÷ÍK, ( ä % &'( 9/ 6S !" 01

(40) Z( )!" 01

(41) Z/ ² «q Z *T ä½(%. Zn(II), Cd(II), Hg(II), Pb(II) (3 ) 45 1"/ 67 89

(42) *" +, -. 01

(43) : o ÁB ÷J 2 (3( )Í t ;</= >?@ A Ø$^v, N : +A A ,f^Y Fig. 2/ ÏÝ%. “BEST” Y (;D o' 45 89

(44) Zq Table 3 KLü^v, / 6N (3 89

(45) (3 ° ]^Y _ Podand N S <Podand N S <Podand N ,$%. ( *" +, -. 01

(46) Z( ,H Podand N , ,H 89

(47) : ` D (3) 8' 45 1" t¡ `D{ ^Y, *" +, -. 01

(48) ~ } / ' T9 -9, ¥ v (3 45 1" -./ ' 89

(49) / ÔÂ ì ¿ t%. &' Podand N {| } _,/ 67 (X Y ,H 89: `( t%. Podand N S ` % {| } ~ } 2 } , 1| p 1. 3. 2. 4. 1. 3. 2. 2. 4. 4. 4. 1. 2. 4. 40. Fig. 2. The titration curves for complexes of Podand N4 at 25 oC.. ¼ (3) (;D 1/T/ D log K: 9\, ¾ TTY ∆H2 ∆S: o t%.. >?@ AB/ D 95% MeOH ;</= Podand N S , Podand N S 2 Podand N / ' *" +, -. 01

(50) : 39Ó / 6S GD Table 2/ KLü%. ( h *" 01

(51) Zq Podand N S <Podand N S <Podand N 1. 3. 2 4. 1. 3. 4. 2. 4. 4. 1. 3. 2. 4. 4. 4. 4. 1. 3. Table 2. Protonation constants of podands in 95% MeOH at variable temperatures Podand N1S3 10 oC 20 oC 25 oC 35 oC. 5.08 4.51 4.23 3.82. Podand N2S4. Podand N4. log KH1. log KH2. log K. log KH1. log KH2. log KH3. log KH4. log K. 6.54 6.40 6.35 6.19. 4.71 4.26 4.08 3.79. 11.25 10.66 10.43 19.99. 7.65 7.51 7.46 7.30. 6.55 6.10 5.92 5.63. 2.39 2.25 2.20 2.04. 2.00 1.93 1.88 1.67. 20.58 17.79 19.69 19.43. Journal of the Korean Chemical Society.

(52) ! "# Table 3. Stability constants of complexation of metal ions with podands in 95% MeOH solutions at variable temperatures. . Podand N1S3 Podand N2S4. Podand N4. (oC). log K. log K. log K. Zn(II). 10 20 25 35. 7.45 7.08 6.76 6.43. 11.18 10.51 10.38 10.08. 18.32 18.09 17.85 17.35. Cd(II). 10 20 25 35. 7.63 7.14 7.09 6.91. 11.44 11.21 10.97 10.48. 18.77 18.42 18.08 17.60. 15 20 25 35 10 20 25 35. 7.38 6.86 6.64 5.56 7.29 7.06 6.96 6.72. 11.01 10.64 10.19 19.62 13.34 12.83 12.45 12.19. 18.28 17.98 17.63 17.15 20.58 20.07 19.69 19.43. Pb(II). Hg(II). 4. 1. 1. 3. 3. 2 4. 4. ¢q, (3 > 9, 7 8 ' 45 1"'% $%. 8, (3 > 9, 7 (3 IT, « 45 89 I% (%. Lumb2 Martell q 89

(53) IT (3 92@ (3 /: F IT ]=S $%. &' Izatt ¢ q (3 >T¡"9 IT ]=Y 45 89

(54) , 2Ò% $%. 45 1" -./ ' UVW Ó (3 {| } ~2 } C( h!/:F, 2 45/= T oA /:F, (3 ; UVW¢ È %. Zn(II), Cd(II), Hg(II) Pb(II) (3/ ' ) UVW Ó Table 42 Ð( ° ¡ Z `( tÍ $ -. ¿ t ^v, UXYW 45 1" \ T oA Ó d (3 V; ;

(55) / h%. Popov ¢q 1, *(3 crown ether 2 45 -.( ¡ ∆S Z *% $%. (cY 1, *(3q MeOH2 Ðq o" ;m/= ; <^Y= ; oA n>^Y ‘Structure-breaking ’: {FP, DT/ crown ether, +,¥Í *(3 45 1" *(3q ; ? @J ¥ 45 crown ether " ÊË ;2 "

(56) ª «; v h ‘Structure-making ’: *T ä½(S $%. wT/ ² 2, *(3 azacrown ether 2 45 -.q * ∆S Z `( t%. (cY azacrown ether ; , 2, *(3( +,</ 6S ; 9, A</ 6S, 8 V; ;

(57) ( _,</ 6S ∆S Zq _,'% $%. ∆S Zq Table 5 Ð( Podand N S , Podand V. Vrikel42. 43. 44. 45,46. q Podand N S (X _,Y D `% ./ 89

(58) : ,~ ^Y G¥Ý^K, Y Podand N S / ² 0/ Z `(F Î1%. ( {| } _,Y ' (X ./ 23^K, IT _,/ 67 A H4, Y IJ «;D G`% «q Z ` ( Q5, D6Ò%. e (3 Zn(II), Cd(II), Hg(II), Pb(II) (3 ²D `, Podand N S ¸ Cd(II)> Hg(II)>Zn(II)>Pb(II) ]^Y, Podand N S 2 Podand N ¸ Hg(II)>Cd(II)>Zn(II)>Pb(II)]^Y 451 "/ 67 89

(59) Z `( t%. 45 89

(60) / ÔÂ ¶ *(3 Y 2. 135. 47. 48,49. 1. 3. Table 4. Comparision of physical data of metal(II) ions. Zn(II) Cd(II) Pb(II) Hg(II) a). Ionic radiusa) (Å). 2nd ionization energyb)(MJmol−1). Electronegativityc). 0.74 0.97 1.10 1.21. 1.7333 1.6314 1.8097 1.4504. 1.65 1.69 2.00 2.33. : Shannon, R. D. Acta Crystallorg. 1976, A32, 751. : Moore, C. E. “Ionization Potentials and Ionization Limits Derived from the Analyses of Optical Spectra.” c) : Pauling, L. “The Nature of the Chemical Bond.” 3rd, p 93. b). 2001, Vol. 45, No. 2.

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(62) . 136. Table 5. Thermodynamic parameters of Zn(II), Cd(II), Pb(II), and Hg(II) complexes with podands Zn(II). Cd(II). Pb(II). Hg(II). Podand N1S3. log K −∆H(kJ/mol) T∆S(kJ/mol) ∆G(kJ/mol). 6.76 75.85 −36.27 −39.58. 7.09 28.22 11.93 −40.15. 6.64 51.72 −26.25 −25.47. 6.96 38.54 −3.68 −34.86. Podand N2S4. log K −∆H(kJ/mol) T∆S(kJ/mol) ∆G(kJ/mol). 10.38 84.38 −25.24 −59.14. 10.97 87.99 −24.98 −63.03. 10.19 72.64 −56.61 −16.03. 12.45 79.24 −24.62 −54.62. Podand N4. log K −∆H(kJ/mol) T∆S(kJ/mol) ∆G(kJ/mol). 17.85 85.54 −57.77 −27.77. 18.08 101.65 6.14 −95.51. 17.63 99.04 −6.16 −92.88. 19.69 79.08 −114.57 −64.51. ¸, Zn(II), Pb(II), Hg(II) (3/= ¡ Z `( tÍ V; ;

(63) `% c"( AD `% ' o: *J ¥v, &' ;2 "

(64) ª «;^Y ' ‘Structuremaking ’, `% ¸BJ «;' ^Y G %. wT/ ² Cd(II) (3/= ∆S Z( * Z `( tÍ V; ;

(65) , 8 Cd(II) (3/ ; ¥Í tC ; , p( åÍÉ Kö ;

(66) ( `% ¸BJ «;' ^Y G%. ÍD ( ÒØã ,i"q ∆H, `% ¡ Z(w K Eq ∆S, `% * Z÷ _,'%. Zn(II)( 3/= UVW (X 45 à" cJ P)FP UXYW EF FD UVW ÔÂ p( %q -, Cd(II) (3/= UVW2 UXYW *G ° , (X 45 à"/ c J «;$%. N4. {| } Y } : *" +, -./ ' 01

(67) 2 Zn(II), Cd(II), Pb(II) d Hg(II) 45 1"/ 6N 89

(68) d [A S: o¤ h %¡ Ðq h çÝ%. )", *" +, -./ ' 01

(69) Podand ]^Y Z ` N S <Podand N S <Podand N $, ( Podand N , *" , +, t ~ } , tÍ Z ` (%. 1. 3. 2. 4. 4. 4. H", 45 89

(70) Zq (3 ° ]^Y Z `$, ( {| } ~ } 2 } _,Y ' (X , _,' ä½(%. I", UVW Ó Z(−∆H)q (3 ° ¡ Z `( tÍ $ -. ¿ t^v, UXYW Ó Z(∆S)q Podand N S , Podand N / = Zn(II), Pb(II), Hg(II)/= (-) Z ,J `Q 45 1"\ UVW , ¸BJ «;$, Cd (II) (3/= (+)Z * ^Y `Q UVW2 UXYW , ° «;$%. Podand N1S3<Podand N2S4<Podand N4. 1. 3. 4. K Ìo²2 1998K Lo"² F}/ D o¥Ý^MY (/ A CyR%. 1997. 1. (a) Cram, D. J.; Cram, J. M. Science 1990, 108, 803. (b) Izatt, R. M.; Bradshaw, J. C. Chem. Rev. 1991, 91, 1721. (c) Inoue, Y.; Gokel, G. W. Cation Binding by Macrocycle; Dekker, 1990. 2. Curtis, W. D.; Laidler, D. A.; Stoddart, J. F. J. Chem. Soc., Perkin I 1977, 1756. 3. Hu, S.; Mukherjee, A.; Spiro, T. G. J. Am. Chem. Soc. 1993, 115, 12366. 4. Perderson, C. J. ibid. 1967, 89, 7017. 5. Frendorff, H. K. ibid. 1971, 93, 600. 6. Lehn, J. M.; Sauvage, J. ibid. 1975, 97, 6700. 7. Arnaud-Neu, F.; Spiess, B.; Schwing-Weill, M. Helv. Journal of the Korean Chemical Society.

(71) ! "# Chim. Acta 1977, 60, 2633. 8. Arnaud-Ner, F.; Spiess, B.; Schwing-Weill, M. J. Am. Chem. Soc. 1982, 104, 5641. 9. Richman, J. E.; Atkins, T. J. ibid. 1974, 96, 2268. 10. Kodama amd, M.; Kinura, E. Inorg. Chem. 1980, 19, 1871. 11. (a) Armstrong, L. G.; Lindoy, L. F. ibid. 1975, 14, 1322. (b) Adam, K. R. et al. J. Am. Chem. Soc. 1983, 105, 4645. (c) Lindoy, L. F.; Lip, H. L.; Power, L. F. Inorg. Chem. 1976, 15, 1724. 12. (a) Adam, K. R.; Anderegg, G. ibid. 1981, 20, 4048. (b) Lindoy, L. F. ibid. 1980, 19, 3360. 13. Vogtle, F.; Weber, E. J. Am. Chem. Soc. 1977, 99, 4683. 14. (a) Meada, H. Bull. Chem. Soc. Jpn. 1983, 56, 212. (b) Hogberg, S. A. G.; Cram, D. J. J. Org. Chem. 1975, 40, 151. (c) Lehn, J. M. U. S. Patent 3. 1975, 877, 888. 15. Perderson, C. J. J. Org. Chem. 1971, 36, 254. 16. Pellissard, D.; Louis, R. Tetrahedron Lett. 1972, 4589. 17. Cox, B. G.; Knop, D.; Schneider, H. J. Phys. Chem. 1980, 84, 470. 18. (a) Abraham, M. H. et al. J. Chem. Soc., Faraday I. 1980, 76, 869. (b) Cox, B. G.; Schneider, H. J. Phys. Chem. 1980, 84, 470. 19. Gresser, R. J. Am. Chem. Soc. 1980, 102, 651. 20. (a) Kagenow, H.; Jensen, A. Anal. Chem. 1980, 114, 227. (b) Cox, B. G.; Truong, N.; Schneider, H. J. Am. Chem. Soc. 1984, 106, 1273. 21. Bush, M. A.; Truter, M. R. J. Chem. Soc. 1971, (B) 1441. 22. Malmsten, L. A. Acta. Cryst 1979, B35, 1702. 23. Metz, B.; Moras, D.; Weiss, R. J. Am. Chem. Soc. 1971, 93, 1086. 24. (a) Kirch, M.; Lehn, J. M. Angew. Chem. Int. Ed. Engl. 1975, 14, 555. (b) Kobuke, Y. et al. J. Am. Chem. Soc. 1976, 98, 7414. 25. Lamb, J. D. ibid. 1980, 102, 6820. 26. Gokel, J. W.; Wever, U. P. J. Chem. Edu. 1978, 55, 350. 27. Rchnitz, G. A.; Eyal, E. Anal. Chem. 1972, 44, 370. 28. Jawaid, M.; Lngman, F. Talanta. 1978, 25, 91. 29. Olsherk, U.; Grodzinski, J. J. J. Chem. Soc., Dalton Trans. 1981, 501. 30. Sam, D. J.; Simmons, H. E. J. Am. Chem. Soc. 1972, 94, 4024.. 2001, Vol. 45, No. 2. 137. 31. Abraham, M. H. et al. Acta Chem. Scand. 1980, A34, 621. 32. Loyola, V. M.; Pizer, R. J. Am. Chem. Soc. 1977, 99, 7185. 33. Abraham, M. H.; Danil, A. F.; Schulz, R. A. J. Chem. Soc., Dalton Trans. Faraday I, 1980, 76, 869. 34. Cox, B. G.; Truong, N.; Schneider, H. ibid. 1978, 100, 4746. 35. Kagenow, H.; Jensen, A. Anal. Chem. 1980, 114, 227. 36. Inoue, Y.; Gokel, G. W. Cation Binding by Macrocycles; Dekker, 1990. 37. Perason, R. G. J. Am. Chem. Soc. 1965, 85, 3533. 38. (a) Izatt, R. M.; Lamb, J. D.; Rossiter, B. E.; Izatt, N. E.; Christensen, J. J. J. Chem. Soc., Chem. Commun. 1978, 108, 386. (b) Izatt, R. M.; Lamb, J. D.; Swain, C. S.; Christensen, J. J.; Haymore, B. L. J. Am. Chem. Soc. 1980, 107, 3032. 39. Vogtle, F.; Weber, E. Host Guest Complex Chemistry; Springer-Verlag, 1985. 40. Martell, A. E.; Motekaitis, R. J. Determination and Use of Stability Constants; VCH Publishers: New York, 1992. 41. Rossotti, H. The Study of Iomic Equilibria; Longman: London, 1978; p36. 42. Vrikel, V.; Boer. Rec. Trav. Chim. 1928, 47, 593. 43. Lumb, R. F.; Martell, A. E. J. Phys. Chem. 1953, 57, 690. 44. Izatt, H. M.; Hass, C. G. J. Phys. Chem. 1954, 58, 1133. 45. Hinz, F. P.; Wargerum, D. W. Inorg. Chem. 1974, 13, 2941. 46. Barbucci, R.; Vacca, A. J. Chem. Soc., Dalton Trans. 1974, 2363. 47. Izatt, R. M.; Bradshaw, J. S.; Christensen, J. J. Chem. Rev. 1985, 85, 271. 48. Izatt, R. M.; Christensen, J. J. Progress in Macrocyclic Chemistry. 1979, 1, Willey. 49. Hoogerheide, J. G.; Popov, A. I. J. Soln. Chem. 1979, 8, 83. 50. Kollman, P. A.; Allen, L. C. J. Am. Chem. Soc. 1971, 93, 4991. 51. Latimer, W. M. Oxidation Potentials. 2nd ed; Prentice Hall: N. J., 1952..

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A Study on Complexation of Heavy Metal Ionswith Podands  

A Study on Complexation of Heavy Metal Ionswith Podands