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Novel carriers for dicarboxilic acids on the basis of α-aminophosphonates and calix[4]arenes

Novel carriers for dicarboxilic acids on the basis of α-aminophosphonates and calix[4]arenes. Ivan I.Stoikov, Igor S.Antipin, Alexander I.Konovalov. Source Phase. Membrane Phase. Receiving Phase. Membrane Transport. Substrate. Carrier. Substrate-Carrier Complex.

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Novel carriers for dicarboxilic acids on the basis of α-aminophosphonates and calix[4]arenes

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  1. Novel carriers for dicarboxilic acids on the basis of α-aminophosphonates and calix[4]arenes Ivan I.Stoikov, Igor S.Antipin, Alexander I.Konovalov MOLECULAR RECOGNITION

  2. Source Phase MembranePhase ReceivingPhase MembraneTransport Substrate Carrier Substrate-Carrier Complex MOLECULAR RECOGNITION

  3. Receptor forOrganic Acids MOLECULAR RECOGNITION

  4. Dicarboxylic Acids α-Hydroxy Acids α-Amino Acids ? ? ? Receptor Receptor Receptor Hydroden Bonding & Electrostatic Interactions MOLECULAR RECOGNITION

  5. N R1 R2 R3 R4 P, ppm. Yields (%) 1 CH2Ph -(CH2)5- С5Н11 29 75 2 CH2Ph -СН3 -СН3 С2Н5 32 83 3 СН(СН3)2 -СН3 -СН3 С2Н5 31 79 4 CH2Ph -(CH2)4- С5Н11 31 88 5 CH2Ph -СН3 -СН3 С5Н11 34 87 6 CH2Ph -(CH2)4- СН2СН(С2Н5)С4Н9 33 70 7 CH2Ph -(CH2)5- СН2СН(С2Н5)С4Н9 32 72 8 CH2Ph -СН3 -СН3 СН2СН(С2Н5)С4Н9 34 87 9 CH2Ph -СН3 -Н СН2СН(С2Н5)С4Н9 28 67 10 CH2Ph -Н -Н СН2СН(С2Н5)С4Н9 28 73 11 CH2Ph С4Н9 -Н СН2СН(С2Н5)С4Н9 28 62 12 CH2Ph СН3 СН3 С10Н21 30 90 13 CH2Ph -Н -Н С10Н21 30 57 14 CH2Ph -(CH2)5- c-C6H11 28 76 15 CH2Ph Н Н c-C6H11 28 78 Phosphorus Chemical Shifts and Yields of ‑Aminophosphonates MOLECULAR RECOGNITION

  6. Cylinder with membrane Termostated cell MembraneTransport Glass thermostated cell for membrane extraction: 1-external thermostated vessel with source phase; 2-internal vessel with receiving phase; 3-ring; 4-supported liquid membrane (SLM); 5-magnetic stir bars; 6-flow-through cell; D-detector. MOLECULAR RECOGNITION

  7. Initial Glycolic Acid Fluxes through a Supported Liquid Membrane Impregnated by carrier: carrier X R J.106 , mol h-1 cm-2 no carrier - - 0.6 4 С5Н11 2.4 6 СН2СН(С2Н5)С4Н9 3.7 1 С5Н11 4.0 7 СН2СН(С2Н5)С4Н9 4.5 14 c-C6H11 3.6 8 СН2СН(С2Н5)С4Н9 7.2 12 С10Н21 9.6 9 СН2СН(С2Н5)С4Н9 11.0 10 СН2СН(С2Н5)С4Н9 13.5 11 СН2СН(С2Н5)С4Н9 24 15 c-C6H11 1.4 13 С10Н21 30 MOLECULAR RECOGNITION

  8. The Complex Structure of ‑Aminophosphonates with ‑Oxy Acid. MOLECULAR RECOGNITION

  9. Carriers: α-Aminophosphonates 1-8. d,l-Glutamic acid, lg P=-3.69, pKa=4.33 Substrates Sodium acetate, lgP=-4.24 Tartaric acid, lgP=-1.95, pKa=2.89 Oxalic acid, lgP=-0.53, pKa=1.25 Glycolic acid, lgP=-1.11, pKa =3.83 Malonic acid, lgP=-0.58, pKa=1.38 Succinic acid, lgP=-0.59, pKa=4.21 d,l-Mandelic acid, lgP=0.64, pKa=3.37 MOLECULAR RECOGNITION

  10. The histogram of enhancement coefficients in the processes of membrane extraction by α-aminophosphonates 1-8. Этап 1 Этап 2 Этап 3 Янв Фев Мар Апр Май Июн Июл Авг Сен Окт Ноя Дек ε 4 3 Дополнительно... MOLECULAR RECOGNITION

  11. The histogram of enhancement coefficients in the processes of membrane extraction by α-aminophosphonates 1-8. ε 2 MOLECULAR RECOGNITION

  12. The histogram of enhancement coefficients in the processes of membrane extraction by α-aminophosphonates 1-8. ε 3 4 1 7 MOLECULAR RECOGNITION

  13. The Influences of Concentrations of Substrate in Source Phase on Initial Fluxes of Organic Acids through a SLM (298K). Malonic acid Glycolic acid Tartaric acid Succinic acid MOLECULAR RECOGNITION

  14. The Influences of Concentrations of Substrate in Source Phase on Initial Fluxes of Organic Acids through a SLM (298K). Oxalic acid Mandelic acid MOLECULAR RECOGNITION

  15. Calix[4]arenes h 11 12 10 MOLECULAR RECOGNITION

  16. (13) R1=-t-Bu, R2=-CH2-Ph, (14) R1=-t-Bu, R2=--CH2-naphtyl, (15) R1=-t-Bu, R2=-9-CH2-Flu, (16) R1=-t-Bu, R2=-trans-CH2-СH=CH-Ph, (17) R1=-t-Bu, R2=-4-CH2-С6Н4-NO2, (18) R1=-t-Bu, R2=-4-CH2-С6Н4-CN, (19) R1=-t-Bu, R2=-4-CH2-С6Н4-COOEt, (20) R1=-t-Bu, R2=-CH2-COOEt, (21) R1=-NO2, R2=-CH2-Ph (22) R1=-t-Bu, R2=4-CH2-Pyr (23) R1=-t-Bu, R2=-CH2-CH2-NH-C(O)-С6Н5 MOLECULAR RECOGNITION

  17. The histogram of enhancement coefficients in the processes of membrane extraction by calix[4]arenes 13-23 ε ε MOLECULAR RECOGNITION

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