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Effect of Dielectric Constant on Protonation Equilibria of l-Aspartic Acid and Ethylenediamine in 1,2-Propanediol–water Mixtures

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Abstract

Solute–solvent interactions of l-aspartic acid and ethylenediamine have been studied in various concentrations (0–60 % v/v) of 1,2-propanediol–water mixtures maintaining an ionic strength of 0.16 mol l−1 at 303 ± 0.1 K using pH-metric method. The protonation constants have been calculated with the computer program MINIQUAD75. Selection of the best fit chemical model of the protonation equilibria is based on SD in protonation constants and residual analysis using crystallographic R-factor and sum of squares of residuals in all mass balanced equations. Linear variation of protonation constants with inverse of dielectric constants of the solvent mixture has been attributed to the dominance of the electrostatic forces. Distribution of species, protonation equilibria and effect of influential parameters on the protonation constants has also been presented.

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References

  1. Babu MS, Rao GN, Ramana KV, Rao MSP (2000) Solvent effect on protonation equilibria of l-ornithine and l-glutamic acid. J Indian Chem Soc 77:380–385

    Google Scholar 

  2. Latha MP, Rao VM, Rao TS, Rao GN (2007) Determination of protonation constants of l-glutamic acid and l-methionine in 1,2-propanediol–water mixtures. Acta Chim Slov 54:160–165

    Google Scholar 

  3. Rao PS, Srikanth B, Rao VS, Sastry CK, Rao GN (2009) Protonation equilibria of l-aspartic, citric and succinic acids in anionic micellar media. Eur J Chem 6:561–568

    Google Scholar 

  4. Hine J (1975) Structural effects on equilibria in organic chemistry. Wiley, New York

    Google Scholar 

  5. Chen PE, Geballe MT, Stansfeld PJ, Johnston AR, Yuan H, Jacob AL, Snyder JP, Traynelis SF, Wyllie DJA (2005) Structural features of the glutamate binding site in recombinant NR1/NR2A N-methyl-d-aspartate receptors determined by site-directed mutagenesis and molecular modeling. Mol Pharmacol 67:1470–1484

    Article  Google Scholar 

  6. Nelson DL, Cox MM (2000) Lehninger principles of biochemistry, 3rd edn. Worth Publishing, New York

    Google Scholar 

  7. Wang J, Wang J, Liu J, Wang S, Pei J (2010) Solubility of d-aspartic acid and l- aspartic acid in aqueous salt solutions from (293 to 343) K. J Chem Eng Data 55:1735–1738

    Article  Google Scholar 

  8. Tapiero H, Mathe G, Couvreur P, Tew KD (2002) Glutamine and glutamate. Biomed Pharmacother 56:446–457

    Article  Google Scholar 

  9. Kumar NV, Rao GN (2010) Influence of dielectric constant on protonation equilibria of l-aspartic acid in acetonitrile- and ethylene glycol–water mixtures. Acta Chim Slov 58:342–346

    Google Scholar 

  10. Eller K, Henkes E, Rossbacher R, Hoke H (2005) Ulmann’s encyclopedia of industrial chemistry. Wiley, Geneva

    Google Scholar 

  11. Paoletti P (1984) Formation of metal complexes with ethylenediamine: a critical survey of equilibrium constants, enthalpy and entropy values. Pure Appl Chem 56:491–497

    Article  Google Scholar 

  12. Arash L, Habibi MH, Harrington RW, Morteza M, William C (2006) Synthesis, structural and spectroscopic properties of a new Schiff base ligand N,N′-bis (trifluoromethylbenzylidene) ethylenediamine. J Fluorine Chem 127:769–775

    Article  Google Scholar 

  13. Bjerrum J (1950) On the tendency of the metal ions toward complex formation. Chem Rev 46:381–387

    Article  Google Scholar 

  14. Everett DH, Pinsent BRW (1952) The dissociation constants of ethylenediammonium and hexamethylene diammonium Ions from 0° to 60 °C. Proc R Soc Lond 215:416–429

    Article  ADS  Google Scholar 

  15. Kumar NV, Rao GN (2011) Effect of dielectric constant of medium on protonation equilibria of ethylenediamine. Chem Speciat Bioavail 23:170–174

    Article  Google Scholar 

  16. Sigel H, Martin RB, Tribolet R, Haring UK, Balakrishnan RM (1985) An estimation of the equivalent solution dielectric constant in the active-site cavity of metalloenzymes dependence of carboxylate–metal-ion complex stabilities on the polarity of mixed aqueous/organic solvents. Eur J Biochem 152:187–194

    Article  Google Scholar 

  17. Sengwa RJ, Chaudary R, Mehrotra SC (2001) Microwave dielectric relaxation study of poly(propylene glycol) in dilute solution. Mol Phys 21:1805–1812

    Article  ADS  Google Scholar 

  18. Chandraleela A, Swarooparani R, Rao GN (2012) Solvent effect on protonation equilibria of l-aspartic acid and ethylenediamine in dioxan–water mixtures. Proc Natl Acad Sci India Sect A Phys Sci 82:197–204

    Article  Google Scholar 

  19. Rao RS, Rao GN (2005) Computer applications in chemistry. Himalaya Publishing House, Mumbai, pp 277–351

    Google Scholar 

  20. Rao GN (1989) Complex equilibria of some biologically important metal ions in aquo—organic media. Ph. D. Thesis, Andhra University, Visakhapatnam

  21. Gans P, Sabatini A, Vacca A (1976) An improved computer program for the computation of formation constants from potentiometric data. Inorg Chim Acta 18:237–239

    Article  Google Scholar 

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Acknowledgments

RSR and ACL thank the University Grants Commission, Government of India, New Delhi for financial support.

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  1. Department of Inorganic & Analytical Chemistry, Andhra University, Visakhapatnam, 530003, India

    R. Swaroopa Rani, A. Chandra Leela & G. Nageswara Rao

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  1. R. Swaroopa Rani
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  2. A. Chandra Leela
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  3. G. Nageswara Rao
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Correspondence to G. Nageswara Rao.

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Swaroopa Rani, R., Chandra Leela, A. & Nageswara Rao, G. Effect of Dielectric Constant on Protonation Equilibria of l-Aspartic Acid and Ethylenediamine in 1,2-Propanediol–water Mixtures. Proc. Natl. Acad. Sci., India, Sect. A Phys. Sci. 82, 313–316 (2012). https://doi.org/10.1007/s40010-012-0047-3

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  • DOI: https://doi.org/10.1007/s40010-012-0047-3

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