Macroscopic and Microscopic Protonation Equilibria of Some α-Amino Acids in Dimethyl Sulfoxide-Water Mixtures

Doʇan A., ASLAN N., Erden P. E., CANEL E., Klllç E.

Journal of Solution Chemistry, cilt.44, sa.8, ss.1705-1722, 2015 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 44 Sayı: 8
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1007/s10953-015-0363-8
  • Dergi Adı: Journal of Solution Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1705-1722
  • Anahtar Kelimeler: Dimethyl sulfoxide-water mixture, Macroscopic/microscopic protonation constant, Solvent effect, α-Amino acid, α-Amino acid ester
  • Ankara Hacı Bayram Veli Üniversitesi Adresli: Evet

Özet

© 2015 Springer Science+Business Media New York.The acid-base chemistry of multidentate (bio)ligands are usually characterized in terms of macroscopic protonation constants, log10 K (or pK), which are composites of the microscopic constants (log10 k or pk) for the individual groups. In this study, macroscopic protonation constants of some α-amino acid (glycine, l-alanine, l-valine, l-leucine, l-phenylalanine, l-serine) and protonation constants of their methyl- and ethyl- esters in dimethyl sulfoxide-water mixtures (10-40 % dimethylsulfoxide by volume) were studied by potentiometric technique at 25.0 ± 0.1 °C under a nitrogen atmosphere, and at ionic strength of 0.10 mol·L-1 sodium chloride. The protonation constants were calculated by using the Best computer program and the constants were evaluated for microscopic protonation constants of these α-amino acids. The protonation constants are discussed on the basis of solute-solvent interactions. The constants were influenced by changes in solvent composition. The dipolar ionic form, however, still greatly predominates, even in 40 % dimethyl sulfoxide.