Research Article

Synthesis and Enantiomeric Recognition Studies of Novel C2-Symmetrical Chiral Tetra-Amide Compounds

Volume: 11 Number: 2 June 1, 2021
EN TR

Synthesis and Enantiomeric Recognition Studies of Novel C2-Symmetrical Chiral Tetra-Amide Compounds

Abstract

Two novel C2-symmetrical chiral tetraamide compounds derived from (S)-isoleucine were synthesised and their enantiomeric recognition abilities towards enantiomers of some amino acid esters and 1-arylethylamins were examined by UV-titration method. These receptor compounds exhibited strong complexation (with Ka up to 5787.23 M-1) and very good enantioselectivity (up to KaS/KaR= 13.98).

Keywords

Supporting Institution

Batman Üniversitesi Bilimsel Araştırma Projeleri Koordinatörlüğü

Project Number

BTUBAP-2018-FED-2

References

  1. Aral H, Aral T, Çolak M, Ziyadanoğulları B, Ziyadanoğulları R,2013. C2-Symmetric chiral diamine ligands for enantiomeric recognition of amino acid esters and mandelic acid by proton NMR titration method. Turkish Journal of Chemistry, 37:374-382. doi: 10.3906/kim-1207-58
  2. Aral H, Çelik KS, Altındağ R, Aral T, 2017. Synthesis, characterization, and application of a novel multifunctional stationary phase for hydrophilic interaction/reversed phase mixed-mode chromatography. Talanta, 174:703-714. doi: 10.1016/j.talanta.2017.07.014
  3. Aydın I, Aral T, Karakaplan M, Hoşgören H, 2009. Chiral lariat ethers as membrane carriers for chiral amino acids and their sodium and potassium salts. Tetrahedron: Asymmetry, 20(2):179-183. doi: 0.1016/j.tetasy.2009.01.005
  4. Bako P, Keglevich G, Rapi Z, Toke L, 2012. The enantiomeric differentiation ability of chiral crown ethers based on carbohydrates. Current Organic Chemistry, 16:297-304. doi: 10.2174/138527212799499877
  5. Ballistreri FP, Pappalardo A, Tomaselli GA, Toscano RM, Sfrazzetro GT, 2010. Heteroditopic chiral uranyl–salen receptor for molecular recognition of amino acid ammonium salts. European Journal of Organic Chemistry, 3806-3810. doi: 10.1002/ejoc.201000566
  6. Bennesi HA, Hildebrand JH, 1949. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. Journal of the American Chemical Society, 71(8):2703-2707. doi: 10.1021/ja01176a030
  7. Bohanon TM, Caruso PL, Denzinger S, Fink R, Mobius D, et al., 1999. Molecular recognition-induced function and competitive replacement by hydrogen-bonding interactions: Amphiphilic barbituric acid derivatives, 2,4,6-triaminopyrimidine, and related structures at the air−water interface. Langmuir, 15(1):174-184. doi: 10.1021/la980348w
  8. Chadwick DJ, Cliffe IA, Sutherland IO, Newton RF, 1984. The formation of complexes between aza derivatives of crown ethers and primary alkylammonium salts. Part 7. Chiral derivatives of aza crown ethers. Journal of the Chemical Society, Perkin Transactions 1, 1707-1717. doi: 10.1039/P19840001707

Details

Primary Language

English

Subjects

Chemical Engineering

Journal Section

Research Article

Publication Date

June 1, 2021

Submission Date

September 30, 2020

Acceptance Date

December 31, 2020

Published in Issue

Year 2021 Volume: 11 Number: 2

APA
Sünkür, M., Tiğiz, Z., Cebe, D., & Aral, T. (2021). Synthesis and Enantiomeric Recognition Studies of Novel C2-Symmetrical Chiral Tetra-Amide Compounds. Journal of the Institute of Science and Technology, 11(2), 1293-1301. https://doi.org/10.21597/jist.802116
AMA
1.Sünkür M, Tiğiz Z, Cebe D, Aral T. Synthesis and Enantiomeric Recognition Studies of Novel C2-Symmetrical Chiral Tetra-Amide Compounds. J. Inst. Sci. and Tech. 2021;11(2):1293-1301. doi:10.21597/jist.802116
Chicago
Sünkür, Murat, Züleyha Tiğiz, Deniz Cebe, and Tarık Aral. 2021. “Synthesis and Enantiomeric Recognition Studies of Novel C2-Symmetrical Chiral Tetra-Amide Compounds”. Journal of the Institute of Science and Technology 11 (2): 1293-1301. https://doi.org/10.21597/jist.802116.
EndNote
Sünkür M, Tiğiz Z, Cebe D, Aral T (June 1, 2021) Synthesis and Enantiomeric Recognition Studies of Novel C2-Symmetrical Chiral Tetra-Amide Compounds. Journal of the Institute of Science and Technology 11 2 1293–1301.
IEEE
[1]M. Sünkür, Z. Tiğiz, D. Cebe, and T. Aral, “Synthesis and Enantiomeric Recognition Studies of Novel C2-Symmetrical Chiral Tetra-Amide Compounds”, J. Inst. Sci. and Tech., vol. 11, no. 2, pp. 1293–1301, June 2021, doi: 10.21597/jist.802116.
ISNAD
Sünkür, Murat - Tiğiz, Züleyha - Cebe, Deniz - Aral, Tarık. “Synthesis and Enantiomeric Recognition Studies of Novel C2-Symmetrical Chiral Tetra-Amide Compounds”. Journal of the Institute of Science and Technology 11/2 (June 1, 2021): 1293-1301. https://doi.org/10.21597/jist.802116.
JAMA
1.Sünkür M, Tiğiz Z, Cebe D, Aral T. Synthesis and Enantiomeric Recognition Studies of Novel C2-Symmetrical Chiral Tetra-Amide Compounds. J. Inst. Sci. and Tech. 2021;11:1293–1301.
MLA
Sünkür, Murat, et al. “Synthesis and Enantiomeric Recognition Studies of Novel C2-Symmetrical Chiral Tetra-Amide Compounds”. Journal of the Institute of Science and Technology, vol. 11, no. 2, June 2021, pp. 1293-01, doi:10.21597/jist.802116.
Vancouver
1.Murat Sünkür, Züleyha Tiğiz, Deniz Cebe, Tarık Aral. Synthesis and Enantiomeric Recognition Studies of Novel C2-Symmetrical Chiral Tetra-Amide Compounds. J. Inst. Sci. and Tech. 2021 Jun. 1;11(2):1293-301. doi:10.21597/jist.802116