Journals / Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi / 2021 / Cilt: 11 - Sayı: 2

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

Pages
1293–1301
Publication Date
2021-06-01
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

These receptor compounds exhibited strong complexation (with Ka up to 5787.23 M-1) and very good enantioselectivity (up to KaS/KaR= 13.98).

📌 3 Key Takeaways

🎯
Objective & Hypothesis: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.
📊
Key Findings & Data: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.
💡
Conclusion & Impact:These receptor compounds exhibited strong complexation (with Ka up to 5787.23 M-1) and very good enantioselectivity (up to KaS/KaR= 13.98).
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Enantiomeric recognitionon · chiral amide · C2-symmetrical amino acid esters

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).

Özet

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).

🔖

Cite This Article

SÜNKÜR, M., TİĞİZ, Z., CEBE, D., ARAL, T. (2021). Synthesis and Enantiomeric Recognition Studies of Novel C2-Symmetrical Chiral Tetra-Amide Compounds. Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi, Cilt: 11 - Sayı: 2, 1293–1301. https://ajindex.com/articles/256505

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (2)

  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 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 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 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 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 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 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 Demirtas HN, Bozkurt S, Durmaz M, Yilmaz M, Sirit A, 2009. Chiral calix[4]azacrowns for enantiomeric recognition of amino acid derivatives. Tetrahedron, 65(15):3014-3018. doi: 10.1016/j.tet.2009.01.087 Deniz P, Turgut Y, Toğrul M, Hoşgören H, 2011. Pyridine containing chiral macrocycles: synthesis and their enantiomeric recognition for amino acid derivatives. Tetrahedron, 67(34):6227-6232. doi: 10.1016/j.tet.2011.06.064 Diederich F, 1988. Compl