The results show that simple structured and easily accessible acyclic $C_2$-symmetrical compounds can also be used for enantiomeric recognition of racemic amino acids and mandelic acid in addition to complex molecules such as crown ethers and other cyclic molecules.
📌 3 Maddede Bu Makale
🎯
Amaç & Hipotez:Two novel $C_2$ -symmetric chiral diamines containing $alpha$ -phenylethyl and $alpha$-(1-naphthyl)ethyl chiral subunits were prepared with quantitative yields.
📊
Temel Bulgular & Veri:Enantiomeric recognition properties of these simple structured diamine ligands towards D- and L-amino acid esters and D- and L-mandelic acid were examined by the 1H NMR titration method.
💡
Sonuç & Katkı:The results show that simple structured and easily accessible acyclic $C_2$-symmetrical compounds can also be used for enantiomeric recognition of racemic amino acids and mandelic acid in addition to complex molecules such as crown ethers and other cyclic molecules.
🔬Tür:Araştırma Makalesi
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:Alan Parametreleri
Abstract
Two novel $C_2$ -symmetric chiral diamines containing $alpha$ -phenylethyl and $alpha$-(1-naphthyl)ethyl chiral subunits were prepared with quantitative yields. Enantiomeric recognition properties of these simple structured diamine ligands towards D- and L-amino acid esters and D- and L-mandelic acid were examined by the 1H NMR titration method. These ligands exhibited strong complexation (with $K_f$ up to 2481 $M^{-1}$) and good enantioselectivity (up to $K_L$ /$K_D$ = 4.08) towards the mandelic acid enantiomers. The results show that simple structured and easily accessible acyclic $C_2$-symmetrical compounds can also be used for enantiomeric recognition of racemic amino acids and mandelic acid in addition to complex molecules such as crown ethers and other cyclic molecules.
🔖
Bu Makaleye Atıf Yap
ARAL, H., ARAL, T. K., OLAK, M. C., GULLARI, B. Z., GULLARI, R. Z. (2022). $C_2$-symmetric chiral diamine ligands for enantiomeric recognition of amino acid esters and mandelic acid by proton NMR titration method. Turkish Journal of Chemistry, Cilt: 37 - Sayı: 3, 374–382. https://ajindex.com/articles/595334
Jinno, K. Ed. Chromatographic Separations Based on Molecular Recognition, VCH: Weinheim, 1996
Marchi-Artzner, V.; Artzner, F.; Karthaus, O.; Shimomura, M.; Ariga, K.; Kunitake, T.; Lehn, J. M. Langmuir 1998, 14, 5164{5171
Bohanon, T. M.; Caruso, P. L.; Denzinger, S.; Fink, R.; Mobius, D.; Paulus, W.; Preece, J. A.; Ringsdorf, H.; Schollmeyer, D. Langmuir 1999, 15, 174{184
Pu, L. Chem. Rev. 2004, 104, 1687{1716
Hembury, G. A.; Borovkov, V. V.; Inoue, Y. Chem. Rev. 2008, 108, 1{73
Lehn, J. M. Supramolecular Chemistry: Concepts and Perspectives, VCH: Weinheim, 1995
Chadwick, D. J.; Cli e, I. A.; Sutherland, I. O. J. Chem. Soc., Perkin. Trans. 1 1984, 1707{1717
Köylü, M. Z.; Aral, T.; Karakaplan, M.; Kocakaya, S. O.; Hosgoren, H. Turk. J. Chem. 2011, 35, 171{179
Demirtas, H. N.; Bozkurt, S.; Durmaz, M.; Yilmaz, M.; Sirit, A. Tetrahedron 2009, 65, 3014{3018
Fitzmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 6, 841{864
Diederich, F. Angew. Chem., Int. Ed. Engl. 1988, 27, 362{386
Aral, T.; Karakaplan, M. Tetrahedron Asymm. 2005, 16, 2119{2124
Aydn, I.; Aral, T.; Karakaplan, M.; Hosgoren, H. Tetrahedron Asymm. 2009, 20, 179{183
Kizirian, J. C.; Caille, J. C.; Alexakis, A. Tetrahedron Lett. 2003, 44, 8893{8895