Kaliks[4]arenlerin homokiral amit türevlerinin sentezi ve enantiyomerlerin tanınmasında kullanılması
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Dosyalar
Tarih
2007-10-19
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Selçuk Üniversitesi Fen Bilimleri Enstitüsü
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Bu çalışmada p-t-bütilkaliks[4]aren ve kaliks[4]aren'in kiral sekiz yeni amit türevi (5-8, 9-12); 5,11,17,23-tetra-ter-bütil-25,27 dietoksikarbonilmetoksi-26,28- dihidroksi kaliks[4] aren (3) ve 25,27 dietoksikarbonilmetoksi-26,28-dihidroksi kaliks[4] aren (4) ile 2- amino-1-butanol, fenil glisinol, 3-fenil-1-amino-propanol ve (1S,2S)-(+)-2-amino-1-(4-nitrofenil)-1,3-propandiol amino alkolleri tepkimeye sokularak elde edilmiştir. Kaliks[4]arenin kiral amit türevleri kiral aminlerin moleküler tanınma çalışmalarında ve amino asitlerin faz transfer ekstraksiyonunda kullanılmıştır. Ayrıca bu bileşiklerden 10 ve 12' nin feniletil amin ve 1,2-propandiol guestlerine karşı kiral tanınma özellikleri 1H NMR spektroskopisi kullanılarak incelenmiştir. Gerçekleştirilen tüm reaksiyonlar İTK ile izlenmiş ve elde edilen ürünler kolon kromatografisi ile saflaştırılarak yapıları IR ve 1H NMR, 13C NMR ve FAB MS teknikleriyle aydınlatıldıktan sonra kiral bileşiklerin optik çevirme açıları ölçülmüştür.
In this study, eight novel chiral amide derivatives of calix[4]arene and p-tert-calix[4]arene (5-8, 9-12) have been synthesized from the reaction of 5,11,17,23-tetra-ter-butyl-25,27 diethoxycarbonylmethoxy-26,28-dihydroxy calix[4] arene (3) ve 25,27 diethoxycarbonylmethoxy-26,28-dihydroxy calix[4] arene with 2- amino-1-butanol, phenyl glycinol, 3-phenyl-1-amino-propanol and (1S,2S)-(+)-2-amino-1-(4-nitrophenyl)-1,3-propanediol, respectively. Chiral amide derivatives of calix[4]arene and p-tert-calix[4]arene have been used for molecular recognition of chiral amines and also phase transfer extraction of some selected ?-amino acids. Moreover chiral recognition capability of 10 ve 12 compounds towards the guests; phenylethyl amine and 1,2-propanediol by 1H NMR spectroscopy was investigated. The reactions were monitored by TLC and pure compounds were obtained after crystallysation, column chromatography or both. The structures of synthesized compounds were identified by IR, 1H NMR 13C NMR ve FAB MS and optical rotation measurements were also included.
In this study, eight novel chiral amide derivatives of calix[4]arene and p-tert-calix[4]arene (5-8, 9-12) have been synthesized from the reaction of 5,11,17,23-tetra-ter-butyl-25,27 diethoxycarbonylmethoxy-26,28-dihydroxy calix[4] arene (3) ve 25,27 diethoxycarbonylmethoxy-26,28-dihydroxy calix[4] arene with 2- amino-1-butanol, phenyl glycinol, 3-phenyl-1-amino-propanol and (1S,2S)-(+)-2-amino-1-(4-nitrophenyl)-1,3-propanediol, respectively. Chiral amide derivatives of calix[4]arene and p-tert-calix[4]arene have been used for molecular recognition of chiral amines and also phase transfer extraction of some selected ?-amino acids. Moreover chiral recognition capability of 10 ve 12 compounds towards the guests; phenylethyl amine and 1,2-propanediol by 1H NMR spectroscopy was investigated. The reactions were monitored by TLC and pure compounds were obtained after crystallysation, column chromatography or both. The structures of synthesized compounds were identified by IR, 1H NMR 13C NMR ve FAB MS and optical rotation measurements were also included.
Açıklama
Anahtar Kelimeler
Enantiyomerik tanıma, Enantiomeric recognition, Kaliksarenler, Calixarenes, Homokiral amit, Homochiral amide
Kaynak
WoS Q Değeri
Scopus Q Değeri
Cilt
Sayı
Künye
Kocabaş, E. (2007). Kaliks[4]arenlerin homokiral amit türevlerinin sentezi ve enantiyomerlerin tanınmasında kullanılması. Selçuk Üniversitesi, Yayımlanmış doktora tezi, Konya.
