Unexpected keto-enol tautomerism in the cyclopyridinophane: Class direct and indirect proofs
Revista de Chimie, cilt.59, sa.10, ss.1077-1082, 2008 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 59 Sayı: 10
- Basım Tarihi: 2008
- Doi Numarası: 10.37358/rc.08.10.1973
- Dergi Adı: Revista de Chimie
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.1077-1082
- Anahtar Kelimeler: CETOBOX, Indolizine cyclophane, Monoylide, Tautomeric forms
- Orta Doğu Teknik Üniversitesi Adresli: Hayır
Özet
The paper presents the synthesis of cyclo (bis-paraquat p-phenylene p-phenylene-carbonyl) tetrakis (hexafluorophosphate), named 'CETOBOX', and the closely related structural determinations. This compound exists in three tautomeric forms. These forms were evidentiated by NMR-data (1H-NMR, TOCSY, COSY, NOESY), UV-Vis spectra coupled with pH measurements and by synthesis. As the 'CETOBOX' gives "in situ" only the corresponding monoylide, the synthesis of a new fluorescent indolizine cyclophane has been performed by a 3+2 cycloaddition. All structures of the new compounds presented herein have been established by NMR spectroscopy. Also, theoretical methods (MM3, AM1, AM1-COSMO and B88LYPDFT) have been used to determine the most stable conformer structures.