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Crystal Structures, Circular Dichroism Spectra and Absolute Configurations of Some L-Ascorbic Acid Derivatives


Wittine, Karlo; Gazivoda, Tatjana; Markuš, Marko; Mrvoš-Sermek, Draginja; Hergold-Brundić, Antonija; Cetina, Mario; Žiher, Dinko; Gabelica, Vesna; Mintas, Mladen; Raić-Malić, Silvana
Crystal Structures, Circular Dichroism Spectra and Absolute Configurations of Some L-Ascorbic Acid Derivatives // Journal of Molecular Structure, 687 (2004), 101-106 (međunarodna recenzija, članak, znanstveni)


Naslov
Crystal Structures, Circular Dichroism Spectra and Absolute Configurations of Some L-Ascorbic Acid Derivatives

Autori
Wittine, Karlo ; Gazivoda, Tatjana ; Markuš, Marko ; Mrvoš-Sermek, Draginja ; Hergold-Brundić, Antonija ; Cetina, Mario ; Žiher, Dinko ; Gabelica, Vesna ; Mintas, Mladen ; Raić-Malić, Silvana

Izvornik
Journal of Molecular Structure (0022-2860) 687 (2004); 101-106

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
L-ascorbic acid derivatives; Single crystal X-ray diffraction; Circular dichroism spectroscopy; Cotton effect

Sažetak
Chiral 2, 3-O, O-dibenzyl ethers of L-ascorbic acid with 4-(5, 6-epoxy)- (4) and 6-O-tosyl- (8) functional groups were studied by X-ray crystallography and circular dichroism (CD) spectroscopy. The stereostructure of 2, 3-O, O-dibenzyl-5, 6-isopropylidene-L-ascorbic acid (6) and 8 was determined by X-ray crystal structure analysis. Comparison of the CD-spectra of 4 and 8 with the CD-spectra of their synthetic precursors (2-3, 5-7) and L-ascorbic acid (1) itself, as well as crystal structures of 6 and 8 permitted to deduce the absolute configuration of 4. Thus, the chiral atoms C-4 and C-5 in 4 have R- and S- configurations, which is consistent with the configuration of 1.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus