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Pregled bibliografske jedinice broj: 46467

Enantiomerization of 3-Carbethoxy-1, 4-benzodiazepin-2-one ; Combined Chiral HPLC and Spectroscopic Study


Abatangelo, Anna; Zanetti, Flavio; Navarini, Luciano; Kontrec, Darko; Vinković, Vladimir; Šunjić, Vitomir
Enantiomerization of 3-Carbethoxy-1, 4-benzodiazepin-2-one ; Combined Chiral HPLC and Spectroscopic Study // Chirality, 14 (2002), 1; 12-17 (međunarodna recenzija, članak, znanstveni)


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Naslov
Enantiomerization of 3-Carbethoxy-1, 4-benzodiazepin-2-one ; Combined Chiral HPLC and Spectroscopic Study

Autori
Abatangelo, Anna ; Zanetti, Flavio ; Navarini, Luciano ; Kontrec, Darko ; Vinković, Vladimir ; Šunjić, Vitomir

Izvornik
Chirality (0899-0042) 14 (2002), 1; 12-17

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

Ključne riječi
Chiral selector; Silica-bound brush-type; Configurational stability; 1; 4-benzodiazepines

Sažetak
Recently developed chiral HPLC columns CHIRIS AD1 and CHIRIS AD2 have been demonstrated to separate racemic, configurationally unstable ethyl-7-chloro-2-oxo-5-phenyl-2, 3-dihydro-1H-1, 4-benzodiazepine-3-carboxylate (1) and its 3-methyl congener 2 ; fast on-column enantiomerization of configurationally unstable 1 was observed, however. Addition of 0.1% of AcOH to the eluting mixture inhibits enantiomerization, whereas the same percentage of Et3N completely precludes enantioseparation, suggesting base-catalysis by free beta -aminoethyl groups, present in low percentage in chiral stationary phase (CSP). When both CSPs were prepared under conditions of nonexhaustive acylation by N-DNB-alpha -aminoacids, no separation of 1 was observed. The rate of enantiomerization on CHIRIS AD2 was determined at 25 degreesC, the mechanism is discussed, and experimental results correlated with calculated relative stabilities of the tautomers la-c. Absolute (3S) configuration of (+) enantiomers of 1 and 2 was determined by comparison of their eluation profile to that of (+/-)-3 and (3S)-(+)-3, taking into account relative (psia or psie) configuration of the prevailing conformer in solution.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
0098050 - 0098050 (, )
0098051 - 0098051 (, )
00980701 - 00980701 (, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Profili:

Avatar Url Vitomir Šunjić (autor)

Avatar Url Vladimir Vinković (autor)

Avatar Url Darko Kontrec (autor)

Citiraj ovu publikaciju

Abatangelo, Anna; Zanetti, Flavio; Navarini, Luciano; Kontrec, Darko; Vinković, Vladimir; Šunjić, Vitomir
Enantiomerization of 3-Carbethoxy-1, 4-benzodiazepin-2-one ; Combined Chiral HPLC and Spectroscopic Study // Chirality, 14 (2002), 1; 12-17 (međunarodna recenzija, članak, znanstveni)
Abatangelo, A., Zanetti, F., Navarini, L., Kontrec, D., Vinković, V. & Šunjić, V. (2002) Enantiomerization of 3-Carbethoxy-1, 4-benzodiazepin-2-one ; Combined Chiral HPLC and Spectroscopic Study. Chirality, 14 (1), 12-17.
@article{article, year = {2002}, pages = {12-17}, keywords = {Chiral selector, Silica-bound brush-type, Configurational stability, 1, 4-benzodiazepines}, journal = {Chirality}, volume = {14}, number = {1}, issn = {0899-0042}, title = {Enantiomerization of 3-Carbethoxy-1, 4-benzodiazepin-2-one ; Combined Chiral HPLC and Spectroscopic Study}, keyword = {Chiral selector, Silica-bound brush-type, Configurational stability, 1, 4-benzodiazepines} }

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
  • MEDLINE





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