Conformation analysis of three germacranolides by the PM3 semi-empirical method
Konformaciona analiza tri germakranolida PM3 semi-empirijskom metodom
Апстракт
The conformations of the C-6 lactonized germacranolides 1–3 were calculated by applying the PM3 semi-empirical method. The low-temperature 1H-NMR spectra of parthenolide (1) were also measured. The relations between the calculated and the experimentally determined geometries were established using a modified Karplus equation. The applied quantum-chemical calculations proved to be an efficient and easy-to-use tool for the elucidation and prediction of the properties of germacranolide-type sesquiterpene lactones.
Konformacije germakranolida 1–3, laktonizovanih u položaju (6), izračunate su primenom PM3 semi-empirijske MO metode. Takođe su snimljeni protonski NMR spektri partenolida (1) na niskim temperaturama. Pomoću modifikovane Karplusove jednačine je uspostavljena korelacija između eksperimentalno utvrđenih i izračunatih najstabilnijih konformacija. Zaključeno je da primenjena kvantno-hemijska izračunavanja brzo i pouzdano mogu predvideti i objasniti osobine seskviterpenskih laktona tipa germakranolida.
Кључне речи:
germacranolides / parthenolide / ridentin / 1β,10α-epoxy-3β,9β-diacetoxy-11α,13-dihydrocostunolide / conformations / PM3 semi-empirical calculationsИзвор:
Journal of the Serbian Chemical Society, 2003, 68, 4-5, 281-289Издавач:
- Serbian Chemical Society
DOI: 10.2298/JSC0305281M
ISSN: 0352-5139
WoS: 000183423800007
Scopus: 2-s2.0-0037498107
Институција/група
IHTMTY - JOUR AU - Milosavljević, Slobodan AU - Juranić, Ivan AU - Aljančić, Ivana AU - Vajs, Vlatka AU - Todorović, Nina PY - 2003 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/117 AB - The conformations of the C-6 lactonized germacranolides 1–3 were calculated by applying the PM3 semi-empirical method. The low-temperature 1H-NMR spectra of parthenolide (1) were also measured. The relations between the calculated and the experimentally determined geometries were established using a modified Karplus equation. The applied quantum-chemical calculations proved to be an efficient and easy-to-use tool for the elucidation and prediction of the properties of germacranolide-type sesquiterpene lactones. AB - Konformacije germakranolida 1–3, laktonizovanih u položaju (6), izračunate su primenom PM3 semi-empirijske MO metode. Takođe su snimljeni protonski NMR spektri partenolida (1) na niskim temperaturama. Pomoću modifikovane Karplusove jednačine je uspostavljena korelacija između eksperimentalno utvrđenih i izračunatih najstabilnijih konformacija. Zaključeno je da primenjena kvantno-hemijska izračunavanja brzo i pouzdano mogu predvideti i objasniti osobine seskviterpenskih laktona tipa germakranolida. PB - Serbian Chemical Society T2 - Journal of the Serbian Chemical Society T1 - Conformation analysis of three germacranolides by the PM3 semi-empirical method T1 - Konformaciona analiza tri germakranolida PM3 semi-empirijskom metodom VL - 68 IS - 4-5 SP - 281 EP - 289 DO - 10.2298/JSC0305281M ER -
@article{ author = "Milosavljević, Slobodan and Juranić, Ivan and Aljančić, Ivana and Vajs, Vlatka and Todorović, Nina", year = "2003", abstract = "The conformations of the C-6 lactonized germacranolides 1–3 were calculated by applying the PM3 semi-empirical method. The low-temperature 1H-NMR spectra of parthenolide (1) were also measured. The relations between the calculated and the experimentally determined geometries were established using a modified Karplus equation. The applied quantum-chemical calculations proved to be an efficient and easy-to-use tool for the elucidation and prediction of the properties of germacranolide-type sesquiterpene lactones., Konformacije germakranolida 1–3, laktonizovanih u položaju (6), izračunate su primenom PM3 semi-empirijske MO metode. Takođe su snimljeni protonski NMR spektri partenolida (1) na niskim temperaturama. Pomoću modifikovane Karplusove jednačine je uspostavljena korelacija između eksperimentalno utvrđenih i izračunatih najstabilnijih konformacija. Zaključeno je da primenjena kvantno-hemijska izračunavanja brzo i pouzdano mogu predvideti i objasniti osobine seskviterpenskih laktona tipa germakranolida.", publisher = "Serbian Chemical Society", journal = "Journal of the Serbian Chemical Society", title = "Conformation analysis of three germacranolides by the PM3 semi-empirical method, Konformaciona analiza tri germakranolida PM3 semi-empirijskom metodom", volume = "68", number = "4-5", pages = "281-289", doi = "10.2298/JSC0305281M" }
Milosavljević, S., Juranić, I., Aljančić, I., Vajs, V.,& Todorović, N.. (2003). Conformation analysis of three germacranolides by the PM3 semi-empirical method. in Journal of the Serbian Chemical Society Serbian Chemical Society., 68(4-5), 281-289. https://doi.org/10.2298/JSC0305281M
Milosavljević S, Juranić I, Aljančić I, Vajs V, Todorović N. Conformation analysis of three germacranolides by the PM3 semi-empirical method. in Journal of the Serbian Chemical Society. 2003;68(4-5):281-289. doi:10.2298/JSC0305281M .
Milosavljević, Slobodan, Juranić, Ivan, Aljančić, Ivana, Vajs, Vlatka, Todorović, Nina, "Conformation analysis of three germacranolides by the PM3 semi-empirical method" in Journal of the Serbian Chemical Society, 68, no. 4-5 (2003):281-289, https://doi.org/10.2298/JSC0305281M . .