Conformational analysis of three germacranolides by the PM3 semi-empirical method
Konformaciona analiza tri germakranolida PM3 semi-empirijskom metodom
Apstrakt
The conformations of the C-6 lactomized germacranolides 1-3 were calculated by applying the PM3 semi-empirical method, The low-temperature H-1-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 die elucidation and prediction of die 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.
Ključne reči:
germacranolides / parthenolide / parthenolide / ridentin / ridentin / 1β,10α-epoxy-3β,9β-diacetoxy-11α,13-dihydrocostunolide / 1 beta / 10 alpha-epoxy-3 beta / conformations / PM3 semi-empirical calculations / 9 beta-dacetoxy-11 alpha / 13-di-hydrocosturiolide / conformations / PM3 serni-empirical calculationsIzvor:
Journal of the Serbian Chemical Society, 2003, 68, 4-5, 281-289Izdavač:
- Serbian Chemical Soc, Belgrade
DOI: 10.2298/JSC0305281M
ISSN: 0352-5139
WoS: 000183423800007
Scopus: 2-s2.0-0037498107
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Milosavljevic, S AU - Juranić, Ivan O. AU - Aljančić, Ivana AU - Vajs, Vlatka AU - Todorović, Nevena M. PY - 2003 UR - https://cherry.chem.bg.ac.rs/handle/123456789/554 AB - The conformations of the C-6 lactomized germacranolides 1-3 were calculated by applying the PM3 semi-empirical method, The low-temperature H-1-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 die elucidation and prediction of die 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 Soc, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Conformational 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 = "Milosavljevic, S and Juranić, Ivan O. and Aljančić, Ivana and Vajs, Vlatka and Todorović, Nevena M.", year = "2003", abstract = "The conformations of the C-6 lactomized germacranolides 1-3 were calculated by applying the PM3 semi-empirical method, The low-temperature H-1-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 die elucidation and prediction of die 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 Soc, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Conformational 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" }
Milosavljevic, S., Juranić, I. O., Aljančić, I., Vajs, V.,& Todorović, N. M.. (2003). Conformational analysis of three germacranolides by the PM3 semi-empirical method. in Journal of the Serbian Chemical Society Serbian Chemical Soc, Belgrade., 68(4-5), 281-289. https://doi.org/10.2298/JSC0305281M
Milosavljevic S, Juranić IO, Aljančić I, Vajs V, Todorović NM. Conformational 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 .
Milosavljevic, S, Juranić, Ivan O., Aljančić, Ivana, Vajs, Vlatka, Todorović, Nevena M., "Conformational 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 . .