Molecular orbital study of the oxidation of steroidal phenols into quinols and epoxyquinols
Molekulsko-orbitalno proučavanje oksidacije fenola u hinole i epoksihinole
Apstrakt
The MO study showed that the radical oxidation of phenols into quinols occurs readily. Further radical oxidation (in the m-CPBA/(BzO)(2)/hv system) of quinols occurs through appropriate biradical species with an activation energy of 79.5 kJ/mol yielding syn-epoxyquinols. The stereochemical outcome presented in this study is in full agreement with the experimental results.
Molekulsko-orbitalnim proučavanjem potvrđeno je da lako dolazi do radikalske oksidacije fenola u odgovarajuće hinole. Daljom oksidacijom sistemom m-CPBA/(BzO)2/hν hinoli se preko biradikalskih reakcionih vrsta oksiduju u odgovarajuće epoksihinole. Izračunato je da aktivaciona energija ove reakcije iznosi 79.5 kJ/mol. Stereohemijske posledice naših izračunavanja su u potpunom skladu sa eksperimentalnim rezultatima.
Ključne reči:
steroids / phenols / phenols / quinols / quinols / epoxyquinols / epoxyquinols / oxidation MNDO-PM3 study / oxidation MNDO-PM3 studyIzvor:
Journal of the Serbian Chemical Society, 2000, 65, 7, 491-496Izdavač:
- Serbian Chemical Soc, Belgrade
DOI: 10.2298/JSC0007491M
ISSN: 0352-5139
WoS: 000088450600004
Scopus: 2-s2.0-0034392264
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Marković, Zoran AU - Šolaja, Bogdan A. AU - Milić, Dragana AU - Juranić, Ivan O. AU - Gasic, MJ PY - 2000 UR - https://cherry.chem.bg.ac.rs/handle/123456789/437 AB - The MO study showed that the radical oxidation of phenols into quinols occurs readily. Further radical oxidation (in the m-CPBA/(BzO)(2)/hv system) of quinols occurs through appropriate biradical species with an activation energy of 79.5 kJ/mol yielding syn-epoxyquinols. The stereochemical outcome presented in this study is in full agreement with the experimental results. AB - Molekulsko-orbitalnim proučavanjem potvrđeno je da lako dolazi do radikalske oksidacije fenola u odgovarajuće hinole. Daljom oksidacijom sistemom m-CPBA/(BzO)2/hν hinoli se preko biradikalskih reakcionih vrsta oksiduju u odgovarajuće epoksihinole. Izračunato je da aktivaciona energija ove reakcije iznosi 79.5 kJ/mol. Stereohemijske posledice naših izračunavanja su u potpunom skladu sa eksperimentalnim rezultatima. PB - Serbian Chemical Soc, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Molecular orbital study of the oxidation of steroidal phenols into quinols and epoxyquinols T1 - Molekulsko-orbitalno proučavanje oksidacije fenola u hinole i epoksihinole VL - 65 IS - 7 SP - 491 EP - 496 DO - 10.2298/JSC0007491M ER -
@article{ author = "Marković, Zoran and Šolaja, Bogdan A. and Milić, Dragana and Juranić, Ivan O. and Gasic, MJ", year = "2000", abstract = "The MO study showed that the radical oxidation of phenols into quinols occurs readily. Further radical oxidation (in the m-CPBA/(BzO)(2)/hv system) of quinols occurs through appropriate biradical species with an activation energy of 79.5 kJ/mol yielding syn-epoxyquinols. The stereochemical outcome presented in this study is in full agreement with the experimental results., Molekulsko-orbitalnim proučavanjem potvrđeno je da lako dolazi do radikalske oksidacije fenola u odgovarajuće hinole. Daljom oksidacijom sistemom m-CPBA/(BzO)2/hν hinoli se preko biradikalskih reakcionih vrsta oksiduju u odgovarajuće epoksihinole. Izračunato je da aktivaciona energija ove reakcije iznosi 79.5 kJ/mol. Stereohemijske posledice naših izračunavanja su u potpunom skladu sa eksperimentalnim rezultatima.", publisher = "Serbian Chemical Soc, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Molecular orbital study of the oxidation of steroidal phenols into quinols and epoxyquinols, Molekulsko-orbitalno proučavanje oksidacije fenola u hinole i epoksihinole", volume = "65", number = "7", pages = "491-496", doi = "10.2298/JSC0007491M" }
Marković, Z., Šolaja, B. A., Milić, D., Juranić, I. O.,& Gasic, M.. (2000). Molecular orbital study of the oxidation of steroidal phenols into quinols and epoxyquinols. in Journal of the Serbian Chemical Society Serbian Chemical Soc, Belgrade., 65(7), 491-496. https://doi.org/10.2298/JSC0007491M
Marković Z, Šolaja BA, Milić D, Juranić IO, Gasic M. Molecular orbital study of the oxidation of steroidal phenols into quinols and epoxyquinols. in Journal of the Serbian Chemical Society. 2000;65(7):491-496. doi:10.2298/JSC0007491M .
Marković, Zoran, Šolaja, Bogdan A., Milić, Dragana, Juranić, Ivan O., Gasic, MJ, "Molecular orbital study of the oxidation of steroidal phenols into quinols and epoxyquinols" in Journal of the Serbian Chemical Society, 65, no. 7 (2000):491-496, https://doi.org/10.2298/JSC0007491M . .