Regiospecific nucleophilic substitution in 2,3,4,5,6-pentafluorobiphenyl as model compound for supramolecular systems. Theoretical study of transition states and energy profiles, evidence for tetrahedral SN2 mechanism

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22340%2F10%3A00023278" target="_blank" >RIV/60461373:22340/10:00023278 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22310/10:00023697

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Regiospecific nucleophilic substitution in 2,3,4,5,6-pentafluorobiphenyl as model compound for supramolecular systems. Theoretical study of transition states and energy profiles, evidence for tetrahedral SN2 mechanism

Popis výsledku v původním jazyce

2,3,4,5,6-Pentafluorobiphenyl (PFBi) was modified by the nucleophilic substitution of one fluorine using a series of O-, S- and N-nucleophiles, viz. alkaline salts of 2,2,2-trifluoro-ethanol, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanol, 1,2;3,4-di-O-isopropylidenexylitol, allylsulfane, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane-1-thiol, 3-aminopropan-1-ol (7), and tert-butyl N-(3-aminopropyl)carbamate (8). All the substitutions took place exclusively at the position para to the phenyl group. (3-Amino-propyl)amino derivative of PFBi (15) was further modified at the terminal amino group by acylation or fluoroalkylation. The reaction of 8 was applied to meso-5,10,15,20-tetrakis-(pentafluorophenyl)porphyrin (20) to afford tris- (21) and tetrakis-substituted (22) products with complete para-regioselectivity. Theoretical studies of the reaction pathways of PFBi with ammonia, microsolvated lithium fluoride or lithium hydroxide revealed that no Meisenheimer-type intermediates are formed

Název v anglickém jazyce

Regiospecific nucleophilic substitution in 2,3,4,5,6-pentafluorobiphenyl as model compound for supramolecular systems. Theoretical study of transition states and energy profiles, evidence for tetrahedral SN2 mechanism

Popis výsledku anglicky

2,3,4,5,6-Pentafluorobiphenyl (PFBi) was modified by the nucleophilic substitution of one fluorine using a series of O-, S- and N-nucleophiles, viz. alkaline salts of 2,2,2-trifluoro-ethanol, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanol, 1,2;3,4-di-O-isopropylidenexylitol, allylsulfane, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane-1-thiol, 3-aminopropan-1-ol (7), and tert-butyl N-(3-aminopropyl)carbamate (8). All the substitutions took place exclusively at the position para to the phenyl group. (3-Amino-propyl)amino derivative of PFBi (15) was further modified at the terminal amino group by acylation or fluoroalkylation. The reaction of 8 was applied to meso-5,10,15,20-tetrakis-(pentafluorophenyl)porphyrin (20) to afford tris- (21) and tetrakis-substituted (22) products with complete para-regioselectivity. Theoretical studies of the reaction pathways of PFBi with ammonia, microsolvated lithium fluoride or lithium hydroxide revealed that no Meisenheimer-type intermediates are formed

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CB - Analytická chemie, separace

OECD FORD obor

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Projekt

<a href="/cs/project/GA203%2F09%2F1311" target="_blank" >GA203/09/1311: Syntetické próby pro rozpornávání nádorových markerů: aplikace pro řízenou buněčnou apoptózu a směrovanou fotodynamickou terapii</a><br>

Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2010

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Fluorine Chemistry

ISSN

0022-1139

e-ISSN

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Svazek periodika

131

Číslo periodika v rámci svazku

12

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

11

Strana od-do

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Kód UT WoS článku

000285899700008

EID výsledku v databázi Scopus

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