From CO2 to CS2: a theoretical investigation of the
cycloaddition to aziridines mediated by metal-free
porphyrin-based catalytic systems

J 2023

From CO2 to CS2: a theoretical investigation of the cycloaddition to aziridines mediated by metal-free porphyrin-based catalytic systems

DAMIANO, Caterina, Nicola PANZA, Jakub NAGY, Emma GALLO, Gabriele MANCA et. al.

Základní údaje

Originální název

From CO2 to CS2: a theoretical investigation of the cycloaddition to aziridines mediated by metal-free porphyrin-based catalytic systems

Autoři

DAMIANO, Caterina, Nicola PANZA, Jakub NAGY (703 Slovensko, domácí), Emma GALLO a Gabriele MANCA (garant)

Vydání

New Journal of Chemistry, Royal Society of Chemistry, 2023, 1144-0546

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10402 Inorganic and nuclear chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.300 v roce 2022

Kód RIV

RIV/00216224:14310/23:00130834

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1039/d2nj05479e

UT WoS

000921676600001

Klíčová slova anglicky

carbon disulfide; carbon dioxide; reactivity; organic compounds; computational analysis; metal-free binary; molecules

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 30. 1. 2024 20:47, Mgr. Pavla Foltynová, Ph.D.

Anotace

V originále

A detailed computational analysis of the synthesis of thiazolidine-2-thiones by CS2 insertion into three membered aziridine rings is here reported. DFT studies highlighted the feasibility of the atom-efficient process by employing either the metal-free binary TPPH2/TBACl system or bifunctional TPPH4Cl2 molecules as the catalytic species. Detailed investigations into the mechanism promoted by the TPPH2/TBACl system indicated, as in the analogous cycloaddition of CO2, the pivotal role of the adduct between TPPH2 and TBACl salts in the synthesis of both N-aryl and N-alkyl thiazolidine-2-thiones. The latter species can be also obtained by using the eco-compatible TPPH4Cl2 catalyst, which is able to simultaneously activate CS2 and aziridine molecules. The comparison of the overall energy gains of the reaction between aziridines and CS2 with respect to the same process involving CO2 revealed that the formation of thiazolidine-2-thiones is more favoured than the synthesis of oxazolidin-2-ones paving the way to develop efficient and eco-compatible synthesis of thiazolidine-2-thiones.

Návaznosti

MUNI/A/1421/2022, interní kód MU

Název: Vývoj metod a instrumentace pro analýzu biologicky významných látek 2023

Investor: Masarykova univerzita, Vývoj metod a instrumentace pro analýzu biologicky významných látek 2023

Citovat

DAMIANO, Caterina, Nicola PANZA, Jakub NAGY, Emma GALLO a Gabriele MANCA. From CO2 to CS2: a theoretical investigation of the cycloaddition to aziridines mediated by metal-free porphyrin-based catalytic systems. New Journal of Chemistry. Royal Society of Chemistry, 2023, roč. 47, č. 9, s. 4306-4312. ISSN 1144-0546. Dostupné z: https://dx.doi.org/10.1039/d2nj05479e.

@article{2285517,
   author = {Damiano, Caterina and Panza, Nicola and Nagy, Jakub and Gallo, Emma and Manca, Gabriele},
   article_number = {9},
   doi = {http://dx.doi.org/10.1039/d2nj05479e},
   keywords = {carbon disulfide; carbon dioxide; reactivity; organic compounds; computational analysis; metal-free binary; molecules},
   language = {eng},
   issn = {1144-0546},
   journal = {New Journal of Chemistry},
   title = {From CO2 to CS2: a theoretical investigation of the cycloaddition to aziridines mediated by metal-free porphyrin-based catalytic systems},
   url = {https://doi.org/10.1039/D2NJ05479E},
   volume = {47},
   year = {2023}
}

TY  - JOUR
ID  - 2285517
AU  - Damiano, Caterina - Panza, Nicola - Nagy, Jakub - Gallo, Emma - Manca, Gabriele
PY  - 2023
TI  - From CO2 to CS2: a theoretical investigation of the cycloaddition to aziridines mediated by metal-free porphyrin-based catalytic systems
JF  - New Journal of Chemistry
VL  - 47
IS  - 9
SP  - 4306-4312
EP  - 4306-4312
PB  - Royal Society of Chemistry
SN  - 11440546
KW  - carbon disulfide
KW  - carbon dioxide
KW  - reactivity
KW  - organic compounds
KW  - computational analysis
KW  - metal-free binary
KW  - molecules
UR  - https://doi.org/10.1039/D2NJ05479E
N2  - A detailed computational analysis of the synthesis of thiazolidine-2-thiones by CS2 insertion into three membered aziridine rings is here reported. DFT studies highlighted the feasibility of the atom-efficient process by employing either the metal-free binary TPPH2/TBACl system or bifunctional TPPH4Cl2 molecules as the catalytic species. Detailed investigations into the mechanism promoted by the TPPH2/TBACl system indicated, as in the analogous cycloaddition of CO2, the pivotal role of the adduct between TPPH2 and TBACl salts in the synthesis of both N-aryl and N-alkyl thiazolidine-2-thiones. The latter species can be also obtained by using the eco-compatible TPPH4Cl2 catalyst, which is able to simultaneously activate CS2 and aziridine molecules. The comparison of the overall energy gains of the reaction between aziridines and CS2 with respect to the same process involving CO2 revealed that the formation of thiazolidine-2-thiones is more favoured than the synthesis of oxazolidin-2-ones paving the way to develop efficient and eco-compatible synthesis of thiazolidine-2-thiones.
ER  -

DAMIANO, Caterina, Nicola PANZA, Jakub NAGY, Emma GALLO a Gabriele MANCA. From CO2 to CS2: a theoretical investigation of the cycloaddition to aziridines mediated by metal-free porphyrin-based catalytic systems. \textit{New Journal of Chemistry}. Royal Society of Chemistry, 2023, roč.~47, č.~9, s.~4306-4312. ISSN~1144-0546. Dostupné z: https://dx.doi.org/10.1039/d2nj05479e.

Podrobný výpis o publikaci