Detail publikačního výsledku

On the Question of the Formation of Nitro-Functionalized 2,4-Pyrazole Analogs on the Basis of Nitrylimine Molecular Systems and 3,3,3-Trichloro-1-Nitroprop-1-Ene

Kula, Karolina; Lapczuk, Agnieszka; Sadowski, Mikolaj; Kras, Jowita; Zawadzinska, Karolina; Demchuk, Oleg M.; Gaurav, Gajendra Kumar; Wroblewska, Aneta; Jasinski, Radomir

Originální název

On the Question of the Formation of Nitro-Functionalized 2,4-Pyrazole Analogs on the Basis of Nitrylimine Molecular Systems and 3,3,3-Trichloro-1-Nitroprop-1-Ene

Anglický název

On the Question of the Formation of Nitro-Functionalized 2,4-Pyrazole Analogs on the Basis of Nitrylimine Molecular Systems and 3,3,3-Trichloro-1-Nitroprop-1-Ene

Druh

Článek WoS

Originální abstrakt

Experimental and theoretical studies on the reaction between (E)-3,3,3-trichloro-1-nitroprop-1-ene and N-(4-bromophenyl)-C-arylnitrylimine were performed. It was found that the title process unexpectedly led to 1-(4-bromophenyl)-3-phenyl-5-nitropyrazole instead of the expected Delta(2)-pyrazoline molecular system. This was the result of a unique CHCl3 elimination process. The observed mechanism of transformation was explained in the framework of the molecular electron density theory (MEDT). The theoretical results showed that both of the possible channels of [3 + 2] cycloaddition were favorable from a kinetic point of view, due to which the creation of 1-(4-bromophenyl)-3-aryl-4-tricholomethyl-5-nitro-Delta(2)-pyrazoline was more probable. On the other hand, according to the experimental data, the presented reactions occurred with full regioselectivity.

Anglický abstrakt

Experimental and theoretical studies on the reaction between (E)-3,3,3-trichloro-1-nitroprop-1-ene and N-(4-bromophenyl)-C-arylnitrylimine were performed. It was found that the title process unexpectedly led to 1-(4-bromophenyl)-3-phenyl-5-nitropyrazole instead of the expected Delta(2)-pyrazoline molecular system. This was the result of a unique CHCl3 elimination process. The observed mechanism of transformation was explained in the framework of the molecular electron density theory (MEDT). The theoretical results showed that both of the possible channels of [3 + 2] cycloaddition were favorable from a kinetic point of view, due to which the creation of 1-(4-bromophenyl)-3-aryl-4-tricholomethyl-5-nitro-Delta(2)-pyrazoline was more probable. On the other hand, according to the experimental data, the presented reactions occurred with full regioselectivity.

Klíčová slova

pyrazoline; pyrazole; nitrocompound; nitrylimine; cycloaddition reaction; molecular electron density theory; synthesis; 3+2 CYCLOADDITION REACTIONS; 1,3-DIPOLAR CYCLOADDITION; PYRAZOLINE DERIVATIVES; AZOMETHINE YLIDES; MECHANISM; REACTIVITY; INSECTICIDES; INDOXACARB; CHEMISTRY; QUANTUM

Klíčová slova v angličtině

pyrazoline; pyrazole; nitrocompound; nitrylimine; cycloaddition reaction; molecular electron density theory; synthesis; 3+2 CYCLOADDITION REACTIONS; 1,3-DIPOLAR CYCLOADDITION; PYRAZOLINE DERIVATIVES; AZOMETHINE YLIDES; MECHANISM; REACTIVITY; INSECTICIDES; INDOXACARB; CHEMISTRY; QUANTUM

Autoři

Kula, Karolina; Lapczuk, Agnieszka; Sadowski, Mikolaj; Kras, Jowita; Zawadzinska, Karolina; Demchuk, Oleg M.; Gaurav, Gajendra Kumar; Wroblewska, Aneta; Jasinski, Radomir

Rok RIV

2023

Vydáno

01.12.2022

Nakladatel

MDPI

Místo

ST ALBAN-ANLAGE 66, CH-4052 BASEL, SWITZERLAND

ISSN

1420-3049

Periodikum

MOLECULES

Svazek

23

Číslo

27

Stát

Švýcarská konfederace

Strany počet

10

URL

https://www.mdpi.com/1420-3049/27/23/8409

BibTex

@article{BUT182690,
  author="Kula, Karolina and Lapczuk, Agnieszka and Sadowski, Mikolaj and Kras, Jowita and Zawadzinska, Karolina and Demchuk, Oleg M. and Gaurav, Gajendra Kumar and Wroblewska, Aneta and Jasinski, Radomir",
  title="On the Question of the Formation of Nitro-Functionalized 2,4-Pyrazole Analogs on the Basis of Nitrylimine Molecular Systems and 3,3,3-Trichloro-1-Nitroprop-1-Ene",
  journal="MOLECULES",
  year="2022",
  volume="23",
  number="27",
  pages="10",
  doi="10.3390/molecules27238409",
  url="https://www.mdpi.com/1420-3049/27/23/8409"
}