Nucleophilicity and solvent effects on the kinetics of 4-(pyren-1-yl)thiazol-2-amine interaction with 4,6-dinitrobenzofuroxan

Nizar El Guesmi, Essam M. Hussein, Basim H. Asghar, Rami J. Obaid, Rabab S. Jassas, Ahmed Alharbi, Hatem M. Altass, Ismail I. Althagafi, Moataz Morad, Ziad Moussa, Saleh A. Ahmed

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

A multistep synthesis of novel pyrene-based thiazole moiety been has been realized following some synthetic challenges and complications. The chemical structure of the synthesized compound has been established on the basis of both spectroscopic and analytical tools. Its nucleophilic reactivity with 4,6-dinitrobenzofuroxan (DNBF) has been successfully studied in solution. A kinetic study of the covalent electrophile/nucleophile combination of dinitrobenzofuroxan (DNBF, electrophile) and 4-(pyren-1-yl)thiazol-2-amine (nucleophile) resulting in the formation of the corresponding σ-adduct in solution is reported. The rate constant (k1) of the second-order relating to the C[sbnd]C bond forming step of this complexation process has been found to fit into the linear correlation log k = sN (N + E), thereby permitting the evaluation of the nucleophilicity parameter (N) of the 4-(pyren-1-yl)thiazol-2-amine. 4-(Pyren-1-yl)thiazol-2-amine has been subsequently ranked according to its reactivity profile on the general nucleophilicity scale developed recently by Mayr et al., leading to an interesting and direct comparison over a large domain of π-, σ-, and n-nucleophiles.

Original languageEnglish
Pages (from-to)3702-3713
Number of pages12
JournalArabian Journal of Chemistry
Volume13
Issue number2
DOIs
Publication statusPublished - Feb 2020

Keywords

  • Dinitrobenzofuroxan
  • Kinetic study
  • Nucleophilicity parameters
  • Pyrene-based heterocycles

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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