Synthesis, spectroscopic and thermal structural investigations of the charge-transfer complexes formed in the reaction of 1-methylpiperidine with σ- and π-acceptors

Amina A. Fakhroo, Hassan S. Bazzi, Adel Mostafa, Lamis Shahada

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23 Citations (Scopus)

Abstract

The reactions of the electron donor 1-methylpiperidine (1MP) with the π-acceptors 7,7,8,8-tetracyanoquinodimethane (TCNQ), tetracyanoethylene (TCNE), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), 2,3,5,6-tetrachloro-1,4-benzoquinone (chloranil = CHL) and iodine (I2) were studied spectrophotometrically in chloroform at room temperature. The electronic and infrared spectra of the formed molecular charge-transfer (CT) complexes were recorded. The obtained results showed that the stoichiometries of the reactions are not fixed and depend on the nature of the acceptor. Based on the obtained data, the formed charge-transfer complexes were formulated as [(1MP)(TCNE)2], [(1MP)(DDQ)]·H2O, [(1MP)(CHL)] and [(1MP)I]I3, while in the case of 1MP-TCNQ reaction, a short-lived CT complex is formed followed by rapid N-substitution by TCNQ forming the final reaction products 7,7,8-tricyano-8-piperidinylquinodimethane (TCPQDM). The five solids products were isolated and have been characterized by electronic spectra, infrared spectra, elemental analysis and thermal analysis.

Original languageEnglish
Pages (from-to)134-141
Number of pages8
JournalSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume75
Issue number1
DOIs
Publication statusPublished - 1 Jan 2010

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Keywords

  • 1-Methylpiperidine (1MP)
  • CHL
  • Charge-transfer
  • DDQ
  • Iodine (I)
  • TCNE
  • TCNQ

ASJC Scopus subject areas

  • Analytical Chemistry
  • Atomic and Molecular Physics, and Optics
  • Instrumentation
  • Spectroscopy

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