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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21 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 - Jan 2010

Fingerprint

Charge transfer
charge transfer
quinones
electronic spectra
Chloranil
infrared spectra
synthesis
Infrared radiation
Chlorine compounds
Iodine
chloroform
Reaction products
Stoichiometry
reaction products
Thermoanalysis
iodine
spectrum analysis
stoichiometry
thermal analysis
Substitution reactions

Keywords

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

ASJC Scopus subject areas

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

Cite this

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title = "Synthesis, spectroscopic and thermal structural investigations of the charge-transfer complexes formed in the reaction of 1-methylpiperidine with σ- and π-acceptors",
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.",
keywords = "1-Methylpiperidine (1MP), Charge-transfer, CHL, DDQ, Iodine (I), TCNE, TCNQ",
author = "Fakhroo, {Amina A.} and Bazzi, {Hassan S.} and Adel Mostafa and Lamis Shahada",
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TY - JOUR

T1 - Synthesis, spectroscopic and thermal structural investigations of the charge-transfer complexes formed in the reaction of 1-methylpiperidine with σ- and π-acceptors

AU - Fakhroo, Amina A.

AU - Bazzi, Hassan S.

AU - Mostafa, Adel

AU - Shahada, Lamis

PY - 2010/1

Y1 - 2010/1

N2 - 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.

AB - 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.

KW - 1-Methylpiperidine (1MP)

KW - Charge-transfer

KW - CHL

KW - DDQ

KW - Iodine (I)

KW - TCNE

KW - TCNQ

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JO - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

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