UV-Vis, IR spectra and thermal studies of charge transfer complexes formed in the reaction of 4-benzylpiperidine with σ- And π-electron acceptors

Adel Mostafa, Nada El-Ghossein, G. Benjamin Cieslinski, Hassan S. Bazzi

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The reactions of the electron donor 4-benzylpiperidine (4BP) with the σ-acceptor iodine and π-acceptors 7,7,8,8-tetracyanoquinodimethane (TCNQ), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), and 2,4,4,6-tetrabromo-2, 5-cyclohexadienone (TBCHD) were studied spectrophotometrically in chloroform at room temperature. The electronic and infrared spectra of the formed molecular charge-transfer (CT) complexes were recorded. Based on the obtained data, the charge-transfer complexes were formulated as [(4BP)I]+I3-, [(4BP)(DDQ)2], and [(4BP)(TBCHD)] for the donor (4BP) and the acceptors I2, DDQ and TBCHD. In the 4BP-TCNQ reaction, a short-lived CT complex is formed followed by rapid N-substitution by TCNQ forming the final reaction product 7,7,8-tricyano-8-benzylpiperidinylquinodimethane [TCBPQDM]. These products were isolated as solids and have been characterized through electronic and infrared spectra as well as elemental and thermal analysis measurements. The formation constants (KCT), charge transfer energy (ECT), molar extinction coefficients (εCT), free energy change ΔG° and ionization potential IP of the formed CT-complexes [(4BP)I]+I3-, [(4BP)(DDQ)2] and [(4BP)(TBCHD)] were obtained.

Original languageEnglish
Pages (from-to)199-208
Number of pages10
JournalJournal of Molecular Structure
Volume1054-1055
DOIs
Publication statusPublished - 2013

Fingerprint

Charge transfer
Electrons
Infrared radiation
Ionization potential
Chloroform
Reaction products
Iodine
Thermoanalysis
Free energy
Substitution reactions
Hot Temperature
cyclohexadienone
Chemical analysis
tetracyanoquinodimethane
Temperature

Keywords

  • 4-Benzylpiperidine
  • Charge-transfer
  • Spectra
  • TCNQ
  • Thermal

ASJC Scopus subject areas

  • Spectroscopy
  • Analytical Chemistry
  • Inorganic Chemistry
  • Organic Chemistry

Cite this

UV-Vis, IR spectra and thermal studies of charge transfer complexes formed in the reaction of 4-benzylpiperidine with σ- And π-electron acceptors. / Mostafa, Adel; El-Ghossein, Nada; Cieslinski, G. Benjamin; Bazzi, Hassan S.

In: Journal of Molecular Structure, Vol. 1054-1055, 2013, p. 199-208.

Research output: Contribution to journalArticle

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T1 - UV-Vis, IR spectra and thermal studies of charge transfer complexes formed in the reaction of 4-benzylpiperidine with σ- And π-electron acceptors

AU - Mostafa, Adel

AU - El-Ghossein, Nada

AU - Cieslinski, G. Benjamin

AU - Bazzi, Hassan S.

PY - 2013

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N2 - The reactions of the electron donor 4-benzylpiperidine (4BP) with the σ-acceptor iodine and π-acceptors 7,7,8,8-tetracyanoquinodimethane (TCNQ), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), and 2,4,4,6-tetrabromo-2, 5-cyclohexadienone (TBCHD) were studied spectrophotometrically in chloroform at room temperature. The electronic and infrared spectra of the formed molecular charge-transfer (CT) complexes were recorded. Based on the obtained data, the charge-transfer complexes were formulated as [(4BP)I]+I3-, [(4BP)(DDQ)2], and [(4BP)(TBCHD)] for the donor (4BP) and the acceptors I2, DDQ and TBCHD. In the 4BP-TCNQ reaction, a short-lived CT complex is formed followed by rapid N-substitution by TCNQ forming the final reaction product 7,7,8-tricyano-8-benzylpiperidinylquinodimethane [TCBPQDM]. These products were isolated as solids and have been characterized through electronic and infrared spectra as well as elemental and thermal analysis measurements. The formation constants (KCT), charge transfer energy (ECT), molar extinction coefficients (εCT), free energy change ΔG° and ionization potential IP of the formed CT-complexes [(4BP)I]+I3-, [(4BP)(DDQ)2] and [(4BP)(TBCHD)] were obtained.

AB - The reactions of the electron donor 4-benzylpiperidine (4BP) with the σ-acceptor iodine and π-acceptors 7,7,8,8-tetracyanoquinodimethane (TCNQ), 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), and 2,4,4,6-tetrabromo-2, 5-cyclohexadienone (TBCHD) were studied spectrophotometrically in chloroform at room temperature. The electronic and infrared spectra of the formed molecular charge-transfer (CT) complexes were recorded. Based on the obtained data, the charge-transfer complexes were formulated as [(4BP)I]+I3-, [(4BP)(DDQ)2], and [(4BP)(TBCHD)] for the donor (4BP) and the acceptors I2, DDQ and TBCHD. In the 4BP-TCNQ reaction, a short-lived CT complex is formed followed by rapid N-substitution by TCNQ forming the final reaction product 7,7,8-tricyano-8-benzylpiperidinylquinodimethane [TCBPQDM]. These products were isolated as solids and have been characterized through electronic and infrared spectra as well as elemental and thermal analysis measurements. The formation constants (KCT), charge transfer energy (ECT), molar extinction coefficients (εCT), free energy change ΔG° and ionization potential IP of the formed CT-complexes [(4BP)I]+I3-, [(4BP)(DDQ)2] and [(4BP)(TBCHD)] were obtained.

KW - 4-Benzylpiperidine

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KW - Spectra

KW - TCNQ

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