TY - JOUR
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
Y1 - 2013
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
KW - Charge-transfer
KW - Spectra
KW - TCNQ
KW - Thermal
UR - http://www.scopus.com/inward/record.url?scp=84885511185&partnerID=8YFLogxK
U2 - 10.1016/j.molstruc.2013.09.007
DO - 10.1016/j.molstruc.2013.09.007
M3 - Article
AN - SCOPUS:84885511185
SN - 0022-2860
VL - 1054-1055
SP - 199
EP - 208
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
ER -