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 - CHL
KW - Charge-transfer
KW - DDQ
KW - Iodine (I)
KW - TCNE
KW - TCNQ
UR - http://www.scopus.com/inward/record.url?scp=72649091519&partnerID=8YFLogxK
U2 - 10.1016/j.saa.2009.09.055
DO - 10.1016/j.saa.2009.09.055
M3 - Article
C2 - 19914125
AN - SCOPUS:72649091519
SN - 1386-1425
VL - 75
SP - 134
EP - 141
JO - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
JF - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
IS - 1
ER -