Journal
JOURNAL OF MOLECULAR STRUCTURE
Volume 1054, Issue -, Pages 199-208Publisher
ELSEVIER
DOI: 10.1016/j.molstruc.2013.09.007
Keywords
4-Benzylpiperidine; Charge-transfer; Spectra; TCNQ; Thermal
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The reactions of the electron donor 4-benzylpiperidine (4BP) with the sigma-acceptor iodine and pi-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](+) I-3(-) [(4BP)(DDQ)(2)], and [(4BP)(TBCHD)] for the donor (4BP) and the acceptors I-2, 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 (K-CT), charge transfer energy (E-CT), molar extinction coefficients (epsilon(CT)), free energy change Delta G degrees and ionization potential I-P of the formed CT-complexes [(4BP)I](+) I-3(-) [(4BP)(DDQ)(2)] and [(4BP)(TBCHD)] were obtained. (C) 2013 Elsevier B.V. All rights reserved.
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