The molecular structure and properties of 1,4-diformylpiperazine (1,4-dfp, C6H10N2O2) were investigated by Fourier transform infrared (FT-IR) spectroscopy, Raman spectroscopy and density functional theory (DFT). The Becke-3-Lee-Yang-Parr (B3LYP) functional was used with the 6-31++G(d,p) basis set. Total energy distribution (TED) analysis of normal modes was performed to identify characteristic frequencies by the scaled quantum mechanical (SQM) method. Halogeno-analogs of 1,4-dfp were studied to understand the halogen effect. Computations were focused on five conformational isomers of the compounds in the gas phase and in solutions. The computed and experimental frequencies of the C = O stretching vibration of 1,4-dfp were correlated with the empirical solvent parameters such as the Kirkwood-Bauer-Magat (KBM) equation, the solvent acceptor number (AN), Swain parameters and linear solvation energy relationships (LSER). The electronic properties of the compounds were also examined. The findings from the present work may be useful to understand systems involving the halogens and conformational changes analogous to the compounds investigated.