The CT-complexes of chlorothiazide (n-donor) with picric acid, 3, 5-dinitrobenzoic acid (pi-acceptor) and iodine (sigma-acceptor) were investigated at different temperatures and solvents. These complexes were investigated in polar solvents (methanol, acetonitrile) and nonpolar solvents (dichloromethane and chloroform). The structures of the CT-complexes were studied by 1HNMR, infrared spectra and elemental analyses. The donation method was occurred from the lone pair of electron of nitrogen atom in chlorothiazide to pi- acceptors (n→ π*) and to sigma-acceptor (n–σ). Scanning electronic microscopy (SEM) shows images of chlorothiazide with 3,5-dinitrobenzoic acid, indicates that the produced complex is crystalline with a rod-like shape as the major crystals shapes. The molecular composition of the charge transfers complexes was 1:1 ratio (donor: acceptor) which determined by spectrophotometric titration. The extinction coefficient, εCT, the formation constant, KCT, transition dipole moment (μ), the oscillator strength (f), resonance energy (RN), ionization potential IP and transition energy (ECT) values of the complex were calculated.