Spironaphthoxazines belong to one of the most promising classes of organic photochromes. Their main applications include: optical data recording and storage and switches, smart materials, sensors, photocontrolled drug delivery, biosensors for diagnostics etc. Particularly in medical and related fields, stem from their high photostability, fast switching, and structural versatility. Spironaphthoxazines exist in two primary forms: Closed Spiro (SP) form: colorless and Open Photomerocyanine (MC) form: colored. Upon UV irradiation, temperature, solvent or other stimuli exposure, the spironapthoxazines convert from SP to MC through the cleavage of spiro C-O bond. This transformation changes their molecular properties, enabling specific interactions with other molecules. A series of new spironaphthoxazines have been synthesized and the present work propose the investigation of ten of the new structures. In this work, Density Functional Theory (DFT) calculations was used and the molecules was described in PW91 and 6-311G(d,p) basis sets, [3]. The optimized molecular structure and the energy of individual molecular orbitals were predicted for ten spironaphthoxazine derivatives. HOMO-LUMO analysis with corresponding quantum global chemical reactivity descriptors of the studied molecules was obtained to predict molecular stability and reactivity of the molecules. Also, by DFT the vibrational frequencies, thermodynamic properties, NMR Chemical Shifts of molecules were predicted and the minimum energy pathway between the two geometries of the SP and MC forms with identification of the geometry of the transition state form was calculated. The results obtained based on computations were compared and discussed in order to establish the beneficial traits of possible future applications.