N-p-tolyl-5-oxo pyrrolidine-3-carboxylic acid (TOPCA) was synthesized by Michael addition-cyclo condensation. The molecular structure of TOPCA was optimized by B3LYP method with 6-311G(d, p) and aug-cc-pVDZ (Dunning) basis sets as well as CAM-B3LYP method with 6-311G(d, p) basis set. In addition, MEP, CHELPG and NBO analyses were carried out to understand the influence of hydrogen bonding interactions. The molecular structure of TOPCA is governed by intramolecular hydrogen bonding interactions (C-H center dot center dot center dot O) which influence charge transfer in TOPCA. The C-H center dot center dot center dot O interactions stimulate the emission property of TOPCA excited at 380 nm. Intramolecular H-bonding and charge transfer induce the second hyperpolarizability in TOPCA. (C) 2017 Elsevier B.V. All rights reserved.