Roichatul Madinah, Febdian Rusydi, Rizka N. Fadilla, Vera Khoirunisa, Lusia S. P. Boli, Adhitya G. Saputro, Nur H. Hassan, Azizan Ahmad
Noncovalent interactions, such as dispersion, play a significant role in the stability of flexible molecules, such as curcumin. This study revealed the importance of dispersion correction in the structure and keto-enol tautomerization of curcumin, which has rarely been addressed in computational studies. We rigorously constructed all possible unique curcumin conformers in the enol and keto forms within the first-principles framework. Regardless of the different environments, we carefully explained the agreement between the computational geometry (in the gas phase) and the experimental measurement (in the polymorph) by using dispersion correction. The calculation results for the aqueous solution of conformational abundance, thermochemistry, and reaction kinetics support the experimental observations after considering the dispersion correction. The study also suggests a water-catalyzed mechanism for keto-enol tautomerization, where dispersion correction plays a role in decreasing the energy barrier and making the keto form thermochemically and kinetically favorable. Our results could be helpful in future computational studies to find a method for increasing the aqueous solubility of curcumin; hence, the potential of curcumin as a multifunctional medicine can be fully achieved. © 2023 The Authors. Published by American Chemical Society
Department of Chemical Sciences, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, Selangor, Bangi, 43600, Malaysia; Research Center for Quantum Engineering Design, Faculty of Science and Technology, Universitas Airlangga, Surabaya, 60115, Indonesia; Department of Physics, Faculty of Science and Technology, Universitas Airlangga, Surabaya, 60115, Indonesia; Department of Precision Engineering, Graduate School of Engineering, Osaka University, Osaka, 565-0871, Japan; Department of Engineering Physics, Institut Teknologi Sumatera, Jl. Terusan Ryacudu, Lampung Selatan, 35365, Indonesia; Advanced Functional Materials Research Group, Faculty of Industrial Technology, Institut Teknologi Bandung, Bandung, 40132, Indonesia; Physics Study Program, Faculty of Mathematics and Natural Sciences, Universitas Jendral Soedirman, Purwokerto, 53122, Indonesia
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