%0 Journal Article
%T Electronic structure and molecular properties of nitisinone and mesotrione in water.
%A Imrich R
%A Štofko J
%A Boča R
%A Rajnák C
%J J Mol Model
%V 29
%N 12
%D 2023 Nov 13
%M 37953387
%F 2.172
%R 10.1007/s00894-023-05780-5
%X <B>BACKGROUND: </B>Nitisinone is a medium-sized organic molecule that is used in treating hereditary tyrosinemia type 1 (HT-1). The structurally analogous mesotrione, however, is used as a pesticide/herbicide. What molecular properties are responsible for the similarity/dissimilarity of these molecules is investigated here. The solvent effect reduces the electron affinity to rather negative values and causes the negative electron affinity which manifests itself in a very high positive absolute reduction potential.<BR><B>METHODS: </B>B3LYP method was utilized for a geometry optimization of nitisinone and mesotrione in their neural and ionized (L0, L+, L-) forms of 6 structures. The calculations were conducted in water as a solvent using conductor-like polarizable continuum model (CPCM), nitisinone also in vacuo. The complete vibrational analysis at the true energy minimum allows evaluating the thermodynamic functions with focus to the zero-point energy and overall entropic term. The change of the Gibbs energy on reductions and/or oxidation facilitates evaluating the absolute reduction and absolute oxidation potentials. Also, DLPNO-CCSD(T) method that involves the major part of the correlation energy has been applied to nitisinone and mesotrione and their molecular ions.