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Computational Analysis of 1,2‐dialkynylpyrroles
Author(s) -
Bondoc Joshua,
Kerwin Sean
Publication year - 2018
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.2018.32.1_supplement.lb105
Subject(s) - diradical , singlet state , chemistry , computational chemistry , transition state , molecule , photochemistry , chemical physics , physics , atomic physics , catalysis , organic chemistry , excited state
Computational chemistry can be used to quickly predict the properties of molecules. We are interested in studying the potential of 1,2‐dialkynylpyrroles to undergo a thermal Bergan cyclization‐triggered rearrangement to reactive diradical intermediates that display cytotoxic activity. These diradical intermediates have garnered much interest in the scientific community as a potential tumor suppressing compound. In order to analyze these diradicals, a B3LYP hybrid functional with a 6–31G** basis set was used to predict the electronic energy of each intermediate and transition state in the reaction. The electronic energy values for each step in the reaction were used to construct an energy diagram that quantified the energy gap between the intermediates and transition states. The goal of this experiment was to create an analogue of a dialkynylpyrrole that maximized the energy gap between the diradical singlet and the Retro Bergman transition state, and minimized the energy gap between the diradical singlet and the diradical triplet. An analogue that produced a diradical with these properties would be long lived and reactive. This abstract is from the Experimental Biology 2018 Meeting. There is no full text article associated with this abstract published in The FASEB Journal .