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Density functional theory study of the electronic properties of naphthofuranquinone compounds with antitrypanocidal activity
Author(s) -
Manzoni V.,
Lyra M. L.,
Cavada B. S.,
Neto N. Saker,
Freire V. N.
Publication year - 2011
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.22557
Subject(s) - density functional theory , chemistry , molecule , computational chemistry , electronic structure , dipole , charge density , chemical physics , organic chemistry , physics , quantum mechanics
We perform a first‐principles calculation of the electronic properties of three recently synthesized naphtofuranquinone compounds that have an enhanced biological activity against the protozoan Trypanosoma cruzi that causes the Chagas disease. Using density functional theory, we show that the most active iodinized molecules have three stable conformations associated with the torsion angle of the iodine radical. For each stable conformation of these molecules, we compute the charge distribution, absorption electronic energy, and NMR‐shielding in the gas phase as well as in the presence of distinct solvent media. Our results show that the most active compound has a larger dipole moment and electronic absorption energy. The estimated chemical shifts are in good agreement with experimental findings, except for the carbon bonded to the Iodine atom. We discuss on potential improvements of the calculation prescription that can potentially overcome this point. © 2010 Wiley Periodicals, Inc. Int J Quantum Chem, 2010