Theoretical calculation and structural studies for a new nitrogen derivative from nor-lapachol

•Synthesis of a new derivative of nor-lapachol.•X-ray crystallography of N-methyl-amine-nor-lapachol.•Theoretical calculations about the orbitals through DFT method.•Analysis of molecular electrostatic potential maps front the Hirschfeld surfaces. Nor-lapachol is a semi-synthetic naphthoquinone obta...

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Bibliographic Details
Published in:Journal of molecular structure 2014-02, Vol.1060, p.233-238
Main Authors: Santos, Jademilson Celestino dos, de França, José Adonias A., do Nascimento Aquino, Lucas E., Pereira, Mariano Alves, Mafud, Ana Carolina, Amorim Camara, Celso, Malta, Valéria R. Santos, Honório, Káthia Maria
Format: Article
Language:English
Subjects:
2-Methylamine-nor-lapachol
Computation
Crystallography
Derivatives
DFT
Hirschfeld surface
HOMO/LUMO
Mathematical analysis
Molecular structure
Similarity
Spectroscopy
X-ray crystallography
X-rays
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Summary:•Synthesis of a new derivative of nor-lapachol.•X-ray crystallography of N-methyl-amine-nor-lapachol.•Theoretical calculations about the orbitals through DFT method.•Analysis of molecular electrostatic potential maps front the Hirschfeld surfaces. Nor-lapachol is a semi-synthetic naphthoquinone obtained by oxidative degradation from natural lapachol. This compound and its derivatives have been investigated for its interesting biological properties. Several naphthoquinone derivatives have been synthesized and characterized using different physicochemical and computational techniques, as such DFT, MM, spectroscopy and X-ray crystallography. Here, the structure of 2-methylamine-3-(2-methyl-1-propenyl-1-yl)-1,4-naphthoquinone was determined by X-ray crystallography and the geometry was optimized using B3LYP functional along with the 6-31G(d) basis set, which was also used in all calculations. The obtained results were compared with the structure determined experimentally, and both structures showed high similarity. Besides, some molecular properties of this compound were also calculated by using DFT as well as Hirschfeld surface.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2013.12.047