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Reactivity and structure of derivatives of 2‐hydroxy‐1,4‐naphthoquinone (lawsone)
Author(s) -
Lamoureux G.,
Perez Alice L.,
Araya Mario,
Agüero Christian
Publication year - 2008
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1435
Subject(s) - lawsone , chemistry , naphthoquinone , reactivity (psychology) , nucleophile , density functional theory , conjugate , computational chemistry , juglone , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , medicine , mathematical analysis , alternative medicine , mathematics , pathology
Abstract The structures of two derivatives of 2‐hydroxy‐1,4‐naphthoquinone (lawsone) are examined using the density functional theory (DFT) hybrid functional B3LYP. Using the optimized structure of lawsone acetate, the reactivity of acyl transfer is described. Also, the nucleophilicity of the conjugate base of lawsone is predicted using the conceptual descriptors related to softness within the DFT framework. Copyright © 2008 John Wiley & Sons, Ltd.