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Isoxazolone Reactivity Explained by Computed Electronic Structure Analysis
Author(s) -
Bella Giovanni,
Santoro Antonio,
Cordaro Massimiliano,
Nicolò Francesco,
Bruno Giuseppe
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201900369
Subject(s) - chemistry , tautomer , moiety , basis set , computational chemistry , enol , molecule , double bond , bond length , reactivity (psychology) , ring (chemistry) , density functional theory , stereochemistry , organic chemistry , medicine , alternative medicine , catalysis , pathology
Summary of main observation and conclusion Isoxazol(2 H )‐5‐one was chosen as a model molecule to study the structural features (α, β angles and carbonyl bond length) regarding lactone moiety in the isoxazolone species by computational calculation. DFT method with B3LYP 6‐311++G(2df,2p) basis set was used to carry out the optimization on a series (A and B families) of isoxazolones suitably substituted on double bond. The same computational method assisted by default solvent model was performed to evaluate the energies related to the tautomeric equilibrium of isoxazol(2 H )‐5‐one and to the keto‐enol process (IRC). NPA (Natural Population Analysis) allowed us to understand how electron density is distributed on the heterocycle ring, highlighting reactive sites in chemical reactions and the possible interactions with biological targets.