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Magnetic response and its relation to the keto‐enol tautomerism of 3,3′‐(1,4‐phenylene)bis(pentane‐2,4‐dione): Experimental and theoretical insights
Author(s) -
Lancheros Andres,
Zarate Ximena,
Schott Eduardo
Publication year - 2020
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.26360
Subject(s) - tautomer , pentane , aromaticity , chemistry , enol , computational chemistry , phenylene , keto–enol tautomerism , thermodynamics , organic chemistry , molecule , physics , polymer , catalysis
A direct correlation between aromaticity and the thermodynamic stability in the tautomeric equilibrium of 3,3′‐(1,4‐phenylene)bis(pentane‐2,4‐dione) is studied using experimental methods and theoretical approaches. According to the results, the most abundant tautomer corresponds to the bis‐β‐keto‐enol tautomer when conditions such as temperature, solvent polarity, and pH are deliberately changed. Theoretical results of aromaticity analysis showed good concordance with the experimental results, using rigorous computations such as induced magnetic field ( B ind ) and free of in‐plane component NICS (FIPC‐NICS).