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Reactivity and stability of aromatic carbonyl compounds using density functional theory‐based local and global reactivity descriptors
Author(s) -
Roy R. K.,
Choho K.,
De Proft F.,
Geerlings P.
Publication year - 1999
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/(sici)1099-1395(199906)12:6<503::aid-poc149>3.0.co;2-2
Subject(s) - chemistry , reactivity (psychology) , intermolecular force , aromaticity , density functional theory , computational chemistry , acetaldehyde , molecule , organic chemistry , medicine , alternative medicine , pathology , ethanol
The reactivity of acetaldehyde and some aromatic aldehydes towards acid‐catalysed oxygen‐18 exchange reactions with H 2 O 18 was studied using the density functional theory (DFT)‐based reactivity descriptors local softness and local hardness. Local softness is used to predict the preferable reactive sites within a given molecule, whereas local hardness reproduces the experimental intermolecular reactivity trends. A new concept, intrinsic global hardness, obtained via filtering out the volume effect of the global softness, shows an excellent correlation with the degree of aromaticity of the compounds. Copyright © 1999 John Wiley & Sons, Ltd.