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Computational study of the synthesis of benzoin derivatives from benzil
Author(s) -
Topal Kevser Göçmen,
Unaleroglu Canan,
Aviyente Viktorya
Publication year - 2006
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.20879
Subject(s) - benzil , benzaldehyde , benzoin , chemistry , reactivity (psychology) , substituent , computational chemistry , yield (engineering) , quantum yield , polarizable continuum model , solvent effects , medicinal chemistry , organic chemistry , solvent , catalysis , thermodynamics , medicine , physics , alternative medicine , pathology , quantum mechanics , fluorescence
Benzil (1,2‐diphenylethane‐1,2‐dione) undergoes cyanide catalyzed condensation with benzaldehyde to yield O ‐benzoylated benzoin (2‐benzoyl‐1,2‐diphenylethanone). In this study, the experimentally suggested mechanism has been modeled with PM3 and verified with B3LYP. The effect of the substituent on the reaction yield has been rationalized by considering two benzil derivatives; 1,2‐bis(2‐chlorophenyl)ethane‐1,2‐dione and 1,2‐bis(2‐fluorophenyl)ethane‐1,2‐dione and three benzaldehyde derivatives; o ‐fluorobenzaldehyde, o ‐methylbenzaldehyde and 2‐pyridinecarboxaldehyde. The effect of the solvent has been modeled by using the isodensity‐surface polarizable continuum (IPCM) model. Reactivity descriptors have been used to justify the reactivity differences of the various substituents. © 2006 Wiley Periodicals, Inc. Int J Quantum Chem, 2006