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Predominance of 2‐arylhydrazones of 1,3‐diphenylpropane‐1,2,3‐trione over its proton‐transfer products
Author(s) -
Gawinecki Ryszard,
Kolehmainen Erkki,
Janota Henryk,
Kauppinen Reijo,
Nissinen Maija,
Ośmiałowski Borys
Publication year - 2001
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.435
Subject(s) - tautomer , chemistry , substituent , chloroform , hydrazone , moiety , computational chemistry , ab initio , proton , chemical shift , ab initio quantum chemistry methods , medicinal chemistry , stereochemistry , organic chemistry , molecule , physics , quantum mechanics
2‐Phenylhydrazones of 1,3‐diphenyl‐1,2,3‐trione are the dominant tautomeric form detected in chloroform solution by 15 N NMR chemical shifts. The substituent in the phenylhydrazone moiety does not affect this tautomeric preference. The substituent effect is transmitted effectively only to the hydrazone nitrogen and hydrogen atoms. Ab initio calculations show that the ketohydrazone tautomer is really very much favoured over its proton‐transfer products in chloroform solution. The same tautomer was also detected in the crystal state by X‐ray crystallography. Copyright © 2001 John Wiley & Sons, Ltd.