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Synthesis and structural study of 2′‐ and 2′,6′‐positioned methyl‐ and nitro‐substituted 3‐(arylhydrazono)pentane‐2,4‐diones
Author(s) -
Marten Jan,
Seichter Wilhelm,
Weber Edwin,
Böhme Uwe
Publication year - 2007
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.1225
Subject(s) - chemistry , pentane , ring (chemistry) , nitro , molecule , hydrogen bond , computational chemistry , quantum chemistry , crystal structure , quantum chemical , molecular geometry , crystallography , stereochemistry , organic chemistry , supramolecular chemistry , alkyl
A systematic series of ortho ‐methyl‐ and nitro‐substituted arylhydrazones 2–6 formed by Japp–Klingemann reaction between pentane‐2,4‐dione and the respective aryldiazonium salts have been synthesized and studied by X‐ray crystal structure analysis, with added quantum chemical calculations. The optimized molecular geometries based on DFT calculations, enabling determination of relevant rotational barriers, and the calculated bond and ring critical points, using the method of ‘atoms in molecules’, were found to correspond with the experimental data, involving specific molecular conformations and hydrogen‐bonded ring structure dependent on the ortho ‐substitution, thus making possible reliable structural prediction of this compound class. Copyright © 2007 John Wiley & Sons, Ltd.