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An Analysis of 1 H, 13 C and 15 N NMR Substituent Chemical Shifts in para ‐ and meta ‐Substituted ( Z )‐Phenylhydrazones of 3‐Benzoyl‐5‐phenyl‐1,2,4‐oxadiazole
Author(s) -
Mezzina Elisabetta,
Spinelli Domenico,
Lamartina Liliana,
Buscemi Silvestre,
Frenna Vincenzo,
Macaluso Gabriella
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(20021)2002:1<203::aid-ejoc203>3.0.co;2-n
Subject(s) - chemistry , substituent , electrophile , moiety , chemical shift , aryl , nucleophile , carbon 13 nmr , stereochemistry , computational chemistry , medicinal chemistry , organic chemistry , catalysis , alkyl
The 1 H, 13 C and 15 N chemical shifts of the title compounds have been measured in CDCl 3 solutions. The data obtained allowed a map of the ground‐state electronic distribution in such ( Z )‐arylhydrazones to be sketched, indicating to what extent the substituent in the aryl component of the arylhydrazono moiety affects the electronic density at the key atoms involved in the mononuclear heterocyclic rearrangements (MHR) characteristic of these substrates: the hydrogen atom bound to N α (which affects the nucleophilic character of N α ), N‐2 (which affects the electrophilic character of N‐2 itself) and C‐5 (which affects the nucleofugacity of the N‐4/C‐5/O‐1 system).