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Title: Dynamic 1H NMR study of rotational energy barrier around the aryl-nitrogen single bond in γ-spiroiminolactones derived from reaction between 2,6-dimethylphenyl isocyanide and dialkyl acetylenedicarboxylates in the presence of phendione
Authors: Maghsoodlou, Malek Taher
Marandi, Ghasem
Khorassani, Mostafa Habibi
Saghatforoush, Lotfali
Aminkhani, Ali
Kabiri, Roya
Keywords: Dynamic NMR
γ-spiroiminolactones
isocyanides
acetylenic esters
Issue Date: Jul-2008
Publisher: CSIR
Abstract: The Dynamic effects are observed in 1H NMR spectra of highly functional γ-spiroiminolactones such as dimethyl-5-(2,6-dimethylphenylimino)-6'-oxo-5H,6H'-spiro[furan-2,5'-[1,10]-phenanthroline]-3,4-dicarboxylate and di-tert-butyl-5-(2,6-dimethylphenylimino)-6'-oxo-5H, 6H'-spiro[furan-2, 5'-[1,10]phenanthroline]-3,4-dicarboxylate. The calculated free-energy of activation (ΔG) for restricted rotation around the aryl-nitrogen single bonds in γ-spiroiminolactones 4a and 4b amounts to (44.4 and 45.3)±2 kJ.mol-1 with first order rate constant (k=109.9 and 111.0 s-1) at appropriate temperature respectively.
Page(s): 1151-1153
ISSN: 0376-4699
Source:IJC-B Vol.47B(07) [July 2008]

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