Title of article :
Ring Inversion in Two Sterically Hindered (Z,Z)-Cycloocta-1,3-dienes
Author/Authors :
Yavari, Issa tarbiat modares university - Chemistry Department, تهران, ايران , Sirouspour, Mehdi tarbiat modares university - Chemistry Department, تهران, ايران , Souri, Sanaz tarbiat modares university - Chemistry Department, تهران, ايران , Nasiri, Farough tarbiat modares university - Chemistry Department, تهران, ايران , Djahaniani, Hoorieh tarbiat modares university - Chemistry Department, تهران, ايران
Abstract :
The 1H and 13C NMR spectra of 3,4-dibenzoyl-5-(benzylamino)-7,7-dimethylcycloocta-2,4- diene-1-one and dimethyl 3-(benzylamino)-5,5-dimethyl-7-oxocycloocta-2,8-diene-1,2-dicarboxy- late, at room temperature, are consistent with slow ring inversion. The energetic barriers for ring inversion in these compounds were determined by dynamic 1H NMR spectroscopy to be 95 ± 2 and 88 ± 2 kJ mol-1, respectively. The crystal structure of 3,4-dibenzoyl-5-(benzylamino)-7,7- dimethylcycloocta-2,4-diene-1-one (C31H29NO3) belongs to P21(1)/n space group with cell dimensions of a = 16.230(3) A, b = 9.4025(16) A, c = 17.089(3) A, β = 114.675(4)o. This (Z,Z)- cycloocta-1,3-diene derivative crystallizes in monoclinic space group with Z = 4, the final R value is 0.0518 for 10816 reflections.
Keywords :
Dibenzoylacetylene , X , ray structure , Enaminone , Cycloocta , 1,3 , diene , Ring inversion , Dynamic NMR spectroscopy
Journal title :
Jordan Journal of Chemistry
Journal title :
Jordan Journal of Chemistry
