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RESEARCH PRODUCT
Structural study of ethyl 3-arylcarbamoyl-2,3-diazabicyclo[2.2.1]hept-5-ene-2-carboxylates: conformation and transmission of substituent effects across the diazabicycloheptene ring
Maija NissinenErkki KolehmainenP. MeyerDusan LoosWolf-dieter RudorfKatri LaihiaAlexander PerjéssyJaakko KoivistoReijo Kauppinensubject
ChemistryStereochemistryOrganic ChemistrySubstituentElectronic structureRing (chemistry)CycloadditionNMR spectra databaseCrystallographychemistry.chemical_compoundNitrogen inversionPhysical and Theoretical ChemistryFourier transform infrared spectroscopyEne reactiondescription
Nine new ethyl 3-arylcarbamoyl-2,3-diazabicyclo[2.2.1]hept-5-ene-2-carboxylates were prepared by a [4 + 2] cycloaddition and their FTIR, 1H, 13C and 15N NMR spectra were measured and assigned. Single crystals were grown for five compounds and their X-ray data were obtained. The electronic structure and the conformations were calculated by the semi-empirical AM1 method. Using correlations between the spectral, empirical and theoretical structural data, the transmission of substituent effects and the preferential conformation connected with the consecutive double nitrogen inversion and regarding the mutual orientation of NH and CO bonds were investigated. The results are compared with those for a previously reported series of analogous ethyl 2-arylcarbamoyl-4,5-dimethyl-1,2,3,6-tetrahydropyridazine-1-carboxylates. Copyright © 2001 John Wiley & Sons, Ltd.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2001-11-01 | Journal of Physical Organic Chemistry |