J. Bellanato, E. Gálvez, M. Espada
Oct 1, 1980
Citations
0
Influential Citations
9
Citations
Journal
Journal of Molecular Structure
Abstract
Abstract The IR spectra of 3-alkyl-3-azabicyclo(3.2.1)octane-8-spiro-, 3-alkyl-3-azabicyclo(3.3.1) nonane-9-spiro-, and 8-alkyl-8-azabicyclo(4.3.1)decane-10-spiro-5'-hydantoins have been studied in the solid state and in solution and the existence of different types of hydrogen bonding deduced from the spectra. The presence of intermolecular N3'-H⋯N bonds in the solid state depends mainly on the steric hindrance of the polymethylene chain and on the bulk and shape of the piperidine N-substituent. The possibility of strong N3'-H⋯N bond formation is smaller than for isomeric nortropane- and granatanine-spirohydantoins. Results are confirmed in some cases by Raman and X-ray measurements.