Peculiarities of the three-dimensional structures of isomers of 1,2,5-trimethyl-4-amino(amido)piperidines from the 1H and 13C NMR spectra

The three-dimensional structures of seven 1,2,5-trimethyl-4-amino(amido)piperidines were studied by means of the 1H and 13C NMR spectra. The 3JHH values and the 13C chemical shifts indicate that the substituents in the piperidine ring of all of the 2c,5c,4r isomers have a 2e,4e,5a orientation, while those in the piperidine ring of all of the 2c,5t,4r isomers have a 2e,4e,5e orientation. The conformational change (as a result of ring conversion) 2e,4a,5e → 2a,4e,5a was observed for the 2t,5c,4r isomers on passing from the corresponding amine to the amide; this change is associated with striving of the more bulky amide substituent to become equatorially oriented. Retarded rotation about the C(4)-N bond was observed in the 2c,5t,4r isomer of the 4-(N-phenylbenzamido) derivative; this is explained by steric hindrance due to the 5e-CH3 group. © 1988 Plenum Publishing Corporation.

Publisher
Латвийский институт органического синтеза Латвийской академии наук / Springer New York Consultants Bureau
Number of issue
1
Language
English
Pages
45-48
Status
Published
Volume
24
Year
1988
Organizations
  • 1 Patrice Lumumba Peoples' Friendship University, Moscow, 117923, Russian Federation
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/1274/
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