Physical organic studies and dynamic covalent chemistry of picolyl heterocyclic amino aminals.

ABSTRACT: A dynamic covalent system of the picolyl heterocyclic amino aminals has been studied. The aminals are characterized as a metastable species and easily switch to other forms via external stimuli. The solvent, temperature, acid-base and substituent effects have been examined to evaluate the dynamic covalent system. The results reveal that a more polar solvent, a lower temperature, basic conditions and an electron-withdrawing moiety contribute to the stabilities of aminals. The existence of the n → π* interaction between acetonitrile and the C[double bond, length as m-dash]N moiety makes the N-pyrimidyl imine (4c and 4d) yield higher in CD₃CN. In a similar fashion, all aminals tend to convert to the corresponding hemiaminal ethers in a methanol environment. According

SUBMITTER: Ciou JM 

PROVIDER: S-EPMC9057465 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature