N.m.r. spectra of cyclic amines. II—Factors influencing the chemical shifts of α‐protons in aziridines

Eli Breuer*, Lila Somekh, Israel Ringel

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

Proton magnetic resonance spectra of trans and cis‐2,3‐diphenylaziridine (1 and 2) and their N‐ethyl derivatives 3 and 4 were measured in carbon tetrachloride, chloroform, and benzene‐d6 at low temperatures (1 and 3) and in dry conditions (1 and 2). On the basis of these results it was concluded that an N‐ethyl group exerts a shielding influence on a cis ring proton and a deshielding influence on a trans ring proton. From results obtained by measuring the 1H n.m.r. spectra of 1–4 in deuterochlorofom‐trifluoroacetic acid it was derived that the lone pair of the aziridine nitrogen exerts a shielding influence on cis related ring hydrogens. In most N‐alkylaziridines the effect of the N‐alkyl group predominates.

Original languageEnglish
Pages (from-to)328-332
Number of pages5
JournalOrganic Magnetic Resonance
Volume9
Issue number6
DOIs
StatePublished - Jun 1977

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