TY - JOUR
T1 - N.m.r. spectra of cyclic amines. II—Factors influencing the chemical shifts of α‐protons in aziridines
AU - Breuer, Eli
AU - Somekh, Lila
AU - Ringel, Israel
PY - 1977/6
Y1 - 1977/6
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84986840349&partnerID=8YFLogxK
U2 - 10.1002/mrc.1270090609
DO - 10.1002/mrc.1270090609
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AN - SCOPUS:84986840349
SN - 0030-4921
VL - 9
SP - 328
EP - 332
JO - Organic Magnetic Resonance
JF - Organic Magnetic Resonance
IS - 6
ER -