Nuclear magnetic resonance studies of (Z)- and (E)-3-amino-3-(p-substituted phenyl)propenenitriles

Abstract

¹³ C N.m.r. shifts of (Z)- and (E)-3-amino-3-(p-substituted phenyl)propenenitriles [p-XC₆H₄C(NH₂)= CHCN; X = NMe₂, OMe, Me, H, Cl, or CF₃] in (CD₃)₂SO are reported. Ethylenic and cyano carbon chemical shifts are compared with those of trans- and cis-cinnamonitriles. The effect of substituents on ¹³C shifts, and correlations with σ⁺ substituent constants and with ¹H and ¹³C experimental shifts are also discussed.