Solvent Effects in the Nuclear Magnetic Resonance Spectra of Benzal Compounds
Nuclear magnetic resonance spectra of benzal compounds, Z—C6H4—CH=C(X)Y, have been determined in carbon tetrachloride, chloroform, acetone, and benzene solutions. Group X, trans to the ring, was one of NO2, COOEt, COCH3,
CONH2, the series comprising mostly para-substituted (Z=NO2, Cl, H, Me, OMe, NMe2) β-nitrostyrenes, β-alkyl-β-nitrostyrenes, cinnamates, cyanocinnamates, malonates, acetoacetates, acetylacetones, and cyanocinnamides. The ambiguity in the
assignments to the olefinic protons in the β-nitrostyrenes was resolved by studying deuterated compounds. The solvent shifts for the aromatic protons are shown to be additive, the olefinic side chains and the ring substituents making characteristic contributions. The solvent effect for
the aromatic protons ortho to the side chain is most affected by variation of the latter and, when large, may contribute to the effect at the olefinic protons. The β-nitrostyrenes show the largest solvent shifts for the olefinic protons, and the reasons for the more marked effects
at the β-proton are discussed.
Nuclear magnetic resonance of benzal compounds, solvent effects
Document Type: Research Article
Defence Research Establishment Ottawa, Ontario, Canada; present address: Defence Research Analysis Establishment, Ottawa, Ontario, Canada
Defence Research Establishment Ottawa, Ontario, Canada
Defence Research Establishment Suffield, Ralston, Alberta, Canada
Publication date: March 1, 1974
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