Solvent Effects in the Nuclear Magnetic Resonance Spectra of Benzal Compounds

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Abstract:

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.

Keywords: Nuclear magnetic resonance of benzal compounds, solvent effects

Document Type: Research Article

DOI: http://dx.doi.org/10.1366/000370274774332669

Affiliations: 1: Defence Research Establishment Ottawa, Ontario, Canada; present address: Defence Research Analysis Establishment, Ottawa, Ontario, Canada 2: Defence Research Establishment Ottawa, Ontario, Canada 3: Defence Research Establishment Suffield, Ralston, Alberta, Canada

Publication date: March 1, 1974

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