Accession Number:

AD0781350

Title:

Solvent Effects in the Nuclear Magnetic Resonance Spectra of Benzal Compounds,

Descriptive Note:

Corporate Author:

DEFENCE RESEARCH ESTABLISHMENT OTTAWA (ONTARIO)

Report Date:

1973-09-17

Pagination or Media Count:

6.0

Abstract:

Nuclear magnetic resonance spectra of benzal compounds, Z-C6H4-CHCXY, 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 ZNO2, Cl, H, Me,OMe, NMe2 beta-nitrostyrenes, beta-alkyl-beta-nitrostyrenes, cinnamates, cyanocinnamates, malonates, acetoacetates, acetylacetones, and cyanocinnamides. The ambiguity in the assignments to the olefinic protons in the beta-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 beta-nitrostyrenes show the largest solvent shifts for the olefinic protons, and the reasons for the more marked effects at the beta-proton are discussed. Author

Subject Categories:

  • Organic Chemistry
  • Atomic and Molecular Physics and Spectroscopy

Distribution Statement:

APPROVED FOR PUBLIC RELEASE