Accession Number : AD0679542

Title :   AN NMR STUDY OF THE SOLVENT EFFECTS ON THE N-H CHEMICAL SHIFTS OF AROMATIC AMINES, AMIDES, AND HYDRAZINES,

Descriptive Note : Technical rept. Mar 67-Jul 68,

Corporate Author : AIR FORCE MATERIALS LAB WRIGHT-PATTERSON AFB OHIO

Personal Author(s) : Lewis,Ronald G. ; Dyer,Daniel S.

Report Date : OCT 1968

Pagination or Media Count : 28

Abstract : A series of aromatic amines, acetamides, and hydrazines were studied by nuclear magnetic resonance (nmr) spectroscopy. This study concentrates on the chemical shifts of the protons on nitrogen, and how these chemical shifts are affected by solvent and ring substituent. The spectrum of each compound was taken in deuterochloroform, acetone, benzene, and hexadeuterodimethyl sulfoxide where solubility permitted. From these spectra, solvent shifts were obtained for each solvent with CDCl3 as the reference solvent. Also substituent shifts were obtained for pairs of compounds (unsubstituted vs. orthomethyl-substituted; aromatic amines, amides, and hydrazines). These shifts are discussed in terms of solvent: solute complex formation, bond angles about the nitrogen atom, electron density on the nitrogen atom, and steric hindrance to complex formation. The effects of an orthomethyl group on these chemical shifts are discussed in light of the steric requirements of the methyl group. Also the steric requirements of an orthomethyl group could play a large role in determining the mode and geometry of solvent: solute complex formations which affect the chemical shifts of the N-H proton(s). (Author)

Descriptors :   (*NUCLEAR MAGNETIC RESONANCE, *AMINES), AMIDES, ACETAMIDES, HYDRAZINE DERIVATIVES, SOLUTIONS(MIXTURES), BENZENE, ACETONES, CHLOROFORM, DEUTERIUM COMPOUNDS, COMPLEX COMPOUNDS, ELECTRON DENSITY, AROMATIC COMPOUNDS

Subject Categories : Organic Chemistry
      Physical Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE