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NMR of Acetanilide

Contents: [ Introduction ] [ Structure ] [ H-1 NMR ] [ C-13 NMR ] [ Links ]

 

Introduction

The log files of this web server indicate that a lot of people come to my pages because they were searching for "NMR of acetanilide" or similar. They got directed to my list of publications because two of my papers dealt with solid-state NMR of acetanilide or N-methylacetanilide. I don't suppose that they found what they were looking for! Although I don't know what those people expected to find I have created this special "NMR of acetanilide" page as a service to the Web community. If this page shows what you wanted, or you were looking for something else, why don't you let me know?

Structure of Acetanilide

If your browser supports Java, you can view and manipulate a molecular view of acetanilide on my
Structure of Acetanilide page

The crystal structures of acetanilide have been published in:

S. Johnson, J. Eckert, M. Barthes, R. Mc Mullan,
"Crystal Structure of Acetanilide at 15K and 295K by neutron diffraction",
J. Phys. Chem. 1995, 99, 16253

H. J. Wasserman, R. R. Ryan, S. P. Layne,
"Structure of acetanilide (C8H9NO) at 113 K",
Acta Cryst. 1985, C41, 783.

You can download a file containing the coordinates from the Wasserman paper in either PDB or CIF format. If you don't have software to view structures, you may want to try some of the programs listed on my X-ray links page. Alternatively, you could also download the Chime plugin for your browser. Or visit my Structure of Acetanilide page mentioned above.

H-1 NMR Spectrum of Acetanilide

The following chemical shifts were reported [1,2] for the protons of acetanilide:

CH3 [1] 2.1
para-H [1] 7.0
meta-H [1] 7.2
ortho-H [1] 7.4
NH [2] ca. 8.75
[1] M. Hesse, H. Meier, B. Zeeh: Spektroskopische Methoden in der organischen Chemie, Georg Thieme Verlag, Stuttgart, 2nd ed., 1984, p. 263.
[2] from a H-1 NMR spectrum shown by Stephen Jones

 

C-13 NMR Spectrum of Acetanilide

The following chemical shifts were reported [1] for the carbons of acetanilide:

CH3 [1] 24.1
para-C [1] 124.1
meta-C [1] 128.7
ortho-C [1] 120.4
ipso-C [1] 138.2
CO [1] 169.5
[1] M. Hesse, H. Meier, B. Zeeh: Spektroskopische Methoden in der organischen Chemie, Georg Thieme Verlag, Stuttgart, 2nd ed., 1984, p. 263.
[2] there is a C-13 NMR spectrum shown by Stephen Jones

 

Links and References in Crude Form

NIST entry of physical properties

Aga, D.S., Rentsch, D., Hany, R. and Muller, S.R.: 
Sulfonic and Oxanilic Acid Metabolites of
Acetanilide Herbicides: Separation of Diastereomers and Enantiomers 
by Capillary Zone Electrophoresis and Identification by 1H NMR Spectroscopy
Environ. Sci. Technol. 1999, 33, 3462-3468:
http://pubs.acs.org/subscribe/journals/esthag/jtoc.cgi?esthag/33/19
Journal of Agricultural and Food Chemistry, 1997, 45, 1240-1243 
Nuclear Magnetic Resonance Identification of New Sulfonic Acid Metabolites of
Chloroacetanilide Herbicides 
M. D. Morton, F. H. Walters, D. S. Aga, E. M. Thurman, and C. K. Larive 
http://pubs.acs.org/subscribe/journals/jafcau/jtoc.cgi?jafcau/45/4
Hetero Nuclear Dipolar NMR Spectroscopy of Organic Molecules
Dipolar NMR
M.Barthes, M. Ribet 
"Compared 13C NMR spectra of Acetanilide and N-methylacetamide", 
Berichte der Bunsengesellschaft, sous presse (1997) 

M.Barthes, M. Ribet "Dynamics of crystallized peptide chains" in 
"Biological Macromolecular Dynamics", 
Proc. Workshop on Inelastic and Quasielastic Neutron Scattering in Biology,
ILL Grenoble 1996, Eds S.Cusack et al. Adenine Press (1997)
 
M.Barthes, G.De Nunzio, M. Ribet,
"Polarons or proton transfer in chains of peptide groups", 
Synthetic Metals v.76,337, (1996)
 
M.Barthes, 
"Nonlinear Excitations in Molecular Crystals with chains of peptide 
groups" Cours de l'Ecole des Houches, in "Nonlinear Excitations in Biomolecules" 
Ed. M. Peyrard, Springer and Ed. de Physique (1995)

Methyl group dynamics in paracetamol and acetanilide: probing the static 
properties of intermolecular hydrogen bonds formed by peptide groups. 
Johnson, M. R., Prager, M., Grimm, H., Neumann, M. A., Kearley, G. J. and Wilson, C. C.
Chemical Physics, 1999, vol. 244, 49-66 

POLYMER, VOL. 40 , NO. 17 , 1999			
4953 Microstructural analysis of p-acryloyloxy-
acetanilide and N,N-dimethylacrylamide
copolymers of biomedical interest by NMR
A. Bulai, A.-A. Alencar de Queiroz, A. Gallardo
and J. San Roman


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