NMR of Acetanilide

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


Introduction

The log files of my old web server indicated 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 or allows JavaScript, 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; DOI: 10.1021/j100044a009

H. J. Wasserman, R. R. Ryan, S. P. Layne,
"Structure of acetanilide (C8H9NO) at 113 K",
Acta Cryst. 1985, C41, 783. DOI: 10.1107/S0108270185005492

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. 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
H-1 NMR data on acetanilide
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.
S. Bienz, L. Bigler, T. Fox: Spektroskopische Methoden in der organischen Chemie, Georg Thieme Verlag, Stuttgart, 9th ed., 2016, p. 233; DOI: 10.1055/b-004-129729
[2]from a H-1 NMR spectrum shown by Stephen Jones;
the original URL does not exist anymore, but you can find a copy at the Internet Archive
Note that the aromatic protons may look like triplets and doublets, but they actually constitute an ABB'CC' spin system and should be analyzed as such!

 

C-13 NMR Spectrum of Acetanilide

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

CH3 [1]24.1
C-13 NMR data on acetanilide
ortho-C [1]120.4
para-C [1]124.1
meta-C [1]128.7
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.
S. Bienz, L. Bigler, T. Fox: Spektroskopische Methoden in der organischen Chemie, Georg Thieme Verlag, Stuttgart, 9th ed., 2016, p. 233; DOI: 10.1055/b-004-129729
[2]there is a C-13 NMR spectrum shown by Stephen Jones;
the original URL does not exist anymore, but you can find a copy at the Internet Archive

 

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:
https://doi.org/10.1021/es990288w

M. D. Morton, F. H. Walters, D. S. Aga, E. M. Thurman, and C. K. Larive:
Nuclear Magnetic Resonance Identification of New Sulfonic Acid Metabolites of
Chloroacetanilide Herbicides 
Journal of Agricultural and Food Chemistry, 1997, 45, 1240-1243: 
https://doi.org/10.1021/jf960453g

M.Barthes, M. Ribet 
"Compared 13C NMR spectra of Acetanilide and N-methylacetamide", 
Berichte der Bunsengesellschaft, 1997, 102(3), 419-421: 
https://doi.org/10.1002/bbpc.19981020321

M.Barthes, G.De Nunzio, M. Ribet,
"Polarons or proton transfer in chains of peptide groups", 
Synthetic Metals v.76,337, (1996):
https://doi.org/10.1016/0379-6779(95)03484-2

Johnson, M. R., Prager, M., Grimm, H., Neumann, M. A., Kearley, G. J. and Wilson, C. C.:
Methyl group dynamics in paracetamol and acetanilide: probing the static 
properties of intermolecular hydrogen bonds formed by peptide groups. 
Chemical Physics, 1999, vol. 244, 49-66:
https://doi.org/10.1016/S0301-0104(99)00138-X 

A. Bulai, A.-A. Alencar de Queiroz, A. Gallardo and J. San Roman:
Microstructural analysis of p-acryloyloxy-acetanilide and 
N,N-dimethylacrylamide copolymers of biomedical interest by NMR
POLYMER, VOL. 40 , NO. 17 , 1999, 4953  			
https://doi.org/10.1016/S0032-3861(98)00710-1