The preferred conformation of α-fluoroamides

X-Ray structures of two α-fluoroamide derivatives show the OC–C–F moiety tending towards a trans planar conformation, for which ab initio calculations suggest a deep (up to 8 kcal mol–1) potential minimum.

[1]  N. Craig,et al.  Contribution to the Study of the Gauche Effect. The Complete Structure of the Anti Rotamer of 1,2-Difluoroethane , 1997 .

[2]  J. Howard,et al.  How good is fluorine as a hydrogen bond acceptor , 1996 .

[3]  H. Senderowitz,et al.  Computation of O-C-F and N-C-F systems : ab-initio calculations and a MM2 parameterization study. Theory vs. experiment , 1993 .

[4]  W. Herrebout,et al.  Vibrational conformational analysis of methyl fluoroacetate and methyl difluoroacetate , 1993 .

[5]  H. V. Phan,et al.  Conformational stability, structural parameters, and vibrational frequencies from ab initio calculations on fluoroacetaldehyde , 1990 .

[6]  M. J. Harrison,et al.  Asymmetric synthesis of protected α-fluoroglycines , 1989 .

[7]  L. Curtiss,et al.  Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint , 1988 .

[8]  J. Rétey,et al.  The transformation of α-aminoacids into fluoroacids , 1982 .

[9]  G. Olah,et al.  Synthetic Methods and Reactions. Part 106. Suppression of anchimerically assisted rearrangement products in the synthesis of α‐fluorocarboxylic acids from α‐amino acids with 48:52 (w/w) hydrogen fluoride/pyridine [1] , 1981 .

[10]  G. A. Jeffrey,et al.  Neutron diffraction at 20 K and ab initio molecular-orbital studies of the structure of monofluoroacetamide , 1981 .

[11]  G. A. Jeffrey,et al.  Neutron diffraction at 23 K and ab initio molecular-orbital studies of the molecular structure of acetamide , 1980 .

[12]  R. Small,et al.  The Crystal and Molecular Structure of Monofluoroacetamide , 1962 .