Intramolecular Hydrogen Bonds in Amino Amides.

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Amino amides have been included in this study (projects P8053 and P9095 of the Austrian Science Foundation FWF) to give a deeper insight into the factors that govern the structure of amino acids. The idea was to compare three different C_3-systems:

 HO-CH_2-CH_2-CO-OH,
          H_2N-CH_2-CH_2-CO-OH,
          H_2N-CH_2-CH_2-CO-NH_2.

From the comparison of omega-amino and omega-hydroxy acids it is known that the intramolecular N···H-O(CO) hydrogen bond is stronger than the corresponding O···H-O(CO) H-bond, whereas the O-H···O=C interaction is stronger than its N-H···O=C counterpart in omega-amino acids. But how does this interaction in omega-amino amides compare, and how does the N···H-N(CO) interaction perform?

The next page is devoted to a summary of results for 3-aminopropionamide, followed by a comparison with beta-alanine. Each page contains several illustrative pictures of relevant conformers. Although most of the information is contained in the text, so that a text-only browser is basically sufficient, these pictures will help in understanding. Therefore, if your browser can load pictures, you might want to turn that option on. The bottom of each page provides links for forward and backward browsing and, in the center entry, an interface to the literature data base of the Institute of Physical and Theoretical Chemistry. Activation of this interface produces an up-to-date list of publications and theses that relate to the specific topic.
 


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Informations required by Austrian law (Offenlegung gem. §25 MedienG): Dr. Michael Ramek, Graz.