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-systems:
HO-CH-CH-CO-OH,
HN-CH-CH-CO-OH,
HN-CH-CH-CO-NH.
From the comparison of -amino
and -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 -amino acids.
But how does this interaction in -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 -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.
-systems:
-CH
H
-amino
-alanine.
starting point of H-bond tour.
3-aminopropionamide.
Quantum Chemistry Group.