M. Ramek,
Ab-initio SCF Investigation of the Intramolecular Hydrogen Bonding in epsilon-Aminohexanoic Acid,
Int. J. Quant. Chem.: Quant. Biol. Symp. 21, 79-93 (1994).

 


Publication abstract:

Ab initio RHF results (geometry data and potential barriers) are reported for the 14 symmetry unique local minima in the potential energy surface of epsilon-aminohexanoic acid, which contain an intramolecular N···H-O hydrogen bond. Comparison of characteristic data with those of the homologs with fewer carbon atoms shows that delta-aminopentanoic acid forms the most stable hydrogen bonds. In contrast to these homologs, the -COOH group is not limited to anti-periplanar orientation in the H-bonded conformers of epsilon-aminohexanoic acid: In four such conformers, it occurs in syn-clinal orientation.

Interactive viewing:

The following list contains links to all 14 RHF/4-31G optimized conformers, labeled by their absolute energy in Hartree. These links return the coordinates in alchemy format, intended for interactive viewing via RasMol. As a prerequisite, RasMol has to be installed and set up as a helper application of the WWW-browser, in a form similar to the following (which works for Netscape 3.x or 4.x running on a Unix platform; a more detailed description of configuration details can be found elsewhere).

MIME-Type: chemical/x-alc
Suffix: alc
Application: /...path.../rasmol -alchemy %s > /dev/null

Viewers that experience difficulties in recognizing two colored dots in the little graphic next to this paragraph should adjust the RasMol background color by using a command similar to the following, and experiment to find a suitable triple of numbers between 0 and 255.

Application: echo 'background [51,51,51]' | /...path.../rasmol -alchemy %s > /dev/null

Related links:


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