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Ab initio SCF investigation of the intramolecular hydrogen bonding in ϵ‐aminohexanoic acid
Author(s) -
Ramek Michael
Publication year - 1994
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560520707
Subject(s) - intramolecular force , conformational isomerism , hydrogen bond , chemistry , ab initio , crystallography , potential energy surface , ab initio quantum chemistry methods , group (periodic table) , computational chemistry , stereochemistry , molecule , organic chemistry
Ab initio RHF results (geometry data and potential barriers) are reported for the 14 symmetry unique local minima in the potential energy surface of ϵ‐aminohexanoic acid, which contain an intramolecular N ⃛HO hydrogen bond. Comparison of characteristic data with those of the homologs with fewer carbon atoms shows that δ‐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 ϵ‐aminohexanoic acid: In four such conformers, it occurs in syn ‐ clinal orientation. © 1994 John Wiley & Sons, Inc.