Conformational and structural predictions of α-aminoadipic acid
Abstract
The conformational landscape and equilibrium structure of α-aminoadipic acid have been studied by means of computational quantum methods. A final set of 17 conformers with relative energies lower than 900 cm -1 (10.75 kJ/mol) has been obtained by MP2/6-311++G(d,p) calculations. The structure of α-aminoadipic acid is controlled by the possible interactions between the three polar functional groups, the carboxylic and α-amino groups and the δ carboxylic group. The most stable conformer presents a type II interaction (N -H⋯O -H) stabilized by an N-H⋯O --C ε hydrogen bond with a folded lateral chain. Complementary QTAIM, NCI and NBO calculations have been done in order to further characterize the non-covalent interactions which govern the structure and conformational panorama of α-aminoadipic acid. Conformational interconversion potential energy functions have been explored, and relative Gibbs energies predicted to estimate the equilibrium population of the conformers. Significant discrepancies in the conformational landscape stabilities were observed between the relative Gibbs and electronic energies.
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BibTeX
@article{espinaco2026conformational,
title = {{Conformational and structural predictions of α-aminoadipic acid}},
author = {María Adela Espinaco and Susana Blanco and Juan Carlos López and Alberto Macario},
journal = {Results in Chemistry},
year = {2026},
month = oct,
doi = {10.1016/j.rechem.2025.102558},
url = {https://hal.science/hal-05775640v1},
note = {CC BY-NC-ND 4.0},
}
RIS
TY - JOUR
TI - Conformational and structural predictions of α-aminoadipic acid
AU - María Adela Espinaco
AU - Susana Blanco
AU - Juan Carlos López
AU - Alberto Macario
PY - 2026
DA - 2026/10/02
JO - Results in Chemistry
DO - 10.1016/j.rechem.2025.102558
UR - https://hal.science/hal-05775640v1
AB - The conformational landscape and equilibrium structure of α-aminoadipic acid have been studied by means of computational quantum methods. A final set of 17 conformers with relative energies lower than 900 cm -1 (10.75 kJ/mol) has been obtained by MP2/6-311++G(d,p) calculations. The structure of α-aminoadipic acid is controlled by the possible interactions between the three polar functional groups, the carboxylic and α-amino groups and the δ carboxylic group. The most stable conformer presents a type II interaction (N -H⋯O -H) stabilized by an N-H⋯O --C ε hydrogen bond with a folded lateral chain. Complementary QTAIM, NCI and NBO calculations have been done in order to further characterize the non-covalent interactions which govern the structure and conformational panorama of α-aminoadipic acid. Conformational interconversion potential energy functions have been explored, and relative Gibbs energies predicted to estimate the equilibrium population of the conformers. Significant discrepancies in the conformational landscape stabilities were observed between the relative Gibbs and electronic energies.
SN - 2211-7156
ER -