Abstract
Quantum mechanical calculations were carried out to study the molecular geometry and electronic structure of 2-amino-2-desoxyglucopyranose (AG) and the Nacetyl-, N-ethanoyl-, series of N-phthalimidoalkanoyl-AG. The total charge density, electrostatic potential, spatial distribution and positions of HOMO and LUMO of N-acyl-AGs with respect to their substitutes yield information on the reactivity of the molecules.
Highlights
2-Amino-2-desoxyglucopyranoses (AG) containing N-acyl functional group residues display unique chemical and biological behavior Experimentally, the structure of N- substituents on 2-amido-AG have been shown to significantly affect the reactivity of the glucopyranose skeleton
N-phthalimidoalkanoyl substitution leads to a smaller highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy gap than in case of N-alkanoyl moieties
Energy gap reduction is caused by the strong decrease of LUMO energies
Summary
2-Amino-2-desoxyglucopyranoses (AG) containing N-acyl functional group residues display unique chemical and biological behavior Experimentally, the structure of N- substituents on 2-amido-AG have been shown to significantly affect the reactivity of the glucopyranose skeleton. Abstract: Quantum mechanical calculations were carried out to study the molecular geometry and electronic structure of 2-amino-2-desoxyglucopyranose (AG) and the Nacetyl-, N-ethanoyl-, series of N-phthalimidoalkanoyl-AG. The total charge density, electrostatic potential, spatial distribution and positions of HOMO and LUMO of N-acylAGs with respect to their substitutes yield information on the reactivity of the molecules.
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