dihydroxyacetone results summary

The electrostatic charges on the atoms of dihydroxyacetone . A negative charge is red, a positive charge is blue and white atoms have no electric charge.
Atom Number Charge (Atomic Units)
O 1 -0.64740
C 2 0.35830
C 3 0.59310
C 4 -0.23410
O 5 -0.51880
O 6 -0.71400
H 7 0.41570
H 8 0.03940
H 9 0.10700
H 10 0.04270
H 11 0.08540
H 12 0.47280

Electrostatic charges on atoms

Calculation of the lowest unoccupied molecular orbital (LUMO) and the highest occupied molecular orbital (HOMO).

The LUMO indicates the properties of the molecule as a Lewis acid (electron acceptor) and the HOMO indicates the properties as a Lewis base (electron donor).
The calculation predict that the C3-O5 bond, a ketone can accept an electron from an electron donor like an alkohol.
The oxygen will readily donate an electron to a hydrogen, this reaction will result in a hemiketal.
Atom Number Mulliken ( Atomic Units ) Mulliken (LUMO) ( Atomic Units ) Mulliken (HOMO) ( Atomic Units )
O 1 -0.54036 0.02513 0.09467
C 2 0.23724 0.14970 0.04395
C 3 0.30324 0.30833 -0.01802
C 4 -0.43378 0.01558 0.01520
O 5 -0.41202 0.26483 0.45538
O 6 -0.55640 -0.09431 0.04305
H 7 0.37024 0.01080 -0.00816
H 8 0.12955 0.05484 0.08954
H 9 0.19323 0.06419 0.08660
H 10 0.16369 0.06603 0.09034
H 11 0.17661 0.05302 0.05875
H 12 0.36875 0.08188 0.04873

Reactivity as a Lewis acid

Reactivity as a Lewis base