d-glyceraldehyde results summary

The electrostatic charges on the atoms of d-glyceraldehyde. A negative charge is red, a positive charge is blue and white atoms have no electric charge.
Atom Number Mulliken CHelpG
O 1 -0.39962 -0.45210
C 2 0.19417 0.38840
C 3 0.04563 0.26970
H 4 0.16712 0.04490
O 5 -0.50852 -0.62390
C 6 -0.09107 0.26630
O 7 -0.51551 -0.65920
H 8 0.12764 0.00160
H 9 0.36035 0.38200
H 10 0.12263 -0.04360
H 11 0.14896 -0.00080
H 12 0.34823 0.42680

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 C2-O1 bond, a aldehyde 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 hemiacetal.
Atom Number Mulliken Mulliken (LUMO) Mulliken (HOMO)
O 1 -0.39962 0.20863 0.47385
C 2 0.19417 0.64473 0.01370
C 3 0.04563 -0.51547 -0.07030
H 4 0.16712 0.06538 0.09947
O 5 -0.50852 0.06165 0.10722
C 6 -0.09107 0.39903 0.06673
O 7 -0.51551 0.02240 0.02606
H 8 0.12764 0.06818 0.19075
H 9 0.36035 0.00317 -0.01348
H 10 0.12263 -0.00546 0.02597
H 11 0.14896 0.01470 0.04223
H 12 0.34823 0.03307 0.03781

Reactivity as a Lewis acid

Reactivity as a Lewis base