d-glucose results summary

The electrostatic charges on the atoms of d-glucose . A negative charge is red, a positive charge is blueand white atoms have no electric charge.
Atom Number Mulliken CHelpG
O 1 -0.37786 -0.46130
C 2 0.07649 0.46210
C 3 0.15997 0.24000
H 4 0.15561 0.01180
O 5 -0.58985 -0.58280
C 6 0.06166 0.06840
H 7 0.16098 0.12590
O 8 -0.56285 -0.61750
C 9 0.11125 0.11940
H 10 0.13000 0.09230
O 11 -0.47497 -0.59490
C 12 -0.09457 0.23550
H 13 0.14937 0.09460
O 14 -0.55731 -0.75750
C 15 -0.06661 0.20290
O 16 -0.58312 -0.73390
H 17 0.13760 -0.02350
H 18 0.38179 0.37420
H 19 0.39040 0.39540
H 20 0.35511 0.38450
H 21 0.38359 0.47860
H 22 0.15613 0.01010
H 23 0.13260 0.02810
H 24 0.36462 0.44760

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 C2-01 bond, an aldehyde can accept an electron from an electron donor like an alkohol.
The C9-O11 bond is the Lewis base (electron donor). Any hydroxyl group can act as a Lewis base. In this case we calculated the HOMO for d-glucose in vacuum at the equilibrium structure calculated during geometry optimization. Depending on the environment ( e.g. d-glucose in aquous solution vs d-glucose in vacuum) and the configuration used for the calculation the HOMO will designate another hydroxyl group as the Lewis base.
Atom Number Mulliken Mulliken (LUMO) Mulliken (HOMO)
O 1 -0.37786 0.25144 0.04600
C 2 0.07649 0.26234 0.00631
C 3 0.15997 -0.08053 -0.01228
H 4 0.15561 0.11212 0.02728
O 5 -0.58985 0.05101 -0.00299
C 6 0.06166 -0.02210 -0.01934
H 7 0.16098 0.02910 0.07622
O 8 -0.56285 0.03188 0.03832
C 9 0.11125 0.00357 -0.12429
H 10 0.13000 0.01913 0.11482
O 11 -0.47497 0.02028 0.41290
C 12 -0.09457 -0.00746 0.00975
H 13 0.14937 0.01943 0.06761
O 14 -0.55731 -0.01171 0.03752
C 15 -0.06661 0.00533 0.00501
O 16 -0.58312 0.00444 0.02274
H 17 0.13760 0.18362 0.02980
H 18 0.38179 0.03563 0.03005
H 19 0.39040 0.01558 0.02209
H 20 0.35511 0.01382 0.08568
H 21 0.38359 0.01991 0.04313
H 22 0.15613 0.01562 0.00617
H 23 0.13260 0.01062 0.04414
H 24 0.36462 0.01692 0.03338

Reactivity as a Lewis acid

Reactivity as a Lewis base