We examined the ionization potential (IP) corresponding to the free energy of a hole oil duplex DNA by semiempirical molecular orbital theory with a continuum solvent model. As for the contiguous guanines (a guanine run), we found that the IP ill the gas phase significantly decreases with the increasing number of nucleotide pairs of the guanine Rill, Whereas the IP in water (OP, oxidation potential) only slightly does. The latter result is consistent with the experimental result for DNA oligomers in water. This decrease in the IP is mainly due to the attractive electrostatic interaction between the hole and a nucleotide pair in the duplex DNA. This interaction is reduced in water, which results in the small decrease in the IP in water. This mechanism explains the discrepancy between the experimental result and the previous computational results obtained by neglecting the solvent. As for the chemically modified guanine, the previous work showed that the removal of some solvent (water) molecules due to the attachment of a neutral functional group to a guanine in a duplex DNA stabilizes the hole oil the guanine. One might naively have expected the opposite case, since a polar Solvent usually stabilizes ions. This mechanism also explains this unexpected stabilization of a hole as follows. When some water molecules ire removed, the attractive electrostatic interaction stabilizing the hole increases, and thus, the hole is stabilized. Ill order to design the hole energetics by a chemical modification of DNA, this mechanism has to be taken into account and can be used.