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The reason its LogD does not decrease appreciably after it is deprotonated is, again, because the negative charge is delocalized within the molecule in internal hydrogen bonding, such that it becomes a lipophilic anion and so can act as the all-important intramembrane proton shunt (28)

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doi: 10.1016/j.abb.2003.12.029 114 NakashimaMSuzukiKMeirmanovSNarukeYMatsuu-MatsuyamaMShichijoKet al