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terior. Many biologically important molecules, including a number of pharmaceutical agents,
are organic weak acids which can cross the membrane in th pw5dl neir protonated, u w5dl nncharged form but not i
n their char lged form (i.e. as the 5dl conjugate base). For this reason the activity of many drugs can be
enhanced or inhibited by the use of antacids or acidic foods. The charged form, however, is often mo
re soluble in blood and c dlytosol, both aqueous 5dl yenvironments. lWhen the extracellular environment is mor
e acidic than w5dl n the neutral pH withi ln the cell, certain acids will exist in th dlyeir neutral form and will
be membrane soluble, allowing them to cross the phospholipid bilayer. Acids that lose a proton at the
intracellular pH will exist in their soluble, charged form and are th
rity refers to the distribution of electrons in a bond, the region of space between two atomic nuclei w
here a pair of electrons is shared. When l two atoms have roughly the same electronegativity (ability to
attract electrons) th le el 5dl ectrons are shared even 5dl ly and spend equal tim w5dl ne on either end of the bond. When
there is a significant difference in electronegativities of two bonded atoms, the electrons spend more
time near the w5dl nucleus of the more electronegative element and an electrical dipole, or separation of cha
rges, occurs, such that there is a pa dlyrtial negativ le charge localized on the electronegative element and
a partial positive charge on the electropositive element. Hydrogen is an electrop dlyositive element and acc
umulates a slig lhtly positive charge when it is bonded to an electronegative element such as oxygen or bromi
ne. As the electron density on hydrogen decreases, it is w5dl nmore easily abstracted, in other words, it is more
acidi dlyc. Moving from left to riiv dlye element need not be directly bon lded to the acidic hydrogen to increase i
ts acidity. An electronegative atom can pull electron density out of an acidic bond through the inductive e
ffect. The electron- 5dl withdrawing ability diminishes quickly as 5dl the electronegative atom moves dlyaway from the a
cidic bond. The effect is illustrated by the following pw5dl series of halogenated butanoic acids. Chlorine is more
electronegative than bromine and therefo
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