Essential Cell Biology 5th edition
68PANEL 2–2 THE CHEMICAL PROPERTIES OF WATERHYDROGEN BONDSBecause they are polarized, twoadjacent H 2 O molecules can forma noncovalent linkage known as ahydrogen bond. Hydrogen bondshave only about 1/20 the strengthof a covalent bond.Hydrogen bonds are strongest whenthe three atoms lie in a straight line.δ +δ +HHδ _ δ +OH O δ _H hydrogenδ + bondHHbond lengthsOhydrogenbond0.17 nmHO0.10 nmcovalent bondWATERTwo atoms connected by a covalent bond may exert different attractions forthe electrons of the bond. In such cases, the bond is polar, with one endslightly negatively charged (δ _ ) and the other slightly positively charged (δ + ).WATER STRUCTUREMolecules of water join together transientlyin a hydrogen-bonded lattice.H δ+electropositiveregionOδ +Hδ _ δ _electronegativeregionAlthough a water molecule has an overall neutral charge (having the samenumber of electrons and protons), the electrons are asymmetrically distributed,making the molecule polar. The oxygen nucleus draws electrons away fromthe hydrogen nuclei, leaving the hydrogen nuclei with a small net positive charge.The excess of electron density on the oxygen atom creates weakly negativeregions at the other two corners of an imaginary tetrahedron. On these pages,we review the chemical properties of water and see how water influences thebehavior of biological molecules.The cohesive nature of water isresponsible for many of its unusualproperties, such as high surface tension,high specific heat capacity, and high heatof vaporization.HYDROPHILIC MOLECULESSubstances that dissolve readily in water are termed hydrophilic. They includeions and polar molecules that attract water molecules through electrical chargeeffects. Water molecules surround each ion or polar molecule and carry itinto solution.HH HOH OOδ _ Oδ _ HHδ + HHδ +δ _ Na + H Hδ + Cl _Oδ _ δ _ O O H Hδ + δ +HH OH O HHO HHIonic substances such as sodium chloridedissolve because water molecules areattracted to the positive (Na + ) or negative(Cl _ ) charge of each ion.HOOHHHHHOHOCOHHHNNHHHOHOHHHPolar substances such as ureadissolve because their moleculesform hydrogen bonds with thesurrounding water molecules.HYDROPHOBIC MOLECULESSubstances that contain a preponderanceof nonpolar bonds are usually insolublein water and are termed hydrophobic.Water molecules are not attracted to suchhydrophobic molecules and so have littletendency to surround them and bring theminto solution.HH OH HH HHOHCHCCHHHHydrocarbons, which contain manyC–H bonds, are especially hydrophobic.OHOOHHHHOOHHH
69WATER AS A SOLVENTMany substances, such as household sugar (sucrose), dissolve in water. That is, theirmolecules separate from each other, each becoming surrounded by water molecules.watermoleculesugar crystalsugardissolvessugar moleculeWhen a substance dissolves in aliquid, the mixture is termed a solution.The dissolved substance (in this casesugar) is the solute, and the liquid thatdoes the dissolving (in this case water)is the solvent. Water is an excellentsolvent for hydrophilic substancesbecause of its polar bonds.ACIDSSubstances that release hydrogen ions (protons) into solutionare called acids.HYDROGEN ION EXCHANGEPositively charged hydrogen ions (H + ) can spontaneouslymove from one water molecule to another, thereby creatingtwo ionic species.HClhydrochloric acid(strong acid)Many of the acids important in the cell are not completelydissociated, and they are therefore weak acids—for example,the carboxyl group (–COOH), which dissociates to give ahydrogen ion in solution.COOHcarboxyl group(weak acid)H +hydrogen ionNote that this is a reversible reaction.H + ++Cl –chloride ionCH HO H OHoften written as:OO –Because the process is rapidly reversible, hydrogen ions arecontinually shuttling between water molecules. Pure watercontains equal concentrations of hydronium ions andhydroxyl ions (both 10 –7 M).H+OHhydronium ionhydroxyl ionH 2 O H + + OH –hydrogenionH +OHhydroxylionpHThe acidity of asolution is definedby the concentration (conc.)of hydronium ions (H 3 O + ) itpossesses, generallyabbreviated as H + .For convenience, weuse the pH scale, wherepH = _ log 10 [H + ]For pure water[H + ] = 10 _ 7 moles/literpH = 7.0H +conc.moles/literACIDICBASIC1 010 _ 110 _ 210 _ 310 _ 410 _ 510 _ 610 _ 710 _ 810 _ 910 _ 1010 _ 1110 _ 1210 _ 1310 _ 14pH1234567891011121314BASESSubstances that reduce the number of hydrogen ions insolution are called bases. Some bases, such as ammonia,combine directly with hydrogen ions.NH 3ammonia+ H +hydrogen ionNH 4+ammonium ionOther bases, such as sodium hydroxide, reduce the number ofH + ions indirectly, by producing OH – ions that then combinedirectly with H + ions to make H 2 O.NaOH Na + +sodium hydroxidesodium(strong base)ionOH –hydroxylionMany bases found in cells are partially associated with H + ionsand are termed weak bases. This is true of compounds thatcontain an amino group (–NH 2 ), which has a weak tendencyto reversibly accept an H + ion from water, therebyincreasing the concentration of free OH – ions.–NH 2 + H + + –NH 3Panel 2.02b
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69
WATER AS A SOLVENT
Many substances, such as household sugar (sucrose), dissolve in water. That is, their
molecules separate from each other, each becoming surrounded by water molecules.
water
molecule
sugar crystal
sugar
dissolves
sugar molecule
When a substance dissolves in a
liquid, the mixture is termed a solution.
The dissolved substance (in this case
sugar) is the solute, and the liquid that
does the dissolving (in this case water)
is the solvent. Water is an excellent
solvent for hydrophilic substances
because of its polar bonds.
ACIDS
Substances that release hydrogen ions (protons) into solution
are called acids.
HYDROGEN ION EXCHANGE
Positively charged hydrogen ions (H + ) can spontaneously
move from one water molecule to another, thereby creating
two ionic species.
HCl
hydrochloric acid
(strong acid)
Many of the acids important in the cell are not completely
dissociated, and they are therefore weak acids—for example,
the carboxyl group (–COOH), which dissociates to give a
hydrogen ion in solution.
C
O
OH
carboxyl group
(weak acid)
H +
hydrogen ion
Note that this is a reversible reaction.
H + +
+
Cl –
chloride ion
C
H H
O H O
H
often written as:
O
O –
Because the process is rapidly reversible, hydrogen ions are
continually shuttling between water molecules. Pure water
contains equal concentrations of hydronium ions and
hydroxyl ions (both 10 –7 M).
H
+
O
H
hydronium ion
hydroxyl ion
H 2 O H + + OH –
hydrogen
ion
H +
O
H
hydroxyl
ion
pH
The acidity of a
solution is defined
by the concentration (conc.)
of hydronium ions (H 3 O + ) it
possesses, generally
abbreviated as H + .
For convenience, we
use the pH scale, where
pH = _ log 10 [H + ]
For pure water
[H + ] = 10 _ 7 moles/liter
pH = 7.0
H +
conc.
moles/liter
ACIDIC
BASIC
1 0
10 _ 1
10 _ 2
10 _ 3
10 _ 4
10 _ 5
10 _ 6
10 _ 7
10 _ 8
10 _ 9
10 _ 10
10 _ 11
10 _ 12
10 _ 13
10 _ 14
pH
1
2
3
4
5
6
7
8
9
10
11
12
13
14
BASES
Substances that reduce the number of hydrogen ions in
solution are called bases. Some bases, such as ammonia,
combine directly with hydrogen ions.
NH 3
ammonia
+ H +
hydrogen ion
NH 4
+
ammonium ion
Other bases, such as sodium hydroxide, reduce the number of
H + ions indirectly, by producing OH – ions that then combine
directly with H + ions to make H 2 O.
NaOH Na + +
sodium hydroxide
sodium
(strong base)
ion
OH –
hydroxyl
ion
Many bases found in cells are partially associated with H + ions
and are termed weak bases. This is true of compounds that
contain an amino group (–NH 2 ), which has a weak tendency
to reversibly accept an H + ion from water, thereby
increasing the concentration of free OH – ions.
–NH 2 + H + + –NH 3
Panel 2.02b