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You are watching: Which of the following bonds can form between atoms of equal electronegativity

Lodish H, Berk A, Zipursky SL, et al. Molecular cell Biology. 4th edition. Brand-new York: W. H. Freeman; 2000.


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Carbohydrates show the prestige of subtle differences in covalent bonds in generatingmolecules with different biological activities. However, several varieties of noncovalent binding are an essential in keeping thethree-dimensional frameworks of big molecules such together proteins and also nucleic mountain (see number 2-1b). Noncovalent bond also allow one huge moleculeto bind specifically but transiently come another, making lock the basis of countless dynamicbiological processes.

The power released in the development of noncovalent binding is only1 – 5 kcal/mol, much much less than the shortcut energies that singlecovalent bond (see Table 2-1). Because the averagekinetic power of molecule at room temperature (25 °C) is around 0.6 kcal/mol, manymolecules will have actually enough power to break noncovalent bonds. Indeed, these weak bond sometimesare described as interactions fairly than bonds. Although noncovalent bondsare weak and have a transient presence at physiological temperatures(25 –  37 °C), multiple noncovalent bonds frequently acttogether to produce highly steady and particular associations in between different parts of a largemolecule or in between different macromolecules (Figure2-11). In this section we take into consideration the 4 main types of noncovalent bonds and also discusstheir duty in stability the structure of biomembranes.


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Figure 2-11

Multiple weak binding stabilize specific associations between big molecules. (Left) In this theoretical complex, seven noncovalent bonds bind the twoprotein molecule A and also B together, developing a stable complex. (Right)Because only four noncovalent (more...)


The Hydrogen link Underlies Water’s Chemical and Biological Properties

Hydrogen bonding between water molecules is of an essential importance because all life requiresan aqueous environment and water constitutes around 70–80 percent that the load ofmost cells. The common attraction the its molecules causes water to have actually melting and boilingpoints at least 100 °C greater than they would be if water were nonpolar; in the absenceof this intermolecular attractions, water on planet would exist generally as a gas. The exactstructure of fluid water is still unknown. That is believed to contain numerous transient, maximallyhydrogen-bonded networks. Many likely, water molecules space in rapid motion, constantly makingand breaking hydrogen bonds with nearby molecules. As the temperature that water increasestoward 100 °C, the kinetic power of its molecule becomes greater than the energy ofthe hydrogen bond connecting them, and the gaseous form of water appears.


Properties that Hydrogen Bonds

Normally, a hydrogen atom creates a covalent link with just one other atom. However, ahydrogen atom covalently external inspection to a donor atom, D, may type an additional weak association,the hydrogen bond, with an acceptor atom,A:

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In order because that a hydrogen bond come form, the donor atom need to beelectronegative, so that the covalent D—H bond is polar. The acceptor atom likewise mustbe electronegative, and its external shell must have actually at the very least one nonbonding pair of electronsthat attracts the δ+ charge of the hydrogen atom. In biologicalsystems, both donors and also acceptors are usually nitrogen or oxygen atoms, particularly thoseatoms in amino (—NH2) and also hydroxyl (—OH) groups. Since allcovalent N—H and also O—H bonds room polar, their H atoms deserve to participate inhydrogen bonds. Through contrast, C—H bonds room nonpolar, so this H atoms space almostnever connected in a hydrogen bond.

Water molecules administer a standard example that hydrogen bonding. The hydrogen atom in onewater molecule is attracted to a pair of electrons in the external shell of an oxygen atom in anadjacent molecule. Not just do water molecules hydrogen-bond with one another, they additionally formhydrogen binding with various other kinds that molecules, as shown in number 2-12. The visibility of hydroxyl (—OH) or amino(—NH2) groups makes many molecules dissolve in water. Because that instance, thehydroxyl team in methanol (CH3OH) and the amino group in methylamine(CH3NH2) can form several hydrogen bonds through water, enabling themolecules to dissolve in water come high concentrations. In general, molecules v polar bondsthat easily type hydrogen bonds v water deserve to dissolve in water and also are said to it is in hydrophilic (Greek,“water-loving”). As well as the hydroxyl and also amino groups, peptide and esterbonds are important chemical groups that connect well through water:

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Figure 2-12

Water readily develops hydrogen bonds. In liquid water, each water molecule apparently forms transient hydrogen bonds withseveral others, creating a liquid network the hydrogen-bonded molecule (a). The precisestructure of liquid water is still not known (more...)


Most hydrogen bonds room 0.26 – 0.31 nm long, about twice thelength of covalent bonds between the exact same atoms. In particular, the distance between thenuclei of the hydrogen and also oxygen atom of surrounding hydrogen-bonded molecules in water isapproximately 0.27 nm, around twice the length of the covalent O—H bond in water.The hydrogen atom is closer to the donor atom, D, to which it continues to be covalently bonded, thanit is come the acceptor. The length of the covalent D—H bond is a little longer 보다 itwould it is in if there were no hydrogen bond, due to the fact that the agree “pulls” thehydrogen away from the donor. The strength of a hydrogen shortcut in water (≈5 kcal/mol) ismuch weaker 보다 a covalent O—H shortcut (≈110 kcal/mol).


Hydrogen Bonds together a Stabilizing force in Macromolecules

An vital feature of all hydrogen bonds is directionality. In the the strongest hydrogenbonds, the donor atom, the hydrogen atom, and the acceptor atom all lie in a directly line.Nonlinear hydrogen bonds space weaker than straight ones; still, lot of nonlinear hydrogen bondshelp to stabilize the three-dimensional structures of many proteins. It is only due to the fact that of theaggregate strength of lot of hydrogen bonds the they beat a main role in thearchitecture of big biological molecule in aqueous services (see number 2-11).

The strengths of the hydrogen bonds in proteins and nucleic acids are just 1 come 2 kcal/mol,considerably weaker than the hydrogen bonds in between water molecules. The factor for thisdifference can be viewed from figure 2-13, which depictsthe development of a hydrogen bond between two amino mountain in a protein. Initially, both the—OH and also —NH2 teams in the protein space hydrogen-bonded towater, and the development of a hydrogen bond between these groups requires disruption of theirhydrogen bonds with water. For this reason the net change in energy in creating this—OH···N hydrogen bond will certainly be less than the 5kcal/mol properties of hydrogen bonds in between water molecules.


Figure 2-13

In order for a hydrogen link (red dots) to form between a —OH and an—NH2 group in a protein (right), the hydrogen bondsbetween this groups and water have to be disrupted (left).


Ionic Interactions are Attractions in between Oppositely fee Ions

In part compounds, the bonded atoms room so various in electronegativity that the bondingelectrons are never shared: this electrons are always found around the an ext electronegativeatom. In salt chloride (NaCl), for example, the bonding electron contributed by the sodiumatom is completely transferred come the chlorine atom. Also in solid crystals of NaCl, the sodiumand chlorine atoms are ionized, so the is much more accurate to compose the formula because that the compound asNa+Cl−.

Because the electrons are not shared, the bond in together compounds can not be consideredcovalent. Lock are, rather, ionic binding (orinteractions) that result from the attraction the a positively chargedion — a cation — for anegatively fee ion — an anion. Unlike covalent or hydrogenbonds, ionic bonds do not have fixed or details geometric orientations since theelectrostatic field around an ion — its attraction for anopposite charge — is uniform in all directions. However,crystals of salts such as Na+Cl− do have very regularstructures because that is the energetically most favorable means of packing together positiveand an unfavorable ions. The pressure that stabilizes ionic crystals is called the latticeenergy.

In aqueous solutions, straightforward ions of biological significance, together asNa+, K+, Ca2+,Mg2+, and also Cl−, do not exist as free, isolatedentities. Instead, every is surrounded by a stable, tightly held shell of water molecules (Figure 2-14). One ionic communication occurs in between the ion andthe oppositely charged finish of the water dipole, as shown below for the K+ion:
Figure 2-14

In aqueous solutions, a shell of water molecules surrounds ions. In the instance of a magnesium ion (Mg2+), six water molecules are heldtightly in location by electrostatic interactions between the two confident charges on the ionand the partial negative charge (more...)


Ions play crucial biological function when lock pass v narrow, protein-lined pores, orchannels, in membranes. Because that example, ionic activities through membranes are essential for theconduction that nerve impulses and for the stimulation the muscle contraction. Together we will view inChapter 21, ion must lose their shell of watermolecules in order come pass with ion channel proteins; channel proteins can then selectivelyadmit just Na+, or K+, or Ca2+ions, a selectivity vital for nerve function.

Most ionic compound are quite soluble in water since a large amount of power is releasedwhen ions tightly tie water molecules. This is recognized as the energy ofhydration. Oppositely fee ions are shielded native one an additional by the water andtend not to recombine. Salts prefer Na+Cl− dissolve inwater due to the fact that the power of hydration is better than the lattice energy that stabilizes thecrystal structure. In contrast, certain salts, together asCa3(PO4)2, are virtually insoluble in water; the largecharges top top the Ca2+ and also PO43− ions generatea formidable lattice energy that is better than the power of hydration.


Van der Waals interactions Are brought about by Transient Dipoles

When any kind of two atoms technique each other closely, they produce a weak, nonspecific attractiveforce that produces a van der Waals interaction,named for Dutch physicist johannes Diderik valve der Waals(1837 – 1923), who first described it. This nonspecificinteractions result from the momentary random fluctuations in the distribution of the electronsof any kind of atom, which provide rise to a transient unequal circulation of electrons, that is, atransient electric dipole. If 2 noncovalently bonded atoms are close enough together, thetransient dipole in one atom will certainly perturb the electron cloud of the other. This perturbationgenerates a transient dipole in the second atom, and also the two dipoles will tempt each otherweakly. Similarly, a polar covalent bond in one molecule will tempt an oppositely orienteddipole in another.

Van der Waals interactions, involving either transient induced or permanent electric dipoles,occur in all types of molecules, both polar and also nonpolar. In particular, valve der Waalsinteractions space responsible because that the cohesion between molecules the nonpolar liquids and also solids,such as heptane,CH3—(CH2)5—CH3, that cannotform hydrogen bond or ionic interaction with various other molecules. As soon as these strongerinteractions room present, they override most of the influence of valve der Waals interactions.Heptane, however, would certainly be a gas if valve der Waals interactions could not form.

The toughness of valve der Waals interactions decreases promptly with increasing distance; thusthese noncovalent bond can form only as soon as atoms are quite close to one another. However, ifatoms obtain too nearby together, they become repelled by the negative charges in their outerelectron shells. Once the van der Waals attraction between two atoms precisely balances therepulsion in between their two electron clouds, the atom are said to be in valve der Waalscontact (Figure 2-15). Each type of atom has avan der Waals radius in ~ which the is in valve der Waals call with other atoms. The valve derWaals radius of an H atom is 0.1 nm, and also the radii the O, N, C, and S atoms are between 0.14 and0.18 nm. 2 covalently external inspection atoms space closer with each other than two atoms the are merely in vander Waals contact. Because that a valve der Waals interaction, the internuclear street is approximatelythe sum of the equivalent radii because that the two participating atoms. Therefore the distance in between aC atom and also an H atom in van der Waals contact is 0.27 nm, and also between 2 C atom is 0.34 nm.In general, the van der Waals radius of an atom is about twice as lengthy as its covalent radius.For example, a C—H covalent link is about 0.107 nm long and also a C—C covalentbond is about 0.154 nm long.


Figure 2-15

Two oxygen molecule in valve der Waals contact. Transient dipoles in the electron clouds of every atoms provide rise come weak attractive forces,called van der Waals interactions. Each type of atom has a characteristic van der Waalsradius in ~ which van der Waals (more...)


The power of the valve der Waals interaction is around 1 kcal/mol, just slightly higher thanthe median thermal energy of molecule at 25 °C. Thus the van der Waals interaction iseven weaker 보다 the hydrogen bond, which frequently has an energy of1 – 2 kcal/mol in aqueous solutions. The attraction between twolarge molecules deserve to be appreciable, however, if they have exactly complementary shapes, sothat they make countless van der Waals contacts when they come right into proximity. Van der Waalsinteractions, as well as other noncovalent bonds, adjust the binding of countless enzymes withtheir details substrates (the building materials on whichan enzyme acts) and also of each form of antibody through its certain antigen (Chapter 3).


Hydrophobic Bonds reason Nonpolar molecule to Adhere come One Another

Nonpolar molecules carry out not contain ions, possess a dipole moment, or become hydrated. Becausesuch molecules room insoluble or virtually insoluble in water, lock are stated to it is in hydrophobic (Greek,“water-fearing”). The covalent bonds in between two carbon atoms and also betweencarbon and also hydrogen atoms are the most typical nonpolar bonds in biological systems.Hydrocarbons — molecules comprised only of carbon andhydrogen — are virtually insoluble in water. A largetriacylglycerol (or triglyceride) such together tristearin, a ingredient of pet fat, is alsoinsoluble in water, also though its six oxygen atoms get involved in part slightly polar bondswith surrounding carbon atom (Figure 2-16). As soon as shaken inwater, tristearin creates a separate phase comparable to the separation that oil from the water-basedvinegar in one oil-and-vinegar salad dressing.


Figure 2-16

The chemical structure of tristearin, or tristearoyl glycerol, a component of naturalfats. It includes three molecules of the fatty acid stearic acid,CH3(CH2)16COOH, esterified to one molecule the glycerol,HOCH2CH(OH)CH2OH. One finish of the molecule (green) (more...)


The pressure that reasons hydrophobic molecules or nonpolar parts of molecules to aggregatetogether quite than come dissolve in water is dubbed the hydrophobic bond. This is no a separate bonding force; rather, it is the an outcome ofthe power required to insert a nonpolar molecule into water. A nonpolar molecule can not formhydrogen bonds through water molecules, so that distorts the usual water structure, forcing thewater into a rigid cage the hydrogen-bonded molecules around it. Water molecules are typically inconstant motion, and the formation of together cages restricts the activity of a variety of watermolecules; the effect is to increase the structural organization of water. This situation isenergetically unfavorable due to the fact that it reduce the randomness (entropy) that the population ofwater molecules. The duty of entropy in chemical equipment is discussed further in a latersection.

The opposition of water molecules to having actually their motion limited by developing cages aroundhydrophobic molecules or sections thereof is the major reason molecule such as tristearin andheptane are basically insoluble in water and also interact greatly with other hydrophobicmolecules. Nonpolar molecule can also bond together, albeit weakly, with van der Waalsinteractions. The net result of the hydrophobic and also van der Waals interactions is a verypowerful propensity for hydrophobic molecule to connect with one another, and also not withwater.

Small hydrocarbons choose butane(CH3—CH2—CH2—CH3)are rather soluble in water, since they can dissolve without disrupting the water latticeappreciably. However, 1-butanol(CH3—CH2—CH2—CH2OH)mixes fully with water in every proportions. The instead of of simply one hydrogen atom withthe polar —OH group allows the molecule to type hydrogen bonds with water and greatlyincreases its solubility.

Simply put, prefer dissolves like. Polar molecule dissolve in polar solventssuch together water, while nonpolar molecule dissolve in nonpolar solvents such as hexane.


Multiple Noncovalent Bonds have the right to Confer Binding Specificity

Besides contributing come the stability of huge biological molecules, multiple noncovalentbonds can likewise confer specificity by determining how huge molecules will foldor which areas of various molecules will certainly bind together. All types of these weakinteractions are reliable only over a short variety and need close contact in between thereacting groups. Because that noncovalent bond to type properly, there should be a complementaritybetween the website on the two interacting surfaces. Figure2-17 illustrates exactly how several various weak bonds have the right to bind two protein chains together.Almost any kind of other plan of the same teams on the 2 surfaces would not enable themolecules to tie so tightly. Such multiple, details interactions permit protein molecule tofold right into a unique three-dimensional form (Chapter3) and also the 2 chains that DNA to bind together (Chapter 4).


Figure 2-17

The binding of a hypothetical pair of proteins by 2 ionic bonds, one hydrogen bond,and one large combination of hydrophobic and van der Waals interactions. The structural complementarity the the surfaces of the 2 molecules gives rise to thisparticular (more...)


Phospholipids space Amphipathic Molecules

Multiple noncovalent bonds additionally are an important in stabilizing the structure of biomembranes, who primary materials are phospholipids. Since the vital properties ofbiomembranes derive from phospholipids, we first examine the chemistry of this compounds andthen see just how they associate right into the sheetlike frameworks that space the foundation ofbiomembranes.

All phospholipids contain one or more acyl chains derived from fat acids, which consist that a hydrocarbon chain attached come a carboxylgroup (—COOH). Fatty acids are insoluble in water and salt solutions; they different inlength and also in the extent and position that their dual bonds. Table 2-2 perform the major fatty acids discovered in cells. Most fatty acids have actually aneven number of carbon atoms, generally 16, 18, or 20.


Fatty acids with no dual bonds are said to be saturated; those v atleast one dual bond space unsaturated. Unsaturated fatty acid chains normallyhave one double bond, yet some have actually two, three, or four. Two stereoisomeric configurations, cisand trans, are feasible around each twin bond:


A cis double bond introduces a strictly kink in the otherwise flexible straight chain that a fatty mountain (Figure 2-18). In general, the fat acids inbiological equipment contain only cis twin bonds.


Figure 2-18

The effect of a double bond. Presented are space-filling models and chemical structures of the ionized type of palmiticacid, a saturated fatty acid, and oleic acid, one unsaturated one. In saturated fat acids,the hydrocarbon chain is linear; the cis double (more...)


Phospholipids consist of 2 long-chain fatty acyl groups linked (usually by an ester bond)to small, extremely hydrophilic groups. Consequently, unlike tristearin, phospholipids execute notclump with each other in droplets but orient us in sheets, exposing your hydrophilic ends tothe aqueous environment. Molecules in i beg your pardon one end (the “head”) interactswith water and also the other finish (the “tail”) is hydrophobic are claimed to beamphipathic (Greek, “tolerant ofboth”). The tendency of amphipathic molecule to form organized structuresspontaneously in water is the an essential to the framework of cabinet membranes.

In phosphoglycerides, a principal course of phospholipids, fatty acyl next chains areesterified to 2 of the 3 hydroxyl groups in glycerol


but the 3rd hydroxyl group is esterified to phosphate. The easiest phospholipid,phosphatidic acid, includes only this components:
whereR1 and R2 are fatty acyl groups.

In many phospholipids, however, the phosphate group is likewise esterified to a hydroxyl group onanother hydrophilic compound. In phosphatidylcholine, for example, choline is attached come thephosphate (Figure 2-19). In various other phosphoglycerides, thephosphate group is linked to other molecules, such together ethanolamine, the amino acid serine, orthe sugar inositol. The negative charge top top the phosphate and also the charged teams orhydroxyl teams on the alcohol esterified to it interact strongly v water.


Figure 2-19

Phosphatidylcholine, a usual phosphoglyceride, has actually a hydrophobic tail and ahydrophilic head in i m sorry choline is connected to glycerol through phosphate. One of two people or both that the fatty acyl next chains in a phosphoglyceride may be saturation orunsaturated.


The Phospholipid Bilayer creates the an easy Structure of all Biomembranes

When a suspension of phospholipids is mechanically spread in aqueous solution, castle canassume three various forms: micelles, double layer sheets, and also liposomes (Figure 2-20). The form of structure created by a pure phospholipid or amixture that phospholipids depends on the size of the fatty acyl chains and their level ofsaturation, ~ above the temperature, on the ionic ingredient of the aqueous medium, and also on the modeof dispersal of the phospholipids in the solution. In all 3 forms, hydrophobic interactionscause the fatty acyl chain to aggregate and exclude water molecule from the“core.” Micelles space rarely created from organic phosphoglycerides, whosefatty acyl chains usually are too bulky to fit into the internal of a micelle.


Figure 2-20

Cross-sectional see of the three frameworks that deserve to be formed by mechanicallydispersing a suspension that phospholipids in aqueous solutions. Shown are a spherical micelle through a hydrophobic inner composed completely of fatty acylchains; a spherically (more...)


Under suitable conditions, phospholipids that the composition current in cells spontaneouslyform symmetric sheetlike structures, referred to as phospholipidbilayers, that room two molecule thick. Every phospholipid class in this lamellarstructure is dubbed a leaflet. The hydrocarbon side chains in every leafletminimize call with water through aligning us tightly together in the facility of thebilayer, forming a hydrophobic core that is around 3 nm thick. The close packing of thesehydrocarbon side chains is stabilized by valve der Waals interactions in between them. Ionic andhydrogen binding stabilize the interaction of the phospholipid polar head teams with every otherand through water. At neutral pH, the polar head teams in part phospholipids (e.g.,phosphatidylcholine) have actually no net electrical charge, whereas the head groups in others have a netnegative charge. Nonetheless, all phospholipids can pack together into the characteristicbilayer structure.

A phospholipid bilayer can be of almost unlimited size — frommicrometers (µ) to millimeters (mm) in size orwidth — and deserve to contain 10s of countless phospholipidmolecules. Due to the fact that of your hydrophobic core, bilayers are impermeable come salts, sugars, andmost other little hydrophilic molecules. Like a phospholipid bilayer, all organic membraneshave a hydrophobic core, and they all different two aqueous solutions. The plasma membrane, for example, the end the interior ofthe cell from that is surroundings. Similarly, the membranes that surround the oribelles ofeukaryotic cells separate one aqueous phase — the cellcytosol — from another — theinterior the the organelle. Several species of evidence indicate the the phospholipid double layer isthe an easy structural unit of almost all biomembranes (Chapter 5). Linked with membrane phospholipids are miscellaneous proteins the helpconfer unique properties top top each type of membrane. We define the general structure ofmembrane proteins and their association through the phospholipid bilayer in chapter 3.


 Noncovalent bonds recognize the shape of plenty of largebiological molecules and also stabilize complexes written of 2 or more different molecules.
 Ionic bonds an outcome from the electrostatic attraction betweenthe positive and an unfavorable charges of ions. In aqueous solutions, all cations and also anions aresurrounded through a strict bound shell of water molecules.

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