Solutions and Non-Covalent Binding Forces

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1 Chapter 3 Solutions and Non-Covalent Binding Forces 3.1 Solvent and solution properties Molecules stick together using the following forces: dipole-dipole, dipole-induced dipole, hydrogen bond, van der Waals/London, dispersion forces, solvophobic forces, Lewis acid-base interactions, metal coordination, charge transfer interactions. Most common solvents interact with other solvent molecules or solutes using dipole-dipole, hydrogen bonding, and London dispersion forces Solvent scales - Protic solvent: has a hydrogen atom attached to a heteroatom, such as O, N, or S, and can form hydrogen bonds with a solute molecule as well as with other solvent molecules. - Aprotic solvent: lacks a hydrogen on a heteroatom, and therefore cannot act as a donor. - A polar solvent can be described as a solvent that can solubilize salts or molecules with large permanent dipoles, while a nonpolar solvent is one that does not. Dielectric constants (ε) - a constant to determine whether a solvent is polar or nonpolar, with higher ε values reflecting greater polarity. - is measured by determining the effect of an intervening solvent on the electric field between two oppositely charged plates. - Large molecular dipoles, large molecular polarizabilities, and hydrogen bonding sites on the solvent molecules combine to give large dielectric constants.

2 Large dipole, hydrogen bonding capability and more polarizable than water - ε = ε μ /ε o ; defined as the ratio of the permittivity of the medium (ε μ ) to the permittivity of a vacuum (ε o ). - This constant gives insights into how well the solvent screen electrostatic forces. - solvents with high dielectric constants more efficiently screen the attractive or repulsive forces between ions and the ends of dipoles.

3 3.1.3 Solubility

4 3.2 Binding forces Intermolecular and intramolecular interactions Ion pairing interactions Electrostatic interactions q 1 r ε q 2 Coulomb s law E: attractive or repulsive potential E between two charges q 1 and q 2 ε: dielectric constant of the medium r: distance Salt bridges: an ion pair between two side chains of a protein 0-2 kcal/mol Asp or Glu.. Lys or Arg up to 3 kcal/mol

5 3.2.2 Electrostatic interactions involving dipoles Ion-dipole interactions μ = q 1 l Solvation of ions Li + > Na + > K + > Rb + The smaller the ion, the greater the hydration energy. This trend is an indication of a largely electrostatic effect.

6 Dipole-dipole interactions

7 3.2.3 Hydrogen bonding Hydrogen bond is described as a Coulombic interaction between a polar donor (Dn δ- -HD δ+ ) And an acceptor atom (:Ac δ- ). Since the hydrogen bond is a simple Coulombic interaction, any partial negative charge can Accept a hydrogen bond, not just electronegative atoms, but even π systems. Unusual hydrogen bond acceptor

8 Geometry Since electrostatic considerations dominate for most hydrogen bonds, the geometry of the Hydrogen bond is not a major contributing factor to strength. Still, the optimal geometry has a collinear arrangement of the three atoms involved, even though significant deviations from linearity can be tolerated. Three-center hydrogen bonds or bifurcated ( 두갈래로갈라진 ) HB

9 Strengths of normal HBs Very strong HBs: kcal/mol Moderate HBs: 5-14 kcal/mol Weak HBs: 0-4 kcal/mol (most common HBs) - Consistent with the elctrostatic model, there is a general trend that the hydrogen bonds is stronger if one or both of the partners is charged, meaning that the electrostatic nature significantly increases due to large Coulombic attraction. 1. Solvation effects Solvent: the factor that most influences the strength of a HB because the donor and acceptor are solvated prior to formation of Dn-H--:Ac hydrogen bond. HB strength for Gas phase or nonpolar solvents: 5-10 kcal/mol HB strength in the interior of a protein that is dissolved in water: kcal/mol HB strength not in the interior of a protein: ~0 kcal/mol When one of the components, either the donor or acceptor, is charged, HB strength: kcal/mol.

10 2. Electronegativity effects For the donors HF > HCl > HBr > HI (depending on charge on hydrogen) CF 3 CO 2 H > CCl 3 CO 2 H > CBr 2 CO 2 H > CI 3 CO 2 H (the same atom -> depending on acidity) For the acceptors H 2 O > H 3 N > HS > H 3 P Electronegativity increases the δ- on the atom, which is good for hydrogen bonding, but it makes the element less willing to share its electrons, which is bad for hydrogen bonding. -> Bonds to F are quite polar, but F is a very poor hydrogen bond acceptor (i.e. Poor electron donor). Hydrogen bonds involving F as the acceptor are actually rare. The poor hydrogen bonding see with S and P is likely due to the very diffuse nature of the lone pairs in third row elements.

11 3. Resonance assisted HBsc

12 4. Polarization enhanced HBs (also known as cooperative HBs) Cyclic trimer: 5.6 kcal/mol Cyclic pentamer: 10.6 kcal/mol Cyclic hexamer: 10.8 kcal/mol

13 5. Secondary interactions in hydrogen bonding systems 6. Cooperativity in HBs The repeating structure of the a-helix reinforces itself. Once a few hydrogen bonds are Formed, the system naturally propagates and each hydrogen bond reinforces the next. This can be viewed as an entropic effect. The first few HBs pay most of the entropic cost, Making it more and more favorable to continue the stretch of hydrogen bonding.

14 Vibrational properties of HBs Normal HBs Low barrier HBs no barrier HBs significant energy barrier Short strong HBs

15 Short distance Steric compression pka

16 3.2.4 π effects Cation-π interactions Permanent quadrupole moment Quadrupole: is simply two dipoles aligned in such a way that there is no net dipole (if there was a dipole, we d have a dipole, not a quadrupole). Li + > Na + > K + > Rb +

17 CH 3 NH OCCH 3 (electrostatic interactions): ~120 kcal/mol in the gas phase, <2 kcal/mol in water CH 3 NH 3+.benzene (cation-π interactions): ~18 kcal/mol in the gas phase, ~5 kcal/mol in water In proteins, Lys / Arg interact with Phe / Tyr / Trp +H 3 N CO 2 - +H 3 N CO 2 - NH 3 + CO 2 - NH 3 + CO 2 - NH 3 + CO 2 - NH HN +H 3 N +H 2 N OH Lys Arg NH 2 Phe Tyr Trp e.g) Nicotine receptor Acetylcholine (Ach) Me Me N Me O O

18 Polar-π interactions Gas phase (binding energy) kcal/mol Water binds cations electrostatically by aligning its large permanent dipole moment. Benzene binds cations electrostatically by aligning its large permanent quadrupole moment. benzoic acid pk a = 4.2 pk a = 6.39 CO 2 - destabilized

19 Aromatic-aromatic interactions (π stacking) Adverse electrostatic interactions In some more complicated structures the T-shaped geometry cannot be obtained. In these cases, then, it is best to form a displaced or slipped stack. This still aligns regions of positive electrostatic potential with regions of negative electrostatic potential.

20 π Donor-acceptor interactions A donor-acceptor interaction occurs between any two molecules, or regions of a molecule, where one has a low energy empty orbital (acceptor) and the other a high energy filled orbital (donor). When these two orbitals are aligned properly, some extent of charge transfer can occur from the donor to the acceptor. This is stabilizing interaction. electron poor electron rich Generally, a large extent of charge transfer leads to colors. No new bonds are formed, however, as each partner can be re-isolated intact. The color arises from an absorbance of light that promotes an electron from the donor to the acceptor the full charge transfer occurs in the excited state, while only orbital mixing occurs in the ground state. Charge transfer complexes

21 3.2.6 The hydrophobic effect - This effect drives the association of organics together in water. - Hydrocarbons and related organic compounds are insoluble in water. - This effect is single most important component in biological molecular recognition. - It is the strongest contributor to protein folding, membrane formation, and in most cases, small molecule binding by receptors in water. Aggregation of organics The hydrophobicity of organic groups can be measured by the partitioning of organic molecules between a nonpolar solvent, typically n-octanol, and water. hydrophobicity constant = P o : the partitioning of an organic molecule between octanol and water without R P : the partitioning of an organic molecule between octanol and water with R attached

22 More compact gas phase, 70:30 (anti:gauche) liquid butane in water, 55:45 (anti:gauche) For large molecules that can experience more substantial changes in surface area as a result of conformational changes, the effect could be quite large. -> the primary driving force for protein folding phospholipids hydrophilic micelle: a rough spherical structure amphiphilic hydrophobic Critical micelle concentration: a concentration where micelle is formed Vesicles: bilayers

23 The origin of the hydrophobic effect hydrocarbon While ice has a low enthalpy than water due to more hydrogen bonds, it is entropically disfavored due to the increase in order. Water in contact with an organic molecule loses favorable water-water contacts. To compensate, it strengthens its remaining water-water contacts, making them more ice-like. The local water structure becomes more rigid, and the strengths and number of individual water HBs can compensate for the lost HBs due to the presence of the cavity created by the orgnic entity, and may even be entthalpically favorable. Due to the increased ice-like nature of the waters around the organic, the entropy has significantly decreased. Dimer structure; when the two hydrophobic molecules associate, the hydrocarbon surface area exposed to water decreases, diminishing the amount of ice-like water. -> unfavorable enthalpy change or a close-to-zero enthalpy change. But entropically favorable. The net effect is that the TΔS o term outweighs the ΔH o term, producing a favorable ΔG o. Hydrophobic association is entropy driven.

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