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PMP-102 > Physical properties, analytical chemistry, purity determination and compounds separation > Flashcards

Physical properties, analytical chemistry, purity determination and compounds separation Flashcards

1
Q

Physical property

A

characteristic of matter that can be measured or observed without a change in its chemical composition

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2
Q

Examples of physical properties:

A

colour, hardness, mass, volume, malleability, solubility, electrical conductivity, density, lipophilicity, melting point, boiling point

flammability, toxicity, acidity (pH), reactivity (many types), heat of combustion

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3
Q

Intensive properties

A

not depend on the amount of substance (i.e. temperature)

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4
Q

Extensive properties

A

depend on the amount of substance (i.e. mass, volume)

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5
Q

Chemical property

A

can be measured by changing the chemical composition of a substance

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6
Q

Physical states

A

amorphous solid, crystalline solid, hygroscopic solid, liquid or gas

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7
Q

Intermolecular forces

A

attraction forces between molecules (non-bonding)

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8
Q

1) Dipole-dipole interactions

A

interactions between the positive end of one dipole and the negative end of another dipole

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9
Q

2) van der Waals Forces

A

relatively weak forces of attraction that exist between nonpolar molecules. Distance-dependent interactions. Called induced dipole–induced dipole interactions.

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10
Q

3) Hydrogen bonding

A

attractive force between the H attached to an electronegative atom of one molecule and an electronegative atom of the same (intramolecular) or a different molecule (intermolecular). i.e. H2O

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11
Q

Melting point (mp)

A

temperature at which a solid becomes a liquid

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12
Q

Melting point H2O (ice point)

A

at 1 atm is 0 °C (32 °F, 273.15 K)

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13
Q

Characterise organic compounds and confirm their _____

A

purity

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14
Q

mp pure compound

A

always higher than the mp of an impure compound

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15
Q

Increases as the molecular weight _____

A

increases

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16
Q

Packing:

A

how well the individual molecules in a solid fit together in a crystal lattice (symmetrical three-dimensional arrangement of atoms inside a crystal).

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17
Q

The _____ the crystal lattice, the _____ energy is required to break it and eventually melt the compound

A

tighter
more

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18
Q

Boiling point (bp)

A

temperature at which the vapour pressure of the liquid is equal to the atmospheric pressure. Temperature at which a substance can change its state from a liquid to a gas at a given pressure

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19
Q

Strongly influenced by intermolecular forces
bp increases as the molecular size _____

A

increases

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20
Q

What are the factors of VDW forces

A

area of contact between the molecules

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21
Q

the _____ the area of contact, the ______ are the van der Waals forces

A

greater
stronger

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22
Q

the ______ the amount of energy required to ______ these forces

A

greater
overcome

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23
Q

Branched alkane has

A

more compact, less surface area for force interactions. Boils at a lower temperature

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24
Q

Hydrogen bonding

A

OH hydrogen → strongly polarised → H-bond with a pair of nonbonding electrons from the O of another alcohol molecule increasing bp

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25
Q

Dipole–dipole attractions

A

polarised C-O and H-O bonds and the nonbonding electrons produce a dipole moment of 1.69 D in ethanol, compared with a dipole moment of only 0.08 D in propane

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26
Q

H-bonds

A

clearly much stronger intermolecular attractions than dipole–dipole attractions

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27
Q

Carboxylic acids high bp:

A

Carboxylic acids high bp:

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28
Q

H2O: high polar solvent

A

excellent solvent for polar and ionic molecules
poor solvent for nonpolar molecules

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29
Q

Hydrophilicity or lipophobicity?

A

ability of a chemical compound or drug to go into solution in H2O and polar solvents (e.g. MeOH) and have “fear of the fat “.

Hydrophilic or lipophobic molecule are polar or ionic, forms H-bonds and
dipole-dipole with solvent, fat insoluble, cannot cross cell membrane,
bind to receptor molecules on the outer surface of target cells

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30
Q

Biological membranes are

A

lipophilic and the rate of drug transfer for passively absorbed drugs is directly related to the lipophilicity of the molecule

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31
Q

µ=𝛿 x d
What is this equation used for? and what does each letter mean?

A

Bond polarity and bond dipole moments
𝛿 = amount of charge
d = distance between of charges

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32
Q

Polarity of a molecule

A

indicated by the molecular dipole moment of the entire molecule

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33
Q

Molecular dipole moment of a molecule

A

equal to the vector sum (sign is important) of the all individual bond dipole moments

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34
Q

Solubility

A

amount of a solute that can be dissolved in a specific solvent under given conditions.

Measure of how much of the solute can be dissolved into the solvent at a specific temp

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35
Q

“Like dissolves like.”

A

Polar substances dissolve in polar solvents, and
nonpolar substances dissolve in nonpolar solvents

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36
Q

1) Polar Solute in a Polar Solvent (Dissolves)

A

The process of dissolving solute in solvent is called solvation, or hydration when the solvent is H2O

H2O molecules surround each ion, with the appropriate end of the dipole moment next to the ion

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37
Q

2) Polar Solute in a Nonpolar Solvent (Does Not Dissolve)

A

Nonpolar molecules (no partial charges) do not solvate ions very strongly.

Attractions of the ions in the solid for each other are much greater than their attractions for the solvent

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38
Q

3) Nonpolar Solute in a Nonpolar Solvent (Dissolves)

A

Molecules of a nonpolar substance: weakly attracted to each other, and these van der Waals attractions are easily overcome by van der Waals attractions with the solvent

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39
Q

4) Nonpolar Solute in a Polar Solvent (Does Not Dissolve)

A

Nonpolar molecules: weakly attracted to each other, and little energy is required to separate them.

H2O molecules: strongly attracted to each other by their hydrogen bonding

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40
Q

“Like dissolves like also applies to the mixing of liquids. “

A
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41
Q

What is immiscible?

A

do not mix! NONPOLAR
e.g. H2O and gasoline (or oil)

42
Q

Miscible liquids are POLAR molecules

A

Ethyl alcohol and H2O

43
Q

n-hexane and dodecane: miscible in one another because….

A

they are nonpolar - not miceable TOGETHER

44
Q

Partition coefficient

A

Substance added to a pair of immiscible solvents → distributes itself between the two solvents according to its affinity for each phase (solvent)

45
Q

aqueous or polar phase is a…..

A

Polar compound (e.g. ionised drug or amino acids):

46
Q

non-aqueous or organic phase is a….

A

Non-polar compound (e.g. non-ionised drug):

47
Q

Partition law:

A

a given substance, at a given temperature, will partition itself between two immiscible solvents in a constant ratio of concentrations’.

48
Q

Partition coefficient P= [ _____ / _____ ]

A

[organic]/ [aqueous]

49
Q

Predict ADE of drugs within the body

A

Predict the onset of action of drugs or the duration of action of drugs

50
Q

What is Drug design?

A

used in mathematical equations that try to relate the biological activity of a drug to its physical and chemical characteristics (QSAR)

51
Q

Chemistry laboratory:

A

separate, purify or extract compounds

52
Q

Calculation =
Consider the distribution of 100 mg of a drug between 50 mL of an organic solvent and 50 mL of H2O

In a separating funnel;

66.7mg (2) {unionised } ORGANIC 50ml <> 33.3mg (1) {unionied} WATER 50ml

A

a) organic]= 66.7/50 = 1.33 mg mL-1
[water]= 33.3/50 = 0.67 mg mL-1

b) P=[organic]/[aqueous]=1.33 mg mL-1/0.67 mg mL-1=2

c) % of drug extracted: simply the mass of drug in the organic phase divided by the total mass of drug, i.e. 66.7/100 x 100= 66.7%.

53
Q

Weak acid or weak base

A

ionisation to form an anion or a cation alters the solubility profile of the drug

54
Q

Partition coefficient depends;

A

vary depending on the pH at which the measurement is carried out

55
Q

1] Adjust the experimental conditions;

A

measure P of the unionised molecule
P value for acids: measured at low pH when the acid is unionised

P value for bases: measured at high pH to prevent ionisation

56
Q

2] Apparent partition coefficient (Papp)=

A

Ptrue x funionised

57
Q

Ptrue:

A

true partition coefficient of the unionised species

58
Q

Papp :

A

dependent on the proportion of substance present in solution, which in turn depends upon the pH of the solution

59
Q

if funionised=1 Papp = Ptrue and the compound is ______

A

UNIONISED

60
Q

shake flask method =

A

logP=[organic]/[aqueous]

e.g. 1-Octanol: results obtained seem to correlate best with biological data obtained in vivo.

61
Q

Hydrophobic/ hydrophilic =

A

aqueous buffer (pH 7.4) = represents aqueous compartments within the body, e.g. blood plasma.

62
Q

Partition coefficient step by step ( list 4 steps)

A
  1. The two phases are mixed
  2. Two phases separate→ the drug is added (flask shaken)
  3. Two phases allowed to separate → concentration of drug in the aqueous phase is then determined (titration, spectrometry).
  4. Concentration in the octanol phase: found by subtraction and the value of P is calculated.
63
Q

Separation

A

purification of mixtures

64
Q

Side-reactions and by-products is a results of

A

Incomplete chemical reaction

65
Q

Drugs isolation from complex mixtures of chemicals e.g.

A

isolation of a drug metabolite from a blood or urine sample

66
Q

Non-ionised

A

dissolve well in non-polar organic solvents (diethyl ether, chloroform or ethyl acetate)

67
Q

Ionised acids (conjugated base-e.g.

A

COO-) and bases (conjugate acid-NH3+): more soluble in aqueous solvents (water or buffer)

68
Q

Acidic molecules:

A

Soluble in organic solvents at low pH (unionised)
Soluble in polar solvents at high pH.

69
Q

Basic molecules:

A

soluble in organic solvents when the pH is high (unionised)
Soluble in water at low values of pH

70
Q

Separation: if our compound is not pure after partition

Is a purification required?

A

Yes

71
Q

Purification

A

if our compound is pure after partition (solids and liquids)

72
Q

Recrystallisation

A

Procedure for purifying an impure compound in a solvent (solids only).
Based on the principle that the solubility of most solids increases with increased temperature

73
Q

If your compound A is contaminated of compound B, we use a solvent in which:

A

A: not soluble at room temperature (25˚C) but it is soluble in the hot solvent

B: soluble (or partially soluble) at room temperature and when the solvent is hot

A+B= adding hot solvent, A and B go in solution.
Solvent cool down: A is not soluble anymore and crystallises out pure. B stays in solution and does not precipitate back

74
Q

Hot solvent > cooling > filtration =

A

pure compound A

75
Q

Distillation

A

A process where liquids are converted into vapours by heating and followed by condensation of vapours through cooling

76
Q

Non-volatile impurities from volatile liquid
= Mixtures with liquids having a difference in

A

boiling point

77
Q

Explain what Chromatography is:

A

“Methods for separating a mixture into its components, which may also involve identify the components and measuring their concentration”

78
Q

Partition coefficient P (K)=[

A

[solute phase 1]/[solute phase 2]

79
Q

Mobile Phase flows through or over the stationary phase

A

Mobile Phase: gas or liquid

Stationary Phase: solid or liquid supported on a solid

80
Q

Component of a mixture interact differently with the stationary phase →

A

move at different speeds and become separated as they pass down the column

81
Q

Qualitative Chromatography: step by step

A
  • thin layer of absorbent coating of SiO2 or Al2O3 *

1] TLC plate is prepared with a thin layer of absorbent coating

2] Small amount of the sample in solution is spotted on the plate

3] The end of the TLC plate is immersed in a pool of solvent

82
Q

4] Out in a glass gar secured tightly with a lid

A

a) put chromatography paper in solvent BUT the line above surface of solvent
b) solvent rises up by caplillarity

83
Q

Retention factor Rf= b/a

A

b = distance travelled by sample
a = distance travelled by solvent

84
Q

What to use if compounds are colourless?

A

Fluorescence: stationary phase has a substance added which will fluoresce when exposed to UV light

85
Q

Using fluorescence:

A
  • No UV light: cannot see compounds
  • Plate all glow apart from where the spots are. The spots show up as darker patches because they mask the glow
  • Make the spots visible by reacting with something which produces a coloured product
86
Q

Stationary Phase =
Free OH groups: can form hydrogen bonds, van der Waals forces and dipole-dipole attractions.
Very polar surface

A

More polar compounds = form H-bonds with silica → stick to the silica gel more firmly than the others. Adsorbed more strongly

87
Q

Less polar compounds:

A

form only weak van der Waals interactions → stick less to the silica gel → more carried by the mobile phase

88
Q

More strongly a compound is adsorbed (more polar is) →

A

less distance travelled up the plate. Low polarity compounds have higher Rf values (run more) than higher polarity compounds.

89
Q

Mobile Phase

A

Ability to dissolve: solubility of compounds (Like dissolves like) in mobile phase influence how fast they move up the TLC plate.

The more soluble they are, the faster they move.

Polar compounds: run faster in polar solvent
Non-polar compounds: run faster in non-polar solvents

Ability to be adsorbed on the silica: affinity for the silica. Can displace the compounds “pushing” them up the plate.

Solvent too strongly adsorbed: fully displaces all compounds →they move up the plate together with the solvent front with no separation

Solvent too weakly adsorbed: its solvating power alone may be insufficient to move any compounds fast enough to effect separation

90
Q

Separation - mobile phase to stationary phase

A

Less eluting strength (less polar solvents)

MOBILE PHASE&raquo_space;>

Greatest Eluting strength (more polar solvents)

Less strongly adsorbed (less polar compounds)

Stationary Phase&raquo_space;>

Most strongly Absorbed

91
Q

Absorptivity of compounds:

A

increases with increased polarity (i.e. the more polar the compound then the stronger it binds to the silica)

92
Q

Eluting power of solvents

A

increases with polarity

Low polarity compounds →eluted with low polarity solvents
Higher polarity compounds → solvents of higher polarity.
Solvents can be mixed together

93
Q

The stronger a compound is bound to the silica , the _____ it moves up

A

slower

94
Q

Non-polar compounds: move up the plate most ______ (higher Rf value)

A

rapidly

95
Q

Polar compounds: travel up the TLC plate _____ or not at all (lower Rf value)

A

slowly

96
Q

Column chromatography: purification method (solids and liquids)

A

Same principles of TLC:
Non-polar compounds: move down rapidly: will come out first from column
Polar compounds: travel down slowly or not at all: will come out very late or will stay in the column

Solvent collected in small fractions containing the pure compound

97
Q

Gradient elution:

A

change the proportion of the solvents over a pre-determined timescale (i.e. 100% hexane, then 90 hexane: 10 ethyl acetate, etc

98
Q

Analytical Chemistry

A

Deals with obtaining, processing, and presenting both the qualitative (which substances are in a sample?) and quantitative (how much?) data of substances

99
Q

Analytical Chemistry

A

Deals with obtaining, processing, and presenting both the qualitative (which substances are in a sample?) and quantitative (how much?) data of substances

100
Q

Melting point and boiling point:

A

any pure substance will have a specific melting and boiling point. Presence of impurities will cause a lower melting point as well as a change in boiling point

101
Q

Purity determination = TLC

A

if your substance is pure (no impurities present), you should see only one spot in your plate after a run

102
Q

More advanced light-based or spectroscopic methods:

A

UV-VIS spectroscopy, nuclear magnetic resonance (NMR) and infrared spectroscopy (IR). Other methods used in testing the purity include mass spectroscopy, capillary electrophoresis, optical rotation, HPLC and particle size analysis

PMP-102 (49 decks)

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