5/8/2018 A Quick Introduction to Supramolecular Chemistry

What is supramolecular chemistry?

Supramolecular chemistry has been defined as...

Your Answer: The study of large molecules 

The correct answer was Chemistry beyond the molecule

While it is true that supramolecules are generally large, it is not

necessarily true that all supramolecules are. Supramolecular
chemistry is primarily concerned with the intermolecular forces
between specific molecules. It is said that molecules are to
supramolecules as atoms are to molecules.

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2. Who started it all off?

When asked who the forefathers of supramolecular chemistry

are/were, which of these would a supramolecular chemist be very
unlikely to name?

Your Answer: Charles Pedersen 

The correct answer was George Wittig

In 1987 Lehn, Pedersen and Cram were honoured with a Nobel

Prize for chemistry due to their work in the field of
supramolecular chemistry. If the name Wittig rings a bell then it
is probably due to the Wittig Reaction, a popular reaction in
undergraduate teaching. Indeed, Wittig was also a Nobel Prize
winner in chemistry with Herbert Brown for their work on boron
and phosphorus chemistry.

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3. So what's it all about?

Supramolecular chemistry is primarily concerned with...

Your Answer: Non-covalent bonding 

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"Traditional organic chemistry" is mainly making and breaking

covalent bonds to form new molecules and this is where
supramolecular chemistry departs from this discipline.
Supramolecular chemistry uses non-covalent forces to achieve
the formation of new supramolecules from molecules. However,
that is not to say that there is an absence of covalent bonding
in supramolecular structures, merely that the non-covalent
bonds are what binds the molecules present together and
hence in essence, transforms a collection of molecules into a
supramolecule.

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4. What does a supramolecule look like, anyway?

Supramolecules are very common in nature, which of the following is

an example of a supramolecule?

Your Answer: DNA 

The DNA double helix is a very good example of a

supramolecule. The hydrogen bonding present is the primary
method by which the two strands are held together and the
structure of each base provides an ideal match for only one of
the four bases. This is the basis for the recording of genetic
information that DNA is known for.

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5. Are there any things you need to consider when making a

supramolecule?

Preorganisation is the term that refers to fixing or limiting the

geometry of a molecule/s to assist in their binding.

Your Answer: True 

There is an entropic price to pay if molecules require

rearrangement to the correct geometry for binding. An example
of this rearrangement is when a bond needs to be rotated to
allow proper access to a lone pair for hydrogen bonding. If the
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lone pair can be fixed in the correct geometry on synthesis, by

making the molecule aromatic and hence with no free rotation
about bonds for example, then this decreases or eliminates the
entropic penalty for reorganising the molecule to the correct
geometry for binding from the geometry adopted when free.
This is just one of the ways that binding affinity can be
increased.

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6. What kind of forces are used in binding?

Van der Waal's forces are insignificant in supramolecular chemistry

due to the fact that they are very weak.

Your Answer: False 

While it is true that Van der Waal's forces are very weak, there is
still often a large component from them due to the sheer
number of Van der Waal's interactions present, particularly with
large molecules. However, the non-directional nature of Van der
Waal's forces makes them very difficult to utilise when
attempting to design an artificial supramolecule.

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7. What can a supramolecule do?

Using the appropriate supramolecular host, it is possible to bind

which of these guests?

Your Answer: All of these 

Cations can generally be bound fairly effectively by ion-dipole

interactions as well as hydrogen bonding. The same principles
can be applied to anions, although this is an area which has
been less extensively studied. It is even possible to bind a
zwitterionic (both positively and negatively charged) guest by
designing two separate domains in the host to bind both types
of charge, this ditopic receptor is much more difficult to design
however, as effectively you must design two binding sites and
find an appropriate way of linking them. The binding of neutral
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species usually relies on non-electrostatic interactions, such as

pi-pi stacking and hydrogen bonding.

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8. So what is a "suitable" host?

What type of guest would a crown ether (essentially a cyclic poly

ether) be able to bind?

Your Answer: Anions 

The correct answer was Cations

Crown ethers (developed by Pedersen) are good binders of

metal cations, e.g. K+. The oxygen atoms form electrostatic
interactions with the cation, holding it in place in the middle of
the ring. There is a degree of size selectivity here, i.e. 18-crown-
6 (a ring with 18 atoms, 6 of which are oxygens) binds K+ much
more strongly than any of the other alkali metals due to the fact
that K+ is the best 'fit' in the ring.

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9. Where's this all going?

There is a lot of interest in the area of supramolecular catalysis at the

moment, why is this?

Your Answer: It would allow very efficient and stereoselective

catalysis of often very difficult reactions. 

A supramolecular catalyst would be capable of bringing the two

(or more) reactants into such close proximity and in the correct
geometry (thereby reducing the activation energy of the
process) so as to facilitate the reaction. In reactions where there
is more than one outcome, in terms of stereochemistry, the
binding of the reactants may block attack to particular sides of
the molecule or make a particular geometry of either a product
or intermediate much more favourable. An example of this
would be blocking attack on one side of a double bond and so
limiting the product to the Z isomer, where under non-catalysed
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circumstances the outcome would be a racemic mixture.

While supramolecular catalysts may be capable of replacing

metal catalysts these supramolecular catalysts, due to their
complexity, would be unlikely to be cheaper than all but the
most expensive metals. Metal catalysed reactions are also very
efficient, palladium catalysed cross couplings, for example, are
known to produce almost 100% isomerically pure products. To
improve upon these would be nigh on impossible! However it
may be possible to improve upon other, less efficient reactions.

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10. Last one...

The 'lock-and-key' principle states that it is possible to bind any guest

if the host is big enough.

Your Answer: True 

The correct answer was f

The lock and key principle actually states that in order for
effective and selective binding to take place the size, shape and
position of a binding site/s in a host is ideal for a specific guest.
This principle is often seen in nature, where the active site of an
enzyme is exactly the right size, shape and position to easily
bind the correct substrate. In fact the active site of an enzyme is
often so well designed that very few other molecules, if any, will
fit in the active site suitably for binding. The same is true for
receptors and this gives rise to the challenge in designing novel
drugs.

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