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Useful and essential structures can be made by self–assembly. In fact, life–forms were first made poOrganic Chemistry Chemistry Question

Self–assembly

Useful and essential structures can be made by self–assembly. In fact, life–forms were first made possible by the self–assembly of cell membranes about 4 billion years ago. Self–assembly is a fundamental principle that generates structural organization on all scales from molecules to galaxies. Self–assembly is defined as reversible processes in which pre–existing parts or disordered components of a pre–existing system form stable structures of well–defined patterns.

Some transition metal complexes can participate in the self–assembly. For example, a Ni complex with a long alkyl chain can be formed from many separate parts in the following reaction.

18.1.

[VISUAL]

Predict the structure around the Ni(II) cation.

Model Answer

square planar

18.2.

Determine whether A2+ is paramagnetic or not, using the d–orbital splitting pattern of Ni(II) in this structure.

Model Answer

Ni2+, d8, square planar, diamagnetic

18.3.

Indicate the hydrophobic portion in A2+.

Model Answer

a long alkyl side chain: –C16H33.

18.4.

Figure 18.1. The molecular structure for A2+ and the packing structure of A(ClO4)2 ⋅ H2O.

[VISUAL]

What is the driving force for such assembly? (Hint: Its ionic compound, A(ClO4)2⋅H2O, is found to float on the surface of water although its density is greater than 1.0 g cm-3.)

Model Answer

hydrophobicity due to the long alkyl chains

18.5.

Metal complexes of TCNQ (7,7,8,8–tetracyano–p–quinodimethane) have been studied due to magnetic and electric conducting properties.

(TCNQ) = [VISUAL]

The infrared spectrum is diagnostic for the formal oxidation state and the coordinative status of the TCNQ molecules.

For TCNQ as pictured, which bond (among a – e) has the highest vibrational frequency?

Model Answer

bond a

18.6.

Point out the bond(s) (among a – e) which might be shortened when TCNQ is reduced to form the radical anion.

Model Answer

bonds b and d are shortened upon reduction.

18.7.

The TCNQ derivative of A2+ ([A2+(TCNQ)2](TCNQ)⋅(CH3COCH3)) also shows an interesting structural feature as shown in Figure 18–2.

Figure 18.2. The molecular structure for A2+ and the packing structure of [A2+(TCNQ)2](TCNQ⋅CH3COCH3)

[VISUAL]

What is the coordination number for atom Ni in the TCNQ derivative of A2+?

Model Answer

coordination number 6

18.8.

In this structure, TCNQ molecules overlap one another. What is the driving force for such organization?

Model Answer

π – π stacking interactions

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