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Synergistic effects in clathrate selectivity
Author(s)
Sayed, Amina
Date Issued
2012
Type
Thesis
Publisher
Cape Peninsula University of Technology
Abstract
The inclusion behaviour of a series of hydroxyl hosts with a variety of liquid guests has been
investigated. The host 9-(4-methoxyphenyl)-9H-xanthen-9-ol (A1), C20H16O3, forms
inclusion compounds with aniline (ANI), 3-picoline (3PIC), morpholine (MORPH), Nmethylacetamide
(NMA) and N-methylformamide (NMF). Their structures have been
elucidated and correlated with their thermal behaviour. The inclusion compounds A1ANI
and A1MORPH were successfully solved in space group P21/c, whereas A13PIC was
solved in 𝑃ī. Non-isothermal kinetics of desolvation were performed for A13PIC and
A1MORPH. The packing of A13PIC and A1MORPH is characterized by (Host)(Guest)
hydrogen bonds, whereas A1ANI is stabilised by (Host)(Host) hydrogen bonding. Three
structures were obtained for the host A1 and the guest N-methylacetamide, with structural
formulas of C20H16O3
C3H7NO (A1NMA), C20H16O3
2C3H7NO (A12NMA) and
2C20H16O3
2C3H7NO (2A12NMA). The packing of A1NMA, A12NMA and 2A12NMA
are characterized by (Host)-OHO-(Guest) and (Guest)-NHO-(Guest) hydrogen bonds,
which gave hydrogen bonding patterns of 𝐶2
2(7), 𝐶3
3(11) and 𝐶4
2(11) respectively. The hydrate
A1NMFH2O was successfully solved in the triclinic space group 𝑃ī. The A1NMFH2O
hydrogen bond pattern may be described according to Etter’s notation as 𝑅4
2(8) and 𝑅6
6(16).
The host 9-(3-methoxyphenyl)-9H-xanthen-9-ol (A2), C20H16O3, forms inclusion compounds
with morpholine (A2MORPH), N-methylacetamide (A2NMA) and N-methylformamide
(A2NMF), with host-guest ratios 1:1. The crystal structure of the apohost was solved in Pbca
with Z=8. The structures of A2MORPH and A2NMF were solved in 𝑃ī, whereas A2NMA
was solved in P21/n. The packing of these structures is stabilised by (Host)(Guest)
hydrogen bonds.
The host 5-(4-methoxyphenyl)-5H-dibenzo[a,d]cyclohepten-5-ol (A26), C22H18O2, forms
inclusion compounds with aniline (A26ANI) and morpholine (A26MORPH). A26MORPH
and A26ANI crystallised in the space groups Pc and 𝑃ī respectively. The packing of these
structures are characterized by (Host)-OHO-(Host) hydrogen bonding. A guest exchange
reaction was performed.
The host compounds 5-(4-chlorophenyl)-5H-dibenzo[a,d]cyclohepten-5-ol (C21H15OCl),
5-[3(trifluoromethyl)phenyl]-5H-dibenzo[a,d]cyclohepten-5-ol (C22H15OF3) and
5-(naphthalen-1-yl)-5H-dibenzo[a,d]cyclohepten-5-ol (C25H18O) form inclusion compounds
with morpholine. All three structures were solved in 𝑃ī with the host molecules hydrogen
bonded to the morpholine guests.
investigated. The host 9-(4-methoxyphenyl)-9H-xanthen-9-ol (A1), C20H16O3, forms
inclusion compounds with aniline (ANI), 3-picoline (3PIC), morpholine (MORPH), Nmethylacetamide
(NMA) and N-methylformamide (NMF). Their structures have been
elucidated and correlated with their thermal behaviour. The inclusion compounds A1ANI
and A1MORPH were successfully solved in space group P21/c, whereas A13PIC was
solved in 𝑃ī. Non-isothermal kinetics of desolvation were performed for A13PIC and
A1MORPH. The packing of A13PIC and A1MORPH is characterized by (Host)(Guest)
hydrogen bonds, whereas A1ANI is stabilised by (Host)(Host) hydrogen bonding. Three
structures were obtained for the host A1 and the guest N-methylacetamide, with structural
formulas of C20H16O3
C3H7NO (A1NMA), C20H16O3
2C3H7NO (A12NMA) and
2C20H16O3
2C3H7NO (2A12NMA). The packing of A1NMA, A12NMA and 2A12NMA
are characterized by (Host)-OHO-(Guest) and (Guest)-NHO-(Guest) hydrogen bonds,
which gave hydrogen bonding patterns of 𝐶2
2(7), 𝐶3
3(11) and 𝐶4
2(11) respectively. The hydrate
A1NMFH2O was successfully solved in the triclinic space group 𝑃ī. The A1NMFH2O
hydrogen bond pattern may be described according to Etter’s notation as 𝑅4
2(8) and 𝑅6
6(16).
The host 9-(3-methoxyphenyl)-9H-xanthen-9-ol (A2), C20H16O3, forms inclusion compounds
with morpholine (A2MORPH), N-methylacetamide (A2NMA) and N-methylformamide
(A2NMF), with host-guest ratios 1:1. The crystal structure of the apohost was solved in Pbca
with Z=8. The structures of A2MORPH and A2NMF were solved in 𝑃ī, whereas A2NMA
was solved in P21/n. The packing of these structures is stabilised by (Host)(Guest)
hydrogen bonds.
The host 5-(4-methoxyphenyl)-5H-dibenzo[a,d]cyclohepten-5-ol (A26), C22H18O2, forms
inclusion compounds with aniline (A26ANI) and morpholine (A26MORPH). A26MORPH
and A26ANI crystallised in the space groups Pc and 𝑃ī respectively. The packing of these
structures are characterized by (Host)-OHO-(Host) hydrogen bonding. A guest exchange
reaction was performed.
The host compounds 5-(4-chlorophenyl)-5H-dibenzo[a,d]cyclohepten-5-ol (C21H15OCl),
5-[3(trifluoromethyl)phenyl]-5H-dibenzo[a,d]cyclohepten-5-ol (C22H15OF3) and
5-(naphthalen-1-yl)-5H-dibenzo[a,d]cyclohepten-5-ol (C25H18O) form inclusion compounds
with morpholine. All three structures were solved in 𝑃ī with the host molecules hydrogen
bonded to the morpholine guests.
Additional information
Thesis (MTech (Chemistry))-- Cape Peninsula University Technology, 2012
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