Weak Intermolecular Forces, but High Melting Points

Gao, J; Djaidi, D; Marjo, CE; Bhadbhade, MM; Ung, AT; Bishop, R

Weak Intermolecular Forces, but High Melting Points

Gao, J Djaidi, D Marjo, CE Bhadbhade, MM Ung, AT

Bishop, R

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Publication Type:: Journal Article
Citation:: Australian Journal of Chemistry, 2017, 70 (5), pp. 538 - 545
Issue Date:: 2017-01-01

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Field	Value	Language
dc.contributor.author	Gao, J	en_US
dc.contributor.author	Djaidi, D	en_US
dc.contributor.author	Marjo, CE	en_US
dc.contributor.author	Bhadbhade, MM	en_US
dc.contributor.author	Ung, AT https://orcid.org/0000-0002-5665-0702	en_US
dc.contributor.author	Bishop, R	en_US
dc.date.issued	2017-01-01	en_US
dc.identifier.citation	Australian Journal of Chemistry, 2017, 70 (5), pp. 538 - 545	en_US
dc.identifier.issn	0004-9425	en_US
dc.identifier.uri	http://hdl.handle.net/10453/124135
dc.description.abstract	© 2017 CSIRO. The poorly soluble racemic compound 6,6a,13,13a-tetrahydropentaleno[1,2-b:4,5-b′]diquinoline (4) has an exceptionally high melting point range of 352-354°C despite its low molar mass (308.38) and a structure containing only 40 atoms (38 of which are C and H). Analysis of the X-ray crystal structure and Hirshfeld surface of 4, along with comparison with its isostructural homologue 2, reveals how this occurs in the absence of Pauling-type hydrogen bonding. Excellent complementarity between homochiral molecules of 4 allows formation of enantiomerically pure layers using C-Hπ, aromatic ππ, and C-HN interactions. The alternating layers of opposite handedness are then crosslinked by means of aza-1,3-peri hydrogen interactions. This bifurcated C-HNH-C motif acts as a molecular clip creating a highly rigid network structure. The role of weaker intermolecular forces in influencing the solubility and bioavailability of potential drug molecules is discussed in the context of the popular Lipinski 'rule of 5' guidelines.	en_US
dc.relation.ispartof	Australian Journal of Chemistry	en_US
dc.relation.isbasedon	10.1071/CH16565	en_US
dc.subject.classification	General Chemistry	en_US
dc.title	Weak Intermolecular Forces, but High Melting Points	en_US
dc.type	Journal Article
utslib.citation.volume	5	en_US
utslib.citation.volume	70	en_US
utslib.for	0301 Analytical Chemistry	en_US
utslib.for	03 Chemical Sciences	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	closed_access
pubs.issue	5	en_US
pubs.publication-status	Published	en_US
pubs.volume	70	en_US

Abstract:

© 2017 CSIRO. The poorly soluble racemic compound 6,6a,13,13a-tetrahydropentaleno[1,2-b:4,5-b′]diquinoline (4) has an exceptionally high melting point range of 352-354°C despite its low molar mass (308.38) and a structure containing only 40 atoms (38 of which are C and H). Analysis of the X-ray crystal structure and Hirshfeld surface of 4, along with comparison with its isostructural homologue 2, reveals how this occurs in the absence of Pauling-type hydrogen bonding. Excellent complementarity between homochiral molecules of 4 allows formation of enantiomerically pure layers using C-Hπ, aromatic ππ, and C-HN interactions. The alternating layers of opposite handedness are then crosslinked by means of aza-1,3-peri hydrogen interactions. This bifurcated C-HNH-C motif acts as a molecular clip creating a highly rigid network structure. The role of weaker intermolecular forces in influencing the solubility and bioavailability of potential drug molecules is discussed in the context of the popular Lipinski 'rule of 5' guidelines.

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http://hdl.handle.net/10453/124135