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Evaluation of intermolecular interactions in thioxanthone derivatives: substituent effect on crystal diversity

dc.contributor.authorJacob, C.
dc.contributor.authorda Piedade, Fátima M.
dc.contributor.authorPaula Robalo, M.
dc.contributor.authorTeresa Duarte, M.
dc.date.accessioned2013-01-31T17:58:18Z
dc.date.available2013-01-31T17:58:18Z
dc.date.issued2011
dc.description.abstractA family of 9H-thioxanthen-9-one derivatives and two precursors, 2-[(4-bromophenyl) sulfanyl]-5-nitrobenzoic acid and 2-[(4-aminophenyl) sulfanyl]-5-nitrobenzoic acid, were synthesized and studied in order to assess the role of the different substituent groups in determining the supramolecular motifs. From our results we can conclude that Etter's rules are obeyed: whenever present the -COOH head to head strong hydrogen bonding dimer, R-2(2)(8) synthon, prevails as the dominant interaction. As for -NH2, the best donor when present also follows the expected hierarchy, an NH center dot center dot center dot O(COOH) was formed in the acid precursor (2) and an NH center dot center dot center dot O(C=O) in the thioxanthone (4). The main role played by weaker hydrogen bonds such as CH center dot center dot center dot O, and other intermolecular interactions, pi-pi and Br center dot center dot center dot O, as well as the geometric restraints of packing patterns shows the energetic interplay governing crystal packing. A common feature is the relation between the p-p stacking and the unit cell dimensions. A new synthon notation, R`, introduced in this paper, refers to the possibility of accounting for intra- and intermolecular interactions into recognizable and recurring aggregate patterns.por
dc.identifier.citationJACOB, C.; da PIEDADE, Fátima M.; ROBALO, M. Paula; DUARTE, M. Teresa - Evaluation of intermolecular interactions in thioxanthone derivatives: substituent effect on crystal diversity. Crystengcomm. ISSN 1466-8033. Vol. 13, n.º7 (2011) 2604-2616.por
dc.identifier.issn1466-8033
dc.identifier.urihttp://hdl.handle.net/10400.21/2152
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherRoyal Soc Chemistrypor
dc.subjectHydrogen-Bond Patternspor
dc.subjectOrganic-Compoundspor
dc.subjectCH/PI Interactionpor
dc.subjectC-Hpor
dc.subjectRecognitionpor
dc.subjectComplexespor
dc.subjectMoleculespor
dc.subjectChemistrypor
dc.subjectDatabasepor
dc.subjectNetworkpor
dc.titleEvaluation of intermolecular interactions in thioxanthone derivatives: substituent effect on crystal diversitypor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.conferencePlaceCambspor
oaire.citation.endPage2616por
oaire.citation.issue7por
oaire.citation.startPage2604por
oaire.citation.titleCrystengcommpor
oaire.citation.volume13por
rcaap.rightsrestrictedAccesspor
rcaap.typearticlepor

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