A chalcone showing positional disorder, two related diarylcyclohexenones showing enantiomeric disorder and a related hydroxyterphenyl, all derived from simple carbonyl precursors

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dc.authoridSalian, Vinutha/0000-0002-4990-0806
dc.authoridERSANLI, CEM CUNEYT/0000-0002-8113-5091
dc.authoridAkkurt, Mehmet/0000-0003-2421-0929
dc.authoridCELIK, OMER/0000-0003-2633-4458
dc.authoridCelik, Omer/0000-0002-3314-6132
dc.contributor.authorSalian, Vinutha V.
dc.contributor.authorNarayana, Badiadka
dc.contributor.authorYathirajan, Hemmige S.
dc.contributor.authorAkkurt, Mehmet
dc.contributor.authorCelik, Omer
dc.contributor.authorErsanli, Cem Cuneyt
dc.contributor.authorGlidewell, Christopher
dc.date.accessioned2025-03-23T19:32:13Z
dc.date.available2025-03-23T19:32:13Z
dc.date.issued2015
dc.departmentSinop Üniversitesi
dc.description.abstractFour compounds are reported, all of which lie along a versatile reaction pathway which leads from simple carbonyl compounds to terphenyls. (2E)-1-(2,4- Dichlorophenyl)-3-[4-(prop-1-en-2-yl)phenyl]prop-2-en-1-one, C18H14Cl2O, (I), prepared from 4-(prop-1-en-2-yl)benzaldehyde and 2,4-dichloroacetophenone, exhibits disorder over two sets of atomic sites having occupancies of 0.664 (6) and 0.336 (6). The related chalcone (2E)-3-(4-chlorophenyl)-1-(4-fluorophenyl)-prop-2-en-1-one reacts with acetone to produce (5RS)-3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]cyclohex-2-en-1-one, C21H21ClO, (II), which exhibits enantiomeric disorder with occupancies at the reference site of 0.662 (4) and 0.338 (4) for the (5R) and (5S) forms; the same chalcone reacts with methyl 3-oxobutanoate to give methyl (1RS, 6SR)-4-(4-chlorophenyl)-6-[4-(propan-2-yl)phenyl]-2-oxocyclohex-3-ene-1-carboxylate, C23H23ClO3, (III), where the reference site contains both (1R,6S) and (1S,6R) forms with occupancies of 0.923 (3) and 0.077 (3), respectively. Oxidation, using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, of ethyl (1RS, 6SR)-6-(4-bromophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate, prepared in a similar manner to (II) and (III), produces ethyl 4 ''-bromo-4-fluoro-5'-hydroxy-1,1':3',1 ''-terphenyl-4'-carboxylate, C21H16BrFO3, (IV), which crystallizes with Z' = 2 in the space group P (1) over bar. There are no significant intermolecular interactions in the structures of compounds (I) and (II), but for the major disorder component of compound (III), the molecules are linked into sheets by a combination of C-H center dot center dot center dot O and C-H center dot center dot center dot pi(arene) hydrogen bonds. The two independent molecules of compound (IV) form two different centrosymmetric dimers, one built from inversion-related pairs of C-H center dot center dot center dot O hydrogen bonds and the other from inversion-related pairs of C-H center dot center dot center dot pi(arene) hydrogen bonds. Comparisons are made with related compounds.
dc.description.sponsorshipUGC through a BSR
dc.description.sponsorshipThe authors are indebted to the X-ray Laboratory of Dicle University Scientific and Technological Applied and Research Center, Diyarbakir, Turkey, for use of the X-ray diffractometer. BN acknowledges the financial assistance of UGC through a BSR one-time grant for the purchase of chemicals and VVS thanks Mangalore University for the provision of research facilities.
dc.identifier.doi10.1107/S2053229615011961
dc.identifier.endpage+
dc.identifier.issn2053-2296
dc.identifier.pmid26146401
dc.identifier.scopus2-s2.0-84937440614
dc.identifier.scopusqualityN/A
dc.identifier.startpage610
dc.identifier.urihttps://doi.org/10.1107/S2053229615011961
dc.identifier.urihttps://hdl.handle.net/11486/5445
dc.identifier.volume71
dc.identifier.wosWOS:000357602800016
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherInt Union Crystallography
dc.relation.ispartofActa Crystallographica Section C-Structural Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectchalcones
dc.subjectdiarylcyclohexenones
dc.subjectterphenyls
dc.subjectcrystal structure
dc.subjectsupramolecular aggregation
dc.subjectenantiomeric disorder
dc.subjecthydrogen bonding
dc.titleA chalcone showing positional disorder, two related diarylcyclohexenones showing enantiomeric disorder and a related hydroxyterphenyl, all derived from simple carbonyl precursors
dc.typeArticle

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