Anchor Effect on Pedal Motion Observed in Crystal Phase of an Azobenzene Derivative

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dc.authoridKARABIYIK, HASAN/0000-0001-7894-6646
dc.authoridKarabiyik, Hande/0000-0001-6180-2080
dc.authoridAlbayrak kastas, Cigdem/0000-0003-0235-7460
dc.contributor.authorKarabiyik, Hasan
dc.contributor.authorPetek, Hande
dc.contributor.authorIskeleli, Nazan Ocak
dc.contributor.authorAlbayrak, Cigdem
dc.contributor.authorAgar, Erbil
dc.date.accessioned2025-03-23T19:44:16Z
dc.date.available2025-03-23T19:44:16Z
dc.date.issued2011
dc.departmentSinop Üniversitesi
dc.description.abstractSome molecules having a molecular skeleton similar to that of stilbenes and azobenzenes show orientational disorder in the crystals due to pedal motion. Heretofore, the orientational disorder through pedal motion has been observed for the compounds containing only two aromatic rings in the absence of bulky substituent groups. Here we report that the pedal motion can be detected even in the presence of a bulky substituent group to which orientational disorder becomes invisible as a result of anchor effect arising from phenoxyphtalonitrile group. X-ray crystallographic analysis of the compound, C23H18N4O, reveals the existence of partially overlapped two pedal conformers. The compound crystallizes in the monoclinic space group P2(1)/c with a = 12.9429(11) a<<, b = 8.5075(5) a<<, c = 21.063(2) a<< and beta = 123.155(6)A degrees. Major pedal conformer is stabilized by weak C-H center dot center dot center dot O type hydrogen bond and C-H center dot center dot center dot pi type edge-to-face interactions in solid state. Quantum chemical calculations at B3LYP/6-311G+(d,p) level suggest that the stabilization of the compound decreases with increasing deviation from the planar geometry of trans-azobenzene fragment. Molecular and crystal structure of 4-[2-Methyl-4-(4-ethylphenyldiazenyl)]phenoxyphtalonitrile, C23H18N4O, indicate the existence of partially overlapped two pedal conformers in which orientational disorder becomes invisible as a result of anchor effect arising from phenoxyphtalonitrile group.
dc.description.sponsorshipOndokuz Mayis University [F.279, F.377]
dc.description.sponsorshipThe authors wish to acknowledge Ondokuz Mayis University for the use of the STOE IPDS II diffractometer purchased under Grants F.279 and F.377.
dc.identifier.doi10.1007/s10870-011-0152-1
dc.identifier.endpage1648
dc.identifier.issn1074-1542
dc.identifier.issn1572-8854
dc.identifier.issue11
dc.identifier.scopus2-s2.0-80054984644
dc.identifier.scopusqualityQ3
dc.identifier.startpage1642
dc.identifier.urihttps://doi.org/10.1007/s10870-011-0152-1
dc.identifier.urihttps://hdl.handle.net/11486/6916
dc.identifier.volume41
dc.identifier.wosWOS:000295366000007
dc.identifier.wosqualityQ4
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherSpringer/Plenum Publishers
dc.relation.ispartofJournal of Chemical Crystallography
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectPedal motion
dc.subjectAzobenzene
dc.subjectOrientational disorder
dc.subjectConformational interconversion
dc.titleAnchor Effect on Pedal Motion Observed in Crystal Phase of an Azobenzene Derivative
dc.typeArticle

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