Crystallographic and conformational analysis of two novel trans-azo benzene compounds

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dc.authoridKarabiyik, Hande/0000-0001-6180-2080
dc.authoridKARABIYIK, HASAN/0000-0001-7894-6646
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.date.accessioned2025-03-23T19:44:03Z
dc.date.available2025-03-23T19:44:03Z
dc.date.issued2009
dc.departmentSinop Üniversitesi
dc.description.abstractThe molecular and crystal structure of (E)-2-Acetyl-4-(2-bromophenyldiazenyl)phenol (1) and (E)-2-Methyl-4-(o-tolyldiazenyl)phenol (2) were characterized and determined by single crystal X-ray diffraction method besides spectroscopic means. The periodic organization of 1 is stabilized by C-H center dot center dot center dot O type weak H-bond and Br center dot center dot center dot O type weak halogen bonding and thus, a two dimensional puckered network is established almost parallel to 10((1) over bar) the plane. Molecules of 2 are linked into C(7) chains generated by translation along the [1 0 1] direction with the aid of O-H center dot center dot center dot N type H-bonds, and these chains are strengthened by C-H center dot center dot center dot pi interactions involving o-tolylphenol ring. Quantum chemical studies at B3LYP/6-311 ++G(d,p) level reveal that potential barrier of the compounds around Ar-N torsions is of double minimum character unless it is defected by the presence of o-substituent groups in the vicinity of the azo bridge. The results from crystallographic and quantum chemical studies suggest that azo benzene compounds may adapt non-planar geometry apart from the most stable planar conformation, which is located on the secondary minima of double potential barrier regarding rotational motion around Ar-N bonds.
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 2 diffractometer purchased under grants F.279 and F.377.
dc.identifier.doi10.1007/s11224-009-9490-4
dc.identifier.endpage910
dc.identifier.issn1040-0400
dc.identifier.issn1572-9001
dc.identifier.issue5
dc.identifier.scopus2-s2.0-70349883689
dc.identifier.scopusqualityQ2
dc.identifier.startpage903
dc.identifier.urihttps://doi.org/10.1007/s11224-009-9490-4
dc.identifier.urihttps://hdl.handle.net/11486/6857
dc.identifier.volume20
dc.identifier.wosWOS:000268773900020
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherSpringer/Plenum Publishers
dc.relation.ispartofStructural Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectAzo benzene
dc.subjectDFT/B3LYP
dc.subjectConformational analysis
dc.subjectCrystal structure
dc.titleCrystallographic and conformational analysis of two novel trans-azo benzene compounds
dc.typeArticle

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