The role of functional nitro and cyano groups in the self‐assembly of 1,3‐dithiole‐2‐thione–halogen adducts

Skabara, Peter J.; Kanibolotsky, Alexander L.; Render, Simon; Berridge, Rory; Crouch, David J.; Bricklebank, Neil; Coles, Simon J.; Gelbrich, Thomas; Hursthouse, Michael B.

doi:10.1002/hc.20327

Cited by 6 publications

(3 citation statements)

References 19 publications

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“…Raman active vibrations have been selected on the basis of intensity calculations (Maschio et al, 2013), characteristic modes have been assigned to I-I vibrations from the analysis of atomic displacements (Hanson, 2010). For the series of considered compounds, the calculated and experimental wavenumbers (Abate et al, 2010;Antoniadis et al, 2003;Bailey et al, 1997;Congeduti et al, 2000;Nour et al, 1986;Skabara et al, 2007;Yushina et al, 2015;Yushina et al, 2016) are listed in Table S2.…”

Section: Calculationsmentioning

confidence: 99%

“…For this purpose we will compare the advantages and deficiencies of the functions L(r) = Àr 2 (r), (r) and P(r) applied to crystalline organic polyiodides with IÁ Á ÁI halogen bonds. The series of organic polyiodides: NUTSOL (Abate et al, 2010), NUTSUR (Abate et al, 2010), DULZOZ01 (Filgueiras et al, 2001), YUSYUH (Nelyubina et al, 2010), the crystalline I 2 (Bertolotti et al, 2014) and the electrically neutral crystalline complexes with I 2 : HAFLAC (Antoniadis et al, 2003), NULBUR (Bailey et al, 1997), TIJLUU (Skabara et al, 2007) from the Cambridge Structural Database (Groom et al, 2016) have been examined and are listed in Table S1 of the supporting information. We have also taken advantage of our observations of chalcogenazolo(ino)quinolinium polyiodides with IÁ Á ÁI halogen bonds, which have been synthesized and analysed in our group: QIRZEY (Batalov et al, 2013), ZOJPAR (Batalov et al, 2014), DOWMAF (Bartashevich, Yushina, Vershinina et al, 2014), DOWMEJ (Bartashevich, Yushina, Vershinina et al, 2014), SUFLUC (Bartashevich, Nasibullina et al, 2016;Slepukhin, 2015), EJUPOQ (Bartashevich, and IVOVOG .…”

Section: Introductionmentioning

confidence: 99%

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Testing the tools for revealing and characterizing the iodine–iodine halogen bond in crystals

Барташевич

Yushina

Kropotina

et al. 2017

Acta Crystallogr B Struct Sci Cryst Eng Mater

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To understand what tools are really suitable to identify and classify the iodine-iodine non-covalent interactions in solid organic polyiodides, we have examined the anisotropy of the electron density within the iodine atomic basin along and across the iodine-iodine halogen bond using the Laplacian of electron density, one-electron potential and electron localization function produced by Kohn-Sham calculations with periodic boundary conditions. The Laplacian of electron density exhibits the smallest anisotropy and yields a vague picture of the outermost electronic shells. The one-electron potential does not show such a deficiency and reveals that the valence electron shell for the halogen-bond acceptor iodine is always wider than that for the halogen-bond donor iodine along its σ-hole direction. We have concluded that the one-electron potential is the most suitable for classification of the iodine-iodine bonds and interactions in complicated cases, while the electron localization function allows to distinguish the diiodine molecule bonded with the monoiodide anion from the typical triiodide anion.

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Section: Calculationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Testing the tools for revealing and characterizing the iodine–iodine halogen bond in crystals

Барташевич

Yushina

Kropotina

et al. 2017

Acta Crystallogr B Struct Sci Cryst Eng Mater

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“…While these functional groups participate in intermolecular close-contacts the coordination environment of the interhalogen or dihalogen remains unaffected. 26 Spectroscopic probes of the structure and reactivity of interhalogen species remain a vibrant area of study. Previously the only reported complex of H 2 with a dihalogen or interhalogen species was H 2 Á Á ÁI 2 .…”

Section: Interhalogens and Polyhalidesmentioning

confidence: 99%

Halogens and noble gases

Justik

2008

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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This chapter reviews the literature reported during 2007 concerning the elemental halogens and noble gases as well as compounds containing these elements in their positive oxidation states. HighlightsThe 2007 literature for halogen chemistry is highlighted by the first accurate ab initio diatomic dissociation curve for F 2 , the preparation of a new metal iodate for nonlinear optics applications and the crystal structure of a novel hypervalent iodinecontaining polymer having 12-atom hexagonal rings. Noble gas chemistry advances include the first reproducible preparation of XeOF 2 and the first solid-state 131 Xe NMR study of a xenon-containing compound.

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Formation of T‐Shaped versus Charge‐Transfer Molecular Adducts in the Reactions Between Bis(thiocarbonyl) Donors and Br₂ and I₂

Mancini

Aragoni

Bricklebank

et al. 2012

Chemistry An Asian Journal

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The reactions of 4,5,6,7-tetrathiocino-[1,2-b:3,4-b']-1,3,8,10-tetrasubstituted-diimidazolyl-2,9-dithiones (R(2),R'(2)-todit; 1: R=R'=Et; 2: R=R'=Ph; 3: R=Et, R'=Ph) with Br(2) exclusively afforded 1:1 and 1:2 "T-shaped" adducts, as established by FT-Raman spectroscopy and single-crystal X-ray diffraction in the case of complex 1·2Br(2). On the other hand, the reactions of compounds 1-3 with molecular I(2) provided charge-transfer (CT) "spoke" adducts, among which the solvated species 3·2I(2)·(1-x)I(2)·xCH(2)Cl(2) (x=0.94) and (3)(2)·7I(2)·xCH(2)Cl(2), (x=0.66) were structurally characterized. The nature of all of the reaction products was elucidated based on elemental analysis and FT-Raman spectroscopy and supported by theoretical calculations at the DFT level.

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The role of functional nitro and cyano groups in the self‐assembly of 1,3‐dithiole‐2‐thione–halogen adducts

Cited by 6 publications

References 19 publications

Testing the tools for revealing and characterizing the iodine–iodine halogen bond in crystals

Testing the tools for revealing and characterizing the iodine–iodine halogen bond in crystals

Halogens and noble gases

Formation of T‐Shaped versus Charge‐Transfer Molecular Adducts in the Reactions Between Bis(thiocarbonyl) Donors and Br₂ and I₂

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The role of functional nitro and cyano groups in the self‐assembly of 1,3‐dithiole‐2‐thione–halogen adducts

Cited by 6 publications

References 19 publications

Testing the tools for revealing and characterizing the iodine–iodine halogen bond in crystals

Testing the tools for revealing and characterizing the iodine–iodine halogen bond in crystals

Halogens and noble gases

Formation of T‐Shaped versus Charge‐Transfer Molecular Adducts in the Reactions Between Bis(thiocarbonyl) Donors and Br2 and I2

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Formation of T‐Shaped versus Charge‐Transfer Molecular Adducts in the Reactions Between Bis(thiocarbonyl) Donors and Br₂ and I₂