Intramolecular S⋯S and S⋯O close contacts in 1,8-bis(phenylsulfanyl)naphthalene derivatives of different sulfur valence state: an X-ray study

Nagy, Péter; Szabó, Dénes; Kapovits, I.; Kucsman, Árpád; Argay, Gyula; Kàlmán, Alajos

doi:10.1016/s0022-2860(01)00821-3

Cited by 33 publications

(130 citation statements)

References 29 publications

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“…56,57,58 The structural geometry of compounds 1-15 can be described by the orientation of the naphthyl and phenyl rings relative to the C(ar)-G(1)-C(ar) and the C(ar)-Z(2)-CI planes, calculated from torsion angles θ and γ respectively (see Table 7, Figure 1). 64 When θ and γ approach 90° the orientation is categorized as axial whilst an equatorial conformation is denoted by angles close to 180°. 64 Conformations in between axial and equatorial are classified as twist.…”

Section: Resultsmentioning

confidence: 99%

“…64 Conformations in between axial and equatorial are classified as twist. 64 For angle θ, axial conformations correspond to the "type A" structure presented by Nakanishi et al (G-C Ph /Z-C Ph bond lies perpendicular to the naphthyl plane). 65 An equatorial conformation for θ aligns the G-C Ph /Z-C Ph bond on or close to the plane ("type B") 65 and a twist conformation relates to Nakanishi"s "type C" (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

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Hypervalent Adducts of Chalcogen-Containing peri-Substituted Naphthalenes; Reactions of Sulfur, Selenium, and Tellurium with Dihalogens

et al. 2010

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X-E···E` 3c-4e type interaction. Upon treatment with diiodine D2 and D3 form "Z-shaped" "extended spoke" adducts containing an uncommon 2:3 donor/chalcogen ratio and incorporating chains of I 2 held together by rare I···I interactions. As expected, "see-saw" 10-E-4 adducts are formed following the reaction of Te-donors D4-D7 {Nap [TePh][X] (X = Br, I); Nap [TePh][EPh] (E = Se, S)} with the dihalogens. Naphthalene distortion in general is comparable between respective donor compounds and products 1-15. Ionic species 2 and 3 display a noticeable reduction in molecular distortion explained by the relief of steric strain via weak peri-interactions and the onset of 3c-4e bonding.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Hypervalent Adducts of Chalcogen-Containing peri-Substituted Naphthalenes; Reactions of Sulfur, Selenium, and Tellurium with Dihalogens

et al. 2010

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“…When the axis of the chalcogen p-orbitals aligns along the mean aromatic plane (A or AA type conformations, see below for definitions) repulsion is relatively high. 6,27,29 Conversely, a parallel alignment of the chalcogen porbitals to the mean plane (B or AB type conformations) reduces the repulsive interactions and notably shorter peri-separations with respect to the size of the atoms are observed. 6,27,29 Additionally, the B/AB type configuration affords a quasi-linear three-body fragment across the peri-gap, which appears to promote the formation of an attractive three-center, four electron type interaction.…”

Section: Introductionmentioning

confidence: 99%

“…6,27,29 Conversely, a parallel alignment of the chalcogen porbitals to the mean plane (B or AB type conformations) reduces the repulsive interactions and notably shorter peri-separations with respect to the size of the atoms are observed. 6,27,29 Additionally, the B/AB type configuration affords a quasi-linear three-body fragment across the peri-gap, which appears to promote the formation of an attractive three-center, four electron type interaction. 27 Evidence supporting a weak non-covalent peri-interaction in AB type compounds Nap(TePh)(SePh) N4 and Acenap(TePh)(SePh) A13 (Figure 1) is observed in their respective 125 Te NMR spectra.…”

Section: Introductionmentioning

confidence: 99%

“…The absolute configuration of the aromatic ring systems and methyl functionality in 2-13 can be classified by the relative alignment of the naphthalene and acenaphthene backbones and the aryl moieties with respect to the C(ar)-E-C(ar) planes. 6,23,25,27,29 This is calculated from torsion angles θ and γ [ Table 2; Figure 2] which define the rotation of the aryl groups around the E-C Nap/Acenap bonds and E-C Ph bonds, respectively. When θ approaches 90°, the orientation is denoted axial; the respective E-C Ar bond aligns perpendicular to the mean least-squares plane and corresponds to a type A structure.…”

Section: Introductionmentioning

confidence: 99%

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Noncovalent Interactions in Peri-Substituted Chalconium Acenaphthene and Naphthalene Salts: A Combined Experimental, Crystallographic, Computational, and Solid-State NMR Study

et al. 2012

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ABSTRACT:Twelve related monocation chalconium salts [{Nap(EPh)(E`Ph)Me} + {CF 3 SO 3 } -] 2-4, [{Acenap(Br)(EPh)Me}{CF 3 SO 3 } -] 5-7 and [{Acenap(EPh)(E`Ph)Me} + {CF 3 SO 3 } -] 8-13, have been prepared and structurally characterized. For their synthesis naphthalene compounds [Nap(EPh)(E`Ph)] (Nap = naphthalene-1,8-diyl; E/E` = S, Se, Te) N2-N4 and associated acenaphthene derivatives [Acenap(EPh)(E`Ph)] (Acenap = acenaphthene-5,6-diyl; E/E` = S, Se, Te) A5-A13 were independently treated with a single molar equivalent of methyl trifluoromethanesulfonate [MeOTf]. In addition, reaction of bistellurium compound A10 with two equivalents of MeOTf afforded the doubly methylated dication salt [{Acenap(TePhMe) 2 } 2+ {(CF 3 SO 3 ) 2 } 2-}] 14. Distortion of the rigid naphthalene and acenaphthene backbone away from the ideal was investigated in each case and correlated in general with the steric bulk of the interacting atoms located at the proximal peripositions. Naturally, introduction of the ethane linker in acenaphthene compounds increased the splay of the bay region compared with equivalent naphthalene derivatives resulting in greater peri-distances. The conformation of the aromatic rings and subsequent location of p-type lone-pairs has a significant impact on the geometry of the peri-region, with anomalies in periseparations correlated to the ability of the frontier orbitals to take part in attractive or repulsive interactions. In all but one of the monocations a quasi-linear three-body C Me -E···Z (E = Te, Se, S; Z = Br/E) fragment provides an attractive component for the E···Z interaction. Density-functional studies have confirmed these interactions and suggested the onset of formation of threecenter, four-electron bonding under appropriate geometric conditions, becoming more prevalent as heavier congeners are introduced along the series. The increasingly large J values for Se-Se, Te-Se and Te-Te coupling observed in the 77 Se and 125 Te NMR spectra for 1, 3, 4, 9, 10 and 13 give further evidence for the existence of a weakly-attractive through-space interaction. INTRODUCTIONUnderstanding the nature of atomic interactions and the strength of chemical bonds is an integral feature underpinning all aspects of chemistry, biology and materials science and as such has always attracted great attention. Pioneering work on the electronic theory of the covalent bond led to a greater understanding of strong bonding (covalent/ionic), 1 but ambiguity over the role of weak inter-and intra-molecular non-covalent interactions continues to intrigue chemists. 2-4 Designing structural architectures which invoke novel and unusual bonding interactions is indispensable for developing the theory of nonbonded forces and the chemical bond and is therefore an intriguing field of study. 5,6 Non-covalent interactions can be attractive or repulsive in nature and are continually being highlighted within a diverse

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Recent Advances of Structural Chemistry of Organoselenium and Organotellurium Compounds

Nakanishi

Hayashi

Hashimoto

et al. 2014

Patai's Chemistry of Functional Groups

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The recent advances of structural chemistry of organoselenium and organotellurium compounds are reviewed. The basic concepts of structural chemistry of the compounds are well summarized in Chapter 3 of Volume 1 in this series. About 9,000 structures for the compounds have been reported since then, therefore only selected results can be discussed here. Such compounds are expected to contain at least one CE (E = Se or Te) bond, although those with no CE bonds are also discussed, as necessary. Compounds containing CE (E = Se and Te) are discussed in some detail. Structures of unstable and/or reactive species are explained in detail, which are stabilized by the formation of dimers or higher oligomers or using large protecting groups. Bis‐selenides and bis‐tellurides and the derivatives at the naphthalene 1,8‐positions and the related systems are discussed in detail. The compounds containing hypervalent interactions are also discussed in detail. The idea is applied to the intramolecular and intermolecular linear interactions in crystals. In this connection, the extended hypervalent interactions are also explained in detail for the linear interactions longer than three, exemplified by typical cases and unique cases in crystals.

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Intramolecular S⋯S and S⋯O close contacts in 1,8-bis(phenylsulfanyl)naphthalene derivatives of different sulfur valence state: an X-ray study

Cited by 33 publications

References 29 publications

Hypervalent Adducts of Chalcogen-Containing peri-Substituted Naphthalenes; Reactions of Sulfur, Selenium, and Tellurium with Dihalogens

Hypervalent Adducts of Chalcogen-Containing peri-Substituted Naphthalenes; Reactions of Sulfur, Selenium, and Tellurium with Dihalogens

Noncovalent Interactions in Peri-Substituted Chalconium Acenaphthene and Naphthalene Salts: A Combined Experimental, Crystallographic, Computational, and Solid-State NMR Study

Recent Advances of Structural Chemistry of Organoselenium and Organotellurium Compounds

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