Chalcogen–chalcogen interactions in trichalcogenaferrocenophanes. Crystal structure of 2-selena-1,3-ditellura[3]ferrocenophane [Fe(C5H4Te)2Se]

Karjalainen, Minna M.; Oilunkaniemi, Raija; Laitinen, Risto S.

doi:10.1016/j.ica.2012.03.054

Cited by 12 publications

(10 citation statements)

References 14 publications

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“…Among the chalcogen–chalcogen interactions, the S···S contact has garnered immense attention due to their wide applications such as in organic conductors, and nanotube formation . S···S interactions have also been observed to play a very important role in the processes of molecular self-assembly. ,− One of the earliest studies on S···S contacts revealed that there is a preferred orientation of electrophilic and nucleophilic regions in divalent sulfur atoms . In another study, a CSD analysis and a theoretical investigation discussed the stabilizing characteristics of S···S contact .…”

Section: Introductionmentioning

confidence: 99%

Crystallographic and Theoretical Investigation on the Nature and Characteristics of Type I C═S···S═C Interactions

Shukla

Chopra

2016

Crystal Growth & Design

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Depending on the electronic environment, chalcogen atoms (mainly S, Se, Te) can act as both acceptor and donor during the formation of a noncovalent interaction. This dual behavior of chalcogens can lead to the formation of highly stabilized chalcogen-chalcogen interactions [1]. Among the chalcogen-chalcogen interactions, S…S interactions has garnered immense attention due to several applications such as in organic conductors and nanotube formations. Role of S…S interactions in molecular structures has been explored both experimentally and computationally [2]. However, a closer look at the literature reveals that most studies on S…S is centered around sp3 hybridized sulfur atom with a negligible focus to sp2 hybridized sulfur atom. A simple Cambridge Structural Database [2] search revealed that there are more than 1000 structures having sp2 hybridized organic sulfur participating in the formation of C=S…S=C interactions. However, a systematic and detailed investigation of this interaction in crystal structures has not be explored previously. In this study, we have analyzed the nature and characteristics of C═S···S═C chalcogen-chalcogen interactions by screening the Cambridge Structural Database. In addition to this, we have also performed a topological analysis and binding energy calculations on full scale dimers extracted from the Cambridge Structure Database in addition to analysing C═S···S═C interactions in (X2CS)2 model systems where X = −H, −NH2, −OH, −F, −Cl by means of the electrostatic potential maps and energy decomposition analysis [1] Bleiholder, C. et al. (2006).

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Section: Introductionmentioning

confidence: 99%

Crystallographic and Theoretical Investigation on the Nature and Characteristics of Type I C═S···S═C Interactions

Shukla

Chopra

2016

Crystal Growth & Design

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“…(9) were prepared according to the literature procedures. 11,13,14,18,19 The 77 Se and 125 Te NMR spectra of 2-9 were recorded from the crude products in THF, as appropriate. After purification using column chromatography involving silica gel as a stationary phase and a mixture of hexane and dichloromethane as an eluant, red X-ray quality crystals of 3, 6, and 7 were obtained from the hexane/CH 2 Cl 2 mixture.…”

Section: Introductionmentioning

confidence: 99%

Chalcogen–chalcogen secondary bonding interactions in trichalcogenaferrocenophanes

et al. 2016

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The solid-state structures of all members in the series of trichalcogenaferrocenophanes [FeĲC 5 H 4 E) 2 E′] (E, E′ = S, Se, Te) (1-9) have been explored to understand the trends in secondary bonding interactions (SBIs) between chalcogen elements sulfur, selenium, and tellurium. To complete the series, the crystal structures of the four hitherto unknown complexes [Fe(C 5 H 4 S) 2 Te] (3), [Fe(C 5 H 4 Se) 2 S] (4), [Fe(C 5 H 4 Se) 2 Te] (6), and [Fe(C 5 H 4 Te) 2 S] (7) have been determined in this contribution. The packings of all complexes 1-9 were considered by DFT calculations at the PBE0/pob-TZVP level of theory using periodic boundary conditions. The intermolecular close contacts were considered by QTAIM and NBO analyses. The isomorphous complexes [Fe(C 5 H 4 S) 2 S] (1), [Fe(C 5 H 4 S) 2 Se] (2), and [Fe(C 5 H 4 Se) 2 Se] (5a) form dimers via weak interactions between the central chalcogen atoms of the two trichalcogena chains of adjacent complexes. In the second isomorphous series consisting of [Fe(C 5 H 4 Se) 2 S] (4) and 5b, the complexes are linked together into continuous chains by short contacts via the terminal selenium atoms. The intermolecular chalcogen-chalcogen interactions are significantly stronger in complexes [Fe(C 5 H 4 S) 2 Te] (3), [Fe(C 5 H 4 Se) 2 Te] (6), and [Fe(C 5 H 4 Te) 2 E′] (E′ = S, Se, Te) (7-9), which contain tellurium. The NBO comparison of donor-acceptor interactions in the lattices of [Fe(C 5 H 4 S) 2 S] (1), [Fe(C 5 H 4 Se) 2 Se] (5a and 5b), and [Fe(C 5 H 4 Te) 2 Te] (9) indeed shows that the n(5p Te) 2 → σ*(Te-Te) interactions in 9 are the strongest. All other interaction energies are significantly smaller even in the case of tellurium. The computed natural charges of the chalcogen atoms indicate that electrostatic effects strengthen the attractive interactions in the case of all chalcogen atoms.

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“…Te contacts. 12,13 Such structural peculiarities have been interpreted as indicators for secondary bonding interactions, 14,15 but even without closed shell interaction, the proximity of intermolecular Se-chains may affect the tendency for interaction or charge separation upon irradiation related to those occurring in the Xerox process.…”

Section: Resultsmentioning

confidence: 99%

“…H and13 C NMR spectra have been recorded with a Bruker AMX 360 spectrometer (Bruker Biospin Gmbh; Rheinstetten, Germany) operating at 360 MHz ( 1 H) and 91 MHz ( 13 C) and with a Varian Unity 400 spectrometer (Varian, Inc., Palo Alto, USA) operating at 400 MHz ( 1 H) and 101 MHz ( 13 C). Residual solvent signals have been used as internal reference for 1 H and 13 C spectra.…”

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confidence: 99%

A Structural Comparison of Organoterminated Selenide, Diselenide, and Triselenide

Kahr

Moser

Spirk

et al. 2014

Phosphorus, Sulfur, and Silicon and the Related Elements

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Chalcogen–chalcogen interactions in trichalcogenaferrocenophanes. Crystal structure of 2-selena-1,3-ditellura[3]ferrocenophane [Fe(C5H4Te)2Se]

Cited by 12 publications

References 14 publications

Crystallographic and Theoretical Investigation on the Nature and Characteristics of Type I C═S···S═C Interactions

Crystallographic and Theoretical Investigation on the Nature and Characteristics of Type I C═S···S═C Interactions

Chalcogen–chalcogen secondary bonding interactions in trichalcogenaferrocenophanes

A Structural Comparison of Organoterminated Selenide, Diselenide, and Triselenide

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