Crystal Structures of Chloro and Bromo Cyanoacetylene.

Bjorvatten, T.; Rasmussen, Svend Erik; Seip, H. M.; Gronowitz, Salo; Christiansen, Harald; Rosén, Ulf

doi:10.3891/acta.chem.scand.22-0410

Cited by 26 publications

(23 citation statements)

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“…1-Iodoalkynes 197 , 398 , 399 , 567 − 569 have been used much more frequently ( Figure 56 ) than brominated analogues, 209 , 570 , 571 and to the best of our knowledge, the structures of only two halogen-bonded 1-chloroalkynes are reported. 192 , 572 The remarkable ability of 1-iodoalkynes to work as XB donors, control the structure of solid architectures, and switch on or tune functional properties has been exploited in the obtainment of supramolecular liquid crystals 573 and organic conductors and magnets. 574 − 576 …”

Section: Nature Of the Halogen Bondmentioning

confidence: 99%

The Halogen Bond

et al. 2016

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The halogen bond occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a halogen atom in a molecular entity and a nucleophilic region in another, or the same, molecular entity. In this fairly extensive review, after a brief history of the interaction, we will provide the reader with a snapshot of where the research on the halogen bond is now, and, perhaps, where it is going. The specific advantages brought up by a design based on the use of the halogen bond will be demonstrated in quite different fields spanning from material sciences to biomolecular recognition and drug design.

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Section: Nature Of the Halogen Bondmentioning

confidence: 99%

The Halogen Bond

et al. 2016

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“…Short intermolecular N... X distances are well known in the cyanogen halides (C1CN, Heiart & Carpenter, 1956;BrCN, Geller & Schawlow, 1955;ICN, Ketelaar & Zwartsenberg, 1939) and have recently been found in the halocyanoacetylenes (CICCCN and BrCCCN, Bjorvatten, 1968;ICCCN, Borgen, Hassel & Romming, 1962). These short distances have been interpreted as indicating donor-acceptor or acid-base interactions between adjacent molecules.…”

Section: Introductionmentioning

confidence: 95%

The crystal structures of 2,4,6-trichlorobenzonitrile and 2,4,6-tribromobenzonitrile

Carter¹,

Britton²

1972

Acta Crystallogr Sect B

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2,4,6-Trichlorobenzonitrile crystallizes in the monoclinic space group P21/e with a = 3"97 (1), b = 16.06 (3), c= 12.84 (2) A, and fl= 91"0 (3) °. 2,4,6-Tribromobenzonitrile crystallizes in the monoclinic space group P21/m with a = 8.82 (2), b = 10.34 (2), c= 4-89 (1)/~, and fl= 95.8 (2) °. The structures of both compounds were determined from three-dimensional film data and were refined to conventional R values of 0"134 and 0-089, respectively. Neither molecular structure contains any unusual features. The packing of the molecules in the crystals is dominated by weak Lewis acid-base interactions, CN...X, between the cyanide groups and ortho halogen atoms in a manner reminiscent of the dimerization of carboxylic acids. In the chloro compound these interactions lead to dimers, with CN..-CI distances of 3.22 A. In the bromo compound these interactions lead to infinite chain-like polymers, with CN. • • Br distances of 3.06/~.

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“…The halogen bond is an especially directional interaction, more so than the hydrogen bond, due to the localization of the σ‐hole exactly along the elongation of the covalent bond of which the halogen atom is a part [16–18] . The strength of the halogen bond is also easily tunable by varying both the halogen atom involved, with donor ability changing in the order I > Br > Cl > F, as well as modifying electron‐withdrawing ability of the moieties bound to the halogen atom [19–21] . Additionally, the typical halogen bond donor site is significantly less hydrophilic than a typical hydrogen bond donor site.…”

Section: Introductionmentioning

confidence: 99%

Halogen Bonding in Dithiane/Iodofluorobenzene Mixtures: A New Class of Hydrophobic Deep Eutectic Solvents

et al. 2021

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While research into deep eutectic solvents (DESs) has expanded over the previous two decades, the focus has remained on the utilization of hydrogen bond donors in these systems. Additionally, the majority of the known DESs rely on at least one ionic component. Through the combination of 1,3‐dithiane and 1,2‐diiodo‐3,4,5,6‐tetrafluorobenzene (1,2‐F4DIB), we report the first known DES based on halogen bonding. This mixture remains a liquid, with a eutectic melting temperature of 13.7 °C over a range of 1,3‐dithiane mole fraction (0.35 to 0.75). Additionally, cocrystals of 1,3‐ and 1,4‐dithiane with 1,2‐, 1,3‐, and 1,4‐F4DIB, as well as 1,3,5‐trifluoro‐2,4,6‐triiodobenzene were studied via single‐crystal X‐ray diffraction. These data reveal a wide range of halogen bonding strengths (0.85

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Crystal Structures of Chloro and Bromo Cyanoacetylene.

Cited by 26 publications

References 0 publications

The Halogen Bond

The Halogen Bond

The crystal structures of 2,4,6-trichlorobenzonitrile and 2,4,6-tribromobenzonitrile

Halogen Bonding in Dithiane/Iodofluorobenzene Mixtures: A New Class of Hydrophobic Deep Eutectic Solvents

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