The role of charge assisted arylhalogen–halide ion interactions in the structures of the dibromopyridinium halide salts

Awwadi, Firas F.; Willett, Roger D.; Twamley, Brendan

doi:10.1016/j.molstruc.2008.07.028

Cited by 26 publications

(31 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Other imidazolium‐based structures were also found to form halogen bonds, which will be covered in more detail in the section on halogen bonding in solution. The structure of 2,5‐dibromopyridinium chloride was reported recently, exhibiting a Br ··· Cl – XB with a length of 3.12 Å (13 % reduction, MOPHOP) 35b…”

Section: Halogen Bonding With Organic Molecules In the Solid Statementioning

confidence: 90%

Alternative Motifs for Halogen Bonding

et al. 2013

View full text Add to dashboard Cite

The halogen‐bonding interaction is one of the rising stars in supramolecular chemistry. Although other weak interactions and their influence on the structure and chemistry of various molecules, complexes and materials have been investigated thoroughly, the field of halogen bonding is still quite unexplored and its impact on chemistry in general is yet to be fully revealed. In principle, every Y–X bond (Y = electron‐withdrawing atom or moiety, X = halogen atom) can act as a halogen‐bond donor when the halogen is polarized enough by Y. Perfluorohalocarbons are iconic halogen‐bond donor molecules in which Y is a perfluorinated aryl or alkyl moiety and X is either iodine or bromine. In this article, alternative halogen‐bond motifs such as X2···A and Ar–X···A [A = Lewis basic halogen‐bond‐accepting atom of a molecule or ion; Ar = neutral or charged (hetero)aromatic system] are reviewed. In addition, haloalkenes, haloalkynes, N‐haloamides and other non‐metallic halogen‐bond donors and their respective halogen‐bonded structures will also be described. Although purely organic halogen‐bonding motifs are very prominent, the role of metal complexes in halogen bonding is becoming increasingly evident as well, which is also reflected in this review. Finally, halogen bonding in solution is briefly highlighted. Contemporary research is proving that halogen bonding is more than a solid‐state phenomenon and is now a well‐recognized weak interaction in chemistry.

show abstract

Section: Halogen Bonding With Organic Molecules In the Solid Statementioning

confidence: 90%

Alternative Motifs for Halogen Bonding

et al. 2013

View full text Add to dashboard Cite

show abstract

“…159 The type II interaction has been described as the true form of XB as it arises from an attractive nucleophile−electrophile pairing of the electropositive σ-hole of one polarized halogen with the electronegative equatorial belt of another polarized halogen, whereas the type I interaction is geometrically based since it arises from close packing and is observed for all halogens. 153 Indeed, fluorine has been shown to participate in type II interactions despite the more prevalent, close-packed type I interaction, and in one case the type II interaction has been studied in depth using experimental charge density analysis. 160 Analysis of the crystal structure of pentafluorophenyl-2,2′-bisthiazole revealed short type II F···F interactions, stabilized by a surrogate C−F···S interaction ( Figure 15).…”

Section: Fundamentalsmentioning

confidence: 99%

Halogen Bonding in Supramolecular Chemistry

et al. 2015

View full text Add to dashboard Cite

CONTENTS 1. Introduction to Halogen Bonding 7119 1.1. Nature of the Halogen Bond 7119 1.2. Scope of the Review 7120 2. Computational and Theoretical Investigations of Halogen Bonding 7120 2.1.Quantum Mechanics Methods 7120 2.2. σ-Hole Model of Halogen Bonding 7120 2.3. Other Contributions to the Nature of Halogen Bonding 7122 2.4. Recent Examples of Computationally Investigated Halogen-Bonded Complexes 7123 2.4.1. XB to Neutral Species 7123 2.4.2. XB to Anions 7126 2.4.3. XB in Protein−Ligand Complexes 7127 2.4.4. Electron-Transfer Processes Affected by XB Interactions 7127 2.5. Classical Force Field Calculations 7127 2.6. Conclusions and Outlook 7129 3. Gas-Phase Studies of Halogen-Bonding Interactions 7130 4. Halogen Bonding in the Solid State 7131 4.1. Introduction to Crystal Engineering and Functional Materials 7131 4.2. Fundamentals 7132 4.3. Halogen-Bonding Hierarchy 7134 4.3.1. Ranking Halogen-Bond Donors 7134 4.3.2. HB/XB Complementarity/Competition 7136 4.3.3. Predicting XBs 7138 4.4. Control of Solid-State Supramolecular Architectures 7138 4.4.1. Polymorphism 7138 4.4.2. Stoichiometry 7139 4.4.3. Tautomeric Control 7140 4.4.4. XBs Involving Metals and Metal-Bound XBs 7140 4.4.5. XB with Anions in the Solid State 4.5. Solid-State Architectures 4.6.

show abstract

“…2-IEP•HI was not obtained when repeating the synthesis with HI gas;i nstead, 2-IEP•HI 3 was obtained, perhaps due to the decompositiono fH Ig as into I 2 .T he structure of 2-IEP•HI 3 consists of an open framework, as shown in Figure 2 These charged dimers bear some resemblance to previously reported structures based on 3-bromopyridine. [56][57][58][59] Further,t he ribbon motif reported for the 2-IEP•HCl and 2-IEP•HBr structuresi sa lso presenti nt he 3-IEP•HBr and 3-IEP•HI structures. In these cases, the halides in the charged dimers are coordinated by the atoms in the ortho-and metapositions relative to the NÀH + moiety.…”

Section: Introductionmentioning

confidence: 99%

Comparing the Halogen Bond to the Hydrogen Bond by Solid‐State NMR Spectroscopy: Anion Coordinated Dimers from 2‐ and 3‐Iodoethynylpyridine Salts

Szell

Cavallo

Terraneo

et al. 2018

Chemistry A European J

View full text Add to dashboard Cite

Halogen bonding is an increasingly important tool in crystal engineering, and measuring its influence on the local chemical and electronic environment is necessary to fully understand this interaction. Here, we present a systematic crystallographic and solid-state NMR study of self-complementary halogen-bonded frameworks built from the halide salts (HCl, HBr, HI, HI ) of 2-iodoethynylpyridine and 3-iodoethynylpyridine. A series of single crystal X-ray structures reveals the formation of discrete charged dimers in the solid state, directed by simultaneous X ⋅⋅⋅H-N hydrogen bonds and C-I⋅⋅⋅X halogen bonds (X=Cl, Br, I). Each compound was studied using multinuclear solid-state magnetic resonance spectroscopy, observing H to investigate the hydrogen bonds and C, Cl, and Br to investigate the halogen bonds. A natural localized molecular orbital analysis was employed to help interpret the experimental results. H SSNMR spectroscopy reveals a decrease in the chemical shift of the proton participating in the hydrogen bond as the halogen increases in size, whereas the C SSNMR reveals an increased C chemical shift of the C-I carbon for C-I⋅⋅⋅X relative to C-I⋅⋅⋅N halogen bonds. Additionally, Cl and Br SSNMR, along with computational results, have allowed us to compare the C-I⋅⋅⋅X halogen bond involving each halide in terms of NMR observables. Due to the isostructural nature of these compounds, they are ideal cases for experimentally assessing the impact of different halogen bond acceptors on the solid-state NMR response.

show abstract

The role of charge assisted arylhalogen–halide ion interactions in the structures of the dibromopyridinium halide salts

Cited by 26 publications

References 41 publications

Alternative Motifs for Halogen Bonding

Alternative Motifs for Halogen Bonding

Halogen Bonding in Supramolecular Chemistry

Comparing the Halogen Bond to the Hydrogen Bond by Solid‐State NMR Spectroscopy: Anion Coordinated Dimers from 2‐ and 3‐Iodoethynylpyridine Salts

Contact Info

Product

Resources

About