Iodoperchlorobenzene acts as a dual halogen-bond donor to template a [2 + 2] cycloaddition reaction within an organic co-crystal

Shapiro, Nicole M.; Bosch, Eric; Unruh, Daniel K.; Krueger, Herman; Groeneman, Ryan H.

doi:10.1039/d1ce01194d

Cited by 8 publications

(3 citation statements)

References 32 publications

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“…After 30 h of irradiation, integration of the two peaks indicated an overall yield of 96% for the [2 + 2] cycloaddition reaction for each polymorph containing solid. It is noteworthy that a similar yield was observed for a cocrystal containing iodoperchlorobenzene with BPE …”

Section: Introductionsupporting

confidence: 72%

“…It is noteworthy that a similar yield was observed for a cocrystal containing iodoperchlorobenzene with BPE. 19 To gain insight into the binding energies within these two polymorphs a Density Functional Theory (DFT) calculation was performed using the Gaussian 16 package. In particular, the M06-2X functional was used along with the aug-cc-pVTZ basis set for all DFT calculations.…”

Section: ■ Introductionmentioning

confidence: 99%

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Photoreactive Polymorphic Cocrystals Utilizing a Molecular Template with Dual Halogen and Hydrogen Bonding Capabilities

Bosch

Powell

Krueger

et al. 2023

Crystal Growth & Design

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The ability of 1,2,4,5-tetrachloro-3-iodobenzene to act as a template to form a pair of polymorphic cocrystals with trans-1,2-bis(4-pyridyl)ethylene is reported. After exposure to ultraviolet light, a nearly quantitative yield for the [2 + 2] cycloaddition reaction was observed for both concomitant cocrystals. These crystalline solids engage in both I•••N halogen bonds along with nontraditional C−H•••N hydrogen bond which results in a one-dimensional chain. In addition, the components homogeneous π−π stack which positions the carbon−carbon double bond on the reactant molecule in a suitable orientation to undergo a photoinduced cyclization reaction.

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Section: Introductionsupporting

confidence: 72%

Section: ■ Introductionmentioning

confidence: 99%

Photoreactive Polymorphic Cocrystals Utilizing a Molecular Template with Dual Halogen and Hydrogen Bonding Capabilities

Bosch

Powell

Krueger

et al. 2023

Crystal Growth & Design

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“…Recently, we have also reported on the ability of iodoperchlorobenzene to act as a dual halogen-bond donor by engaging in both I⋯N and Cl⋯N halogen bonds within a series of isostructural solids. 9 In these co-crystals, both the traditional and stronger I⋯N halogen bond along with the cooperative and weaker Cl⋯N halogen bond are required to form these linear polymeric chains. The ability of the Cl-atom to form this secondary halogen bond is in contrast with the role of the electron rich F-atom that can act as a hydrogen-bond acceptor.…”

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confidence: 99%

Cooperative non-covalent interactions and synthetic feed as driving forces to structural diversity within organic co-crystals containing isosteric perhalobenzenes

et al. 2022

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Structurally Innovative Benzimidazole‐fused Ionic Organoselenium Compounds: Prevalence of Se⋅⋅⋅N/Se Chalcogen Bonds with the Selenocyanate Receptor

Banerjee,

Sufian,

Bhabak

2024

Eur J Org Chem

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The non‐covalent interactions in molecules play important roles towards their applications in various aspects such as molecular recognition, catalysis, supramolecular chemistry, structural biology, pharmacology etc. Interestingly, among various non‐bonding interactions, chalcogen bonding (ChB) has been extensively studied in different facets of crystal engineering over the last several years. The present study demonstrates the presence of Se···N or Se···Se ChB in the benzimidazole‐fused cyclic selenazonium selenocyanates (6‐8), cyclic selenazinium selenocyanates (9‐10) and the acyclic benzimidazolium analogs having two different types of selenocyanate units (11‐12). The final organoselenium compounds were synthesized from benzimidazole in several steps in reasonably good yields. The single crystal X‐ray structures of the compounds revealed that both the N atom and Se atom of the negatively charged SeCN unit act as ChB acceptors in building the Se···N or Se···Se ChB interactions along with the additional hydrogen bonding (HB) interactions. Moreover, the structural optimization and natural bond orbital (NBO) analyses were carried out using density functional theory (DFT) to calculate the natural charges on different Se centers and the strength of second‐order perturbation energy (E2) for the ChB interactions. Finally, electrostatic potential surface (SEP) of the compounds was developed to visualize the formation of σ‐holes.

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Iodoperchlorobenzene acts as a dual halogen-bond donor to template a [2 + 2] cycloaddition reaction within an organic co-crystal

Abstract: The formation of three isostructural co-crystals that utilize iodoperchlorobenzene as a dual halogen-bond donor is reported.

Cited by 8 publications

References 32 publications

Photoreactive Polymorphic Cocrystals Utilizing a Molecular Template with Dual Halogen and Hydrogen Bonding Capabilities

Photoreactive Polymorphic Cocrystals Utilizing a Molecular Template with Dual Halogen and Hydrogen Bonding Capabilities

Cooperative non-covalent interactions and synthetic feed as driving forces to structural diversity within organic co-crystals containing isosteric perhalobenzenes

Structurally Innovative Benzimidazole‐fused Ionic Organoselenium Compounds: Prevalence of Se⋅⋅⋅N/Se Chalcogen Bonds with the Selenocyanate Receptor

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