On the Importance of Pnictogen and Chalcogen Bonding Interactions in Supramolecular Catalysis

Frontera, Antonio; Bauzá, Antonio

doi:10.3390/ijms222212550

Cited by 50 publications

(52 citation statements)

References 126 publications

(170 reference statements)

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“…Noncovalent interactions show up in different flavors, including, for example, hydrogen bonding [ 23 ], halogen bonding [ 24 ], tetrel bonding [ 25 , 26 , 27 ], chalcogen bonding [ 28 ], pnictogen bonding [ 29 , 30 , 31 , 32 ], aerogen bonding [ 33 ], van der Waals interactions [ 34 ], and several others [ 35 ]. They are the result of attractive engagements between sites of unequal charge density and are often identified to be of Coulombic origin (a positive site attracting a negative one).…”

Section: Introductionmentioning

confidence: 99%

The Phosphorus Bond, or the Phosphorus-Centered Pnictogen Bond: The Covalently Bound Phosphorus Atom in Molecular Entities and Crystals as a Pnictogen Bond Donor

2022

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The phosphorus bond in chemical systems, which is an inter- or intramolecular noncovalent interaction, occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a covalently or coordinately bonded phosphorus atom in a molecular entity and a nucleophile in another, or the same, molecular entity. It is the second member of the family of pnictogen bonds, formed by the second member of the pnictogen family of the periodic table. In this overview, we provide the reader with a snapshot of the nature, and possible occurrences, of phosphorus-centered pnictogen bonding in illustrative chemical crystal systems drawn from the ICSD (Inorganic Crystal Structure Database) and CSD (Cambridge Structural Database) databases, some of which date back to the latter part of the last century. The illustrative systems discussed are expected to assist as a guide to researchers in rationalizing phosphorus-centered pnictogen bonding in the rational design of molecular complexes, crystals, and materials and their subsequent characterization.

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Section: Introductionmentioning

confidence: 99%

The Phosphorus Bond, or the Phosphorus-Centered Pnictogen Bond: The Covalently Bound Phosphorus Atom in Molecular Entities and Crystals as a Pnictogen Bond Donor

2022

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“…Pnictogen bonding, unlike other noncovalent interactions, is among the least theoretically and computationally studied chemical interactions [ 1 , 2 , 3 , 4 , 5 , 6 ], yet has been featured in applications in many areas such as catalysis [ 7 , 8 , 9 , 10 ], coordination chemistry [ 3 , 11 , 12 , 13 , 14 , 15 ], photovoltaics [ 16 , 17 ], and supramolecular chemistry [ 4 , 5 ]. There are relatively few reviews [ 3 , 18 , 19 , 20 , 21 , 22 ], original papers (for example [ 1 , 5 , 23 , 24 , 25 , 26 , 27 , 28 , 29 ]), overviews [ 30 ], and comments on the strength [ 31 ], nature [ 32 , 33 ], and propensity of elements of the pnictogen family (Group 15) to engage in pnictogen bonding [ 34 , 35 , 36 ]. The reason for this is probably because recent work on noncovalent interactions has focused largely on exploring σ-hole and π-hole interactions [ 37 , 38 , 39 , 40 , 41 , 42 , …”

Section: Introductionmentioning

confidence: 99%

“…A pnictogen bond features geometric and electronic characteristics akin to those of the hydrogen bond, triel bond (Group 13), tetrel bond (Group 14), chalcogen bond (Group 16), halogen bond (Group 17), arogen bond (Group 18), and other noncovalent interactions, and is therefore regarded as a sister interaction. The importance of pnictogen bonds emerges from its implication in the design and discovery of several functional materials [ 16 , 17 ], such as organic-inorganic halide perovskite semiconductors and in many other areas of materials science [ 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

The Pnictogen Bond: The Covalently Bound Arsenic Atom in Molecular Entities in Crystals as a Pnictogen Bond Donor

Varadwaj

Marques

et al. 2022

Molecules

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In chemical systems, the arsenic-centered pnictogen bond, or simply the arsenic bond, occurs when there is evidence of a net attractive interaction between the electrophilic region associated with a covalently or coordinately bound arsenic atom in a molecular entity and a nucleophile in another or the same molecular entity. It is the third member of the family of pnictogen bonds formed by the third atom of the pnictogen family, Group 15 of the periodic table, and is an inter- or intramolecular noncovalent interaction. In this overview, we present several illustrative crystal structures deposited into the Cambridge Structure Database (CSD) and the Inorganic Chemistry Structural Database (ICSD) during the last and current centuries to demonstrate that the arsenic atom in molecular entities has a significant ability to act as an electrophilic agent to make an attractive engagement with nucleophiles when in close vicinity, thereby forming σ-hole or π-hole interactions, and hence driving (in part, at least) the overall stability of the system’s crystalline phase. This overview does not include results from theoretical simulations reported by others as none of them address the signatory details of As-centered pnictogen bonds. Rather, we aimed at highlighting the interaction modes of arsenic-centered σ- and π-holes in the rationale design of crystal lattices to demonstrate that such interactions are abundant in crystalline materials, but care has to be taken to identify them as is usually done with the much more widely known noncovalent interactions in chemical systems, halogen bonding and hydrogen bonding. We also demonstrate that As-centered pnictogen bonds are usually accompanied by other primary and secondary interactions, which reinforce their occurrence and strength in most of the crystal structures illustrated. A statistical analysis of structures deposited into the CSD was performed for each interaction type As···D (D = N, O, S, Se, Te, F, Cl, Br, I, arene’s π system), thus providing insight into the typical nature of As···D interaction distances and ∠R–As···D bond angles of these interactions in crystals, where R is the remainder of the molecular entity.

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“…Among these noncovalent forces, hydrogen bonding interactions play a central role in noncovalent catalysis [ 2 ] while halogen bonding interactions have lately been exploited as a new tool to catalyze a diverse array of reactions [ 3 – 5 ]. In addition, nonclassical interactions such as anion–π [ 6 – 11 ] as well as chalcogen [ 12 – 17 ] and pnictogen [ 18 – 23 ] bonds were established as emerging driving forces for the development of organic reactions. Very recently, catalysis with carbon bonding interactions was realized and this type of catalysis mode was capable of facilitating a range of typical reactions [ 24 ], thus providing a new platform for organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

A Se···O bonding catalysis approach to the synthesis of calix[4]pyrroles

Tong¹,

Zhao²,

Wang³

2022

Beilstein J. Org. Chem.

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Described herein is a chalcogen bonding catalysis approach to the synthesis of calix[4]pyrrole derivatives. The Se···O bonding interactions between selenide catalysts and ketones gave rise to the catalytic activity in the condensation reactions between pyrrole and ketones, leading to the generation of calix[4]pyrrole derivatives in moderate to high yields. This chalcogen bonding catalysis approach was efficient since only 5 mol % catalyst loading was used to promote the consecutive condensation processes while the reactions could be carried out at room temperature, thus highlighting the potential of this type of nonclassical interactions in catalyzing relative complex transformations.

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On the Importance of Pnictogen and Chalcogen Bonding Interactions in Supramolecular Catalysis

Cited by 50 publications

References 126 publications

The Phosphorus Bond, or the Phosphorus-Centered Pnictogen Bond: The Covalently Bound Phosphorus Atom in Molecular Entities and Crystals as a Pnictogen Bond Donor

The Phosphorus Bond, or the Phosphorus-Centered Pnictogen Bond: The Covalently Bound Phosphorus Atom in Molecular Entities and Crystals as a Pnictogen Bond Donor

The Pnictogen Bond: The Covalently Bound Arsenic Atom in Molecular Entities in Crystals as a Pnictogen Bond Donor

A Se···O bonding catalysis approach to the synthesis of calix[4]pyrroles

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