Definition of the Pnictogen Bond: A Perspective
Abstract
:1. Preface
2. Definition and Recommendations
- A pnictogen bond occurs in chemical systems when there is evidence of a net attractive interaction between an electrophilic region associated with a pnictogen atom in a molecular entity and a nucleophilic region in another, or the same molecular entity.
- Note 1: A pnictogen bond is usually represented by three dots in the geometric motif R–Pn···A, where Pn is the PnB donor, representing any pnictogen atom (possibly hypervalent) that has an electrophilic region on it; R is the remaining part of the molecular entity R–Pn containing the PnB donor; A is a PnB acceptor, which may or may not represent a molecular entity, but that has at least one nucleophilic region.
- Note 2: An electrophilic site on the PnB donor Pn generally refers to the lowest electron density region, while a nucleophilic site on the PnB acceptor A usually refers to the highest electron density region, and the resulting interactions formed between the two entities exhibit different directional features and complementarity.
- Note 3: At an equilibrium configuration, PnB donors Pn exhibit the ability to act as electron density acceptors, and PnB acceptors A exhibit the ability to act as electron density donors.
- Note 4: A pnictogen bond may occur within a neutral molecule [12,14] or between two neutral molecules in close proximity [12,13]; it can also occur between a neutral molecule with a PnB donor Pn and an anion containing A [15]; between a PnB donor in a molecular cation and a nucleophile (or negative π-density) A on a neutral molecule [16]; between an electron-poor delocalized region (positive π-density) as the PnB donor Pn and nucleophile A (or negative π-density) on the acceptor entity; or between two molecular entities of opposite charge polarity (i.e., an ion pair)) with a PnB donor and a PnB acceptor [7,17,18].
- Note 6: Because of its variable electrostatic character, a pnictogen atom in a molecular entity may engage in a number of interactions that lead to the appearance of a variety electronic and geometric features [6,7,11,12,13,14,19]. The term pnictogen bond should not be used for attractive interactions in which the pnictogen atom (frequently nitrogen and sometimes phosphorous) functions as a nucleophile.
- Note 7: The electrophilic and nucleophilic characteristics of a bound pnictogen atom and its PnB forming ability may be found by searching for the local minima and maxima of the potential on the electrostatic surface of the molecular entity [6,7,11,12,13,14,20,21,22,23,24,25,26,27,28]. The electrophilic region on the surface of the bound pnictogen atom along the outermost extension of the R–Pn covalent or coordinate bond in an isolated monomeric entity is often (but not always) represented by a local maximum of the potential and may be used to search for pnictogen bonds between it and the nucleophilic regions on atoms in the entities with which it interacts [6,7,11,12,13,14,20,21,22,23,24,25,26,27,28].
- Note 8: Two pnictogen atoms in two different molecular entities may be involved in an attractive engagement to form a pnictogen bond, in which case, one of the pnictogen atoms must act as a pnictogen bond donor, and that in the partner molecular entity must act as a PnB acceptor, such as in NO2HP···NH3 [29].
- Note 9: The pnictogen bond should be viewed as an attractive interaction between PnB donor site Pn and PnB acceptor site A of opposite charge polarity (Pnδ+ and Aδ−), resulting in a coulombic interaction between them; the charge polarity δ+ and δ− symbolically refers to the local charge polarity on the interacting regions on Pn and A, respectively.
- Note 10: The pnictogen bond should follow the Type-II topology of non-covalent bonding interactions; a Type-II interaction, R–Pn···A, is often linear or quasi-linear (but may be non-linear) and satisfies Note 9.
3. Some Common Pnictogen Bond Donors and Acceptors
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- A pnictogen in a trihalide: PnX3 (Pn = N, P, As, Sb, Bi; X = halide).
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- The Nβ of covalently bonded azides, such as –Nα = Nβ = Nγ (as in 2,4,6-triazidoborazine (H3B3N12) [35], 5-diazonio-4-(2H-tetrazol-5-yl)-1,2,3-triazol-1-ide (C3HN9) [36]), and 2,2,4,4,6,6-hexaazido-2,4,6-triphospha-1,3,5-triazine (P3N21) [37], or nitrogen in the diazonio fragment, such as in –Nα = Nβ (as in 4-diazonio-3,5-dinitropyrazol-1-ide (C3N6O4) [38] and in diazonionaphthalen-1-olate (C10H6N2O) [39].
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- The nitrogen in ammonium, diammonium, and (chain and arene) derivatives of ammonium (for example, NH4+, NH3NH32+, NH3NH2+, CH3NH3+, [CnH2n+1NH3]+ (n = 2, 3, …, 18), and [NH3(CH2)mNH3]2+ (m = 2, 3, …, 8) [7]).
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- The phosphorous in phosphoryl halides (POF3, POCl3, and POBr3) [11]; phosphorus(V) triazides OP(N3)3 and SP(N3)3 [52]; diphosphorus tetraiodide P2I4, phosphorus tricyanide, P(CN)3, and 4,4′,4″-phosphinetriyltripyridine [53]; and disphospha-functionalised naphthalenes (such as Nap(PCl2)2 Nap(PBr2)2 and Nap(PI)2 (Nap = naphthalene-1,8-diyl) [54]) and phosphorus diisocyanate chloride P(CO)2 [55], etc.
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- Phosphorous in derivatives of halo-substituted phosphazenes (viz. cyclo-tetrakis(difluorophosphazene) F8N4P4 [56], decafluorocyclo-pentaphosphazene F10N5P5 [57], hexachloro-cyclo-triphosphazene Cl6N3P3 [58], cyclo-tetrakis(phosphorus(V) nitride dichloride) Cl8N4P4 [59], nonachlorohexahydroheptaazahexaphosphaphenalene Cl9N7P6 [60], tris(dibromophosphazene) Br6N3P3 [61], octabromocyclo-tetraphosphazene Br8N4P4, [62], etc.).
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- Phosphorous in phosphorus oxides (phosphorus(V) oxide P2O5 [63], tetraphosphorus(III) oxide P4O6 [64], tetraphosphorus(III,IV) heptaoxide P4O7 [65], phosphorus(II) oxide P4O8 [66], tetraphosphorus(II,III) nonaoxide oxide P4O9 [67], tetraphosphorus(V) oxide P4O10 [68], phosphorus ozonide P4O18 [69], etc.).
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- Pnictogen in halide-, amino-, imidazole-, oxy-, and thio-substituted heavier pnictogen derivatives, in diaryl halido-substituted bismuthanes (e.g., C24H34BiI [70]), and in BiMe3Cl2, AsMe3, SbMe3, BiMe3, etc.).
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- The antimony in bis(dimethylstibanyl)sulfane [76], bis(dimethylstibanyl)oxane [76], (trimethyl-stibino)-dimethyl-stibonium [77], trichloro-dipyridine-antimony [78], triphenyl-bis(p-tolylacetato)-antimony [79], bis(3-methoxyphenylacetate)-triphenyl-antimony [79], bis(acetato-O)-(2,6-bis(t-butoxymethyl)phenyl-C)-antimony(III) [80], bis(trichloro-antimony) [81], etc.
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- Arene-substituted pnictogen derivatives, including the bismuth in triphenyl-bismuth Bi(C6H5)3 and pyridine dipyrrolide complexes, C43H37BiIN3, etc.
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- A positive π system (species featuring a double or triple bond (e.g., midpoint of the N≡N bond in N2; P in P2; Bi in Bi2; N in NO2) of neutral and cationic entities).
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- A lone pair on an atom in a molecule. There are almost limitless possibilities, for example, the N in pyridines or amines, or even in N2; the O in H2O, CO, CO2, an ether, or a carbonyl group, or a phosphorus oxide; covalently bonded halogens in molecules; As in AsMe3; a chalcogen in a heterocycle such as a thio-, seleno-, and tellurophene derivatives as well as fused polycyclic derivatives thereof; furoxans, 2,5-thiadiazoles N-oxides, sulfoxide, aryl sulfoxides, and tellurazoles N-oxides; derivatives of macrocyclic crown-ethers such as 18-crown-6, 15-crown-5 and 21-crown-7, etc.
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- Many anions, such as halide anions; NO3−; CF3SO3−; BF4−; tetraphenylborate C24H20B−; ClO4−; 5-oxotetrazole CHN4O−; I3−; Br3−; N3−; BF4−; AuCl4−; PF6−; AsF6−; pentazolide N5−; 5,5′-bistetrazolates C2N82−; p-tosylate C7H7SO3−; polyatomic oxyanions such as C2O42−; GaCl4−; ZnCl42−; ReO4−; AsCl4−, SbCl4−; BiCl4−; etc.
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- A (negative) π system (species featuring a double or triple bond) and arene moieties of any kind, such as the centroid of the arenes and the midpoints of molecular As2 and N in NO3−, etc.
4. Examples of Chemical Systems Featuring Pnictogen Bonding
5. A List of Characteristic Features
- The separation distance between the PnB donor atom Pn and the nucleophilic site of PnB acceptor A tends to be smaller than the sum of the van der Waals radii of the respective interacting atomic basins [6,7,11,12,13,14] and larger than the sum of their covalent bond radii [2,3,4]; the deviation of the former is likely since the known van der Waals radii of atoms are only accurate with ±0.2 Å [13,113,114];
- The PnB donor site on Pn tends to approach the PnB acceptor site A along the outer extension of a σ covalent or coordinate bond, and the angular deviation from the extension is often more pronounced in PnBs [6,7,11,12,13,14] than in halogen bonds, as in ChBs [4], with the latter possibly being due to the involvement of secondary interactions;
- The angle of interaction, ∠R–Pn···A, tends to be linear or quasi-linear when the approach of the electrophile on Pn is along the σ covalent/coordinate bond extension, but this can be non-linear or have a bent shape when the pnictogen bond occurs between an electron density-deficient (electrophilic) π-type orbital of the bonded pnictogen atom and the nucleophilic region on A [6,7,11,12,13,14] or when secondary interactions are involved;
- The distance of the R–Pn covalent bond opposite to the PnB in a molecular adduct is typically longer than that in the isolated (unbound) PnB donor;
- The infrared absorption and Raman scattering observables of both R–Pn and A are affected by PnB formation; the vibrational frequency of the R–Pn bond may be red-shifted or blue-shifted depending on the extent of the interactions involved compared to the frequency of the same bond in the isolated molecular entity; new vibrational modes associated with the formation of the Pn···A intermolecular pnictogen bond should also be characteristically observed [116,117], as observed for ChBs;
- The UV–vis absorption bands of the PnB donor chromophore may experience a shift to longer wavelengths [128];
- At least some transfer of charge density from the frontier PnB acceptor orbital to the frontier PnB donor orbital may occur [15,129,130]; when the transfer of electron charge density between them is significant, the formation of a dative coordinate interaction is likely [131]; the occurrence of the IUPAC-recommended phenomena for HBs (see Criteria E1 and Characteristic C5 of Ref. [2]) is also applicable to XBs [132,133,134,135] and ChBs [136,137,138];
- The PnB strength typically decreases with a given acceptor A, as the electronegativity of Pn increases in the order Bi < Sb < As < P < N, and the electron withdrawing ability of R decreases;
- The PnB bond strength increases for a specific PnB acceptor A and the remaining R, as the polarizability of the pnictogen atoms in the molecular entities increases (Bi > Sb > As > P > N) [15]. This is the same as what is observed for the halogen derivative forming XB (I > Br > Cl > F) [145,146] and the chalcogen derivatives forming ChB (Te > Se > S > O) [147]. However, if secondary interactions (e.g., a hydrogen bond, halogen bond, chalcogen bond, tetrel bond, etc.) are simultaneously involved with either the PnB donor or PnB acceptor, the order of interaction strength may also be altered;
6. Concluding Remarks
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
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Varadwaj, A.; Varadwaj, P.R.; Marques, H.M.; Yamashita, K. Definition of the Pnictogen Bond: A Perspective. Inorganics 2022, 10, 149. https://doi.org/10.3390/inorganics10100149
Varadwaj A, Varadwaj PR, Marques HM, Yamashita K. Definition of the Pnictogen Bond: A Perspective. Inorganics. 2022; 10(10):149. https://doi.org/10.3390/inorganics10100149
Chicago/Turabian StyleVaradwaj, Arpita, Pradeep R. Varadwaj, Helder M. Marques, and Koichi Yamashita. 2022. "Definition of the Pnictogen Bond: A Perspective" Inorganics 10, no. 10: 149. https://doi.org/10.3390/inorganics10100149