Pnicogen–pnicogen interactions in O2XP:PH2Y complexes (X=H, F, CN; Y=H, OH, OCH3, CH3, NH2)

Esrafili, Mehdi D.; Mohammadian-Sabet, Fariba

doi:10.1016/j.cplett.2015.08.045

Cited by 23 publications

(10 citation statements)

References 53 publications

(55 reference statements)

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“…Most of these papers were calculated at the MP2/aug'-cc-pVTZ basis set. We and others have found that FPH2 and related YPH2 (Y = H, OH, OCH3, CH3, NH2) and FH2X (X = P, As) are strong and directional Lewis acid especially suited for theoretical studies [154][155][156]. Highly acidic heteroboranes yield strong pnictogen bonds [157].…”

Section: Pnictogen Bondsmentioning

confidence: 99%

Not Only Hydrogen Bonds: Other Noncovalent Interactions

2020

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In this review, we provide a consistent description of noncovalent interactions, covering most groups of the Periodic Table. Different types of bonds are discussed using their trivial names. Moreover, the new name “Spodium bonds” is proposed for group 12 since noncovalent interactions involving this group of elements as electron acceptors have not yet been named. Excluding hydrogen bonds, the following noncovalent interactions will be discussed: alkali, alkaline earth, regium, spodium, triel, tetrel, pnictogen, chalcogen, halogen, and aerogen, which almost covers the Periodic Table entirely. Other interactions, such as orthogonal interactions and π-π stacking, will also be considered. Research and applications of σ-hole and π-hole interactions involving the p-block element is growing exponentially. The important applications include supramolecular chemistry, crystal engineering, catalysis, enzymatic chemistry molecular machines, membrane ion transport, etc. Despite the fact that this review is not intended to be comprehensive, a number of representative works for each type of interaction is provided. The possibility of modeling the dissociation energies of the complexes using different models (HSAB, ECW, Alkorta-Legon) was analyzed. Finally, the extension of Cahn-Ingold-Prelog priority rules to noncovalent is proposed.

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Section: Pnictogen Bondsmentioning

confidence: 99%

Not Only Hydrogen Bonds: Other Noncovalent Interactions

2020

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“…In the last decade, chalcogen bond interactions have been the subject of numerous experimental and theoretical studies. Several types of chalcogen bonds, including conventional (e.g., S⋅⋅⋅O or S⋅⋅⋅N interactions), chalcogen hydride, and single‐electron chalcogen bond interactions have been reported. The chalcogen–chalcogen bond is an attractive intramolecular or intermolecular interaction, arising from the close approach of an electrophilic and a nucleophilic chalcogen atom.…”

Section: Introductionmentioning

confidence: 99%

Homonuclear chalcogen–chalcogen bond interactions in complexes pairing YO₃ and YHX molecules (Y = S, Se; X = H, Cl, Br, CCH, NC, OH, OCH₃): Influence of substitution and cooperativity

Esrafili

Mohammadian-Sabet

2016

Int J of Quantum Chemistry

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MP2/aug-cc-pVTZ calculations are performed on complexes of YO 3 (Y 5 S, Se) with a series of electron-donating chalcogen bases YHX (X 5 H, Cl, Br, CCH, NC, OH, OCH 3 ). These complexes are formed through the interaction of a positive electrostatic potential region (p-hole) on the YO 3 molecule with the negative region in YHX. Interaction energies of the binary O 3 YÁÁÁYHX complexes are in the range of 24.37 to 212.09 kcal/mol. The quantum theory of atoms in molecules and the natural bond orbital analysis were applied to characterize the nature of interactions. It was found that the formation and stability of these binary complexes are ruled mainly by electro-static effects, although the electron charge transfer from YHX to YO 3 unit also seems to play an important role. In addition, mutual influence between the YÁÁÁN and YÁÁÁY interactions is studied in the ternary HCNÁÁÁO 3 YÁÁÁYHX complexes. The results indicate that the formation of a YÁÁÁN interaction tends to weaken YÁÁÁY bond in the ternary systems. Although the YÁÁÁY interaction is weaker than the YÁÁÁN one, however, both types of interactions seem to compete with each other in the HCNÁÁÁO 3 YÁÁÁYHX complexes.

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“…Pnicogen bonds exhibit cooperativity with H-bonds, as noted in complexes of π-electron systems such as benzene with PCl 3 [65]. There have been some studies of π-hole pnicogen bonds, but those studies focused on the hypervalent PO 2 Cl molecule [76], PO 2 R [77], or the (H 2 C=PH 2 ) + ion [78], none of which can contain a σ-hole. π-Hole pnicogen bonds have been identified in unconventional bonding situations such as NNO [79], but these are quite weak and there is no competing σ-hole interaction.…”

Section: Introductionmentioning

confidence: 99%

On the ability of pnicogen atoms to engage in both σ and π-hole complexes. Heterodimers of ZF2C6H5 (Z = P, As, Sb, Bi) and NH3

et al. 2019

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When bound to a pair of F atoms and a phenyl ring, a pyramidal pnicogen (Z) atom can form a pnicogen bond wherein an NH 3 base lies opposite one F atom. In addition to this σ-hole complex, the ZF 2 C 6 H 5 molecule can distort in such a way that the NH 3 approaches on the opposite side to the lone pair on Z, where there is a so-called π-hole. The interaction energies of these π-hole dimers are roughly 30 kcal/mol, much larger than the equivalent quantities for the σ-hole complexes, which are only 4-13 kcal/ mol. On the other hand, this large interaction energy is countered by the considerable deformation energy required for the Lewis acid to adopt the geometry necessary to form the π-hole complex. The overall energetics of the complexation reaction are thus more exothermic for the σ-hole dimers than for the π-hole dimers.

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Pnicogen–pnicogen interactions in O2XP:PH2Y complexes (X=H, F, CN; Y=H, OH, OCH3, CH3, NH2)

Cited by 23 publications

References 53 publications

Not Only Hydrogen Bonds: Other Noncovalent Interactions

Not Only Hydrogen Bonds: Other Noncovalent Interactions

Homonuclear chalcogen–chalcogen bond interactions in complexes pairing YO₃ and YHX molecules (Y = S, Se; X = H, Cl, Br, CCH, NC, OH, OCH₃): Influence of substitution and cooperativity

On the ability of pnicogen atoms to engage in both σ and π-hole complexes. Heterodimers of ZF2C6H5 (Z = P, As, Sb, Bi) and NH3

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Pnicogen–pnicogen interactions in O2XP:PH2Y complexes (X=H, F, CN; Y=H, OH, OCH3, CH3, NH2)

Cited by 23 publications

References 53 publications

Not Only Hydrogen Bonds: Other Noncovalent Interactions

Not Only Hydrogen Bonds: Other Noncovalent Interactions

Homonuclear chalcogen–chalcogen bond interactions in complexes pairing YO3 and YHX molecules (Y = S, Se; X = H, Cl, Br, CCH, NC, OH, OCH3): Influence of substitution and cooperativity

On the ability of pnicogen atoms to engage in both σ and π-hole complexes. Heterodimers of ZF2C6H5 (Z = P, As, Sb, Bi) and NH3

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Homonuclear chalcogen–chalcogen bond interactions in complexes pairing YO₃ and YHX molecules (Y = S, Se; X = H, Cl, Br, CCH, NC, OH, OCH₃): Influence of substitution and cooperativity