Nature of S<sub>2</sub>Se<sub>2</sub> σ(4c–6e) at naphthalene 1,8-positions and models, elucidated by QTAIM dual functional analysis

Nakanishi, Warō; Tsubomoto, Yutaka; Hayashi, Satoko

doi:10.1039/c6ra17767k

Cited by 12 publications

(8 citation statements)

References 77 publications

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“…A substantial number of compounds containing (4c-6e) have been reported (Nakanishi, 2006;Nakanishi & Hayashi, 2013a). The (4c-6e) interactions are strongly suggested to play an important role in the development of high functionalities in materials and in the key processes of biological and/or pharmaceutical activities (Nakanishi et al, 2002(Nakanishi et al, , 2003(Nakanishi et al, , 2004(Nakanishi et al, , 2016Nakanishi, 2006Nakanishi, , 2013aRappoport, 2013).…”

Section: Introductionmentioning

confidence: 99%

Nature ofE₂X₂σ(4c–6e) of theX---E—E---Xtype at naphthalene 1,8-positions and model, elucidated by X-ray crystallographic analysis and QC calculations with the QTAIM approach

Tsubomoto

Hayashi

Nakanishi

et al. 2017

Acta Crystallogr Sect B

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The nature of EX σ(4c-6e) of the X-*-E-*-E-*-X type is elucidated for 1-(8-XCH)E-E(CHX-8')-1' [(1) E, X = S, Cl; (2) S, Br; (3) Se, Cl; (4) Se, Br] after structural determination of (1), (3) and (4), together with model A [MeX---E(H)-E(H)---XMe (E = S and Se; X = Cl and Br)]. The quantum theory of atoms-in-molecules dual functional analysis (QTAIM-DFA) is applied. The total electron energy densities H(r) are plotted versus H(r) - V(r)/2 for the interactions at the bond critical points (BCPs; *), where V(r) show the potential energy densities at the BCPs. Data for the perturbed structures around the fully optimized structures are employed for the plots, in addition to those of the fully optimized structures. The plots were analysed using the polar coordinate (R, θ) representation of the data of the fully optimized structures. Data containing the perturbed structures were analysed by (θ, κ), where θ corresponds to the tangent line of the plot and κ is the curvature. Whereas (R, θ) shows the static nature, (θ, κ) represents the dynamic nature of interactions. E-*-E are all classified as shared shell (S) interactions for (1)-(4) and as weak covalent (Cov-w) in nature (S/Cov-w). The nature of pure CS (closed shell)/typical-HB (hydrogen bond) with no covalency is predicted for E-*-X in (1) and (3), regular CS/typical-HB nature with covalency is predicted for (4), and an intermediate nature is predicted for (2). The NBO energies evaluated for E-*-X in (1)-(4) are substantially larger than those in model A due the shortened length at the naphthalene 1,8-positions. The nature of EX of σ(4c-6e) is well elucidated via QTAIM-DFA.

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Section: Introductionmentioning

confidence: 99%

Nature ofE₂X₂σ(4c–6e) of theX---E—E---Xtype at naphthalene 1,8-positions and model, elucidated by X-ray crystallographic analysis and QC calculations with the QTAIM approach

Tsubomoto

Hayashi

Nakanishi

et al. 2017

Acta Crystallogr Sect B

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“…6), (Se, S: 7) and (Se, Se: 8), aer preparation and structural determination of 8. 13 The static nature of A E 2 B E 2 s(4c-6e) has also been reported for 1-4 based on the observed crystal structures. [13][14][15][16] A E 2 B E 2 s(4c-6e) are also recognized as a form of chalcogen bonding.…”

Section: -46-12mentioning

confidence: 92%

High-resolution X-ray diffraction determination of the electron density of 1-(8-PhSC₁₀H₆)SS(C₁₀H₆SPh-8′)-1′ with the QTAIM approach: evidence for S₄ σ(4c–6e) at the naphthalene peri-positions

et al. 2018

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“…A E---B E of A E 2 B E 2 σ(4c-6e) has been elucidated [24][25][26][27] using the quantum theory of atoms in molecules (QTAIM) approach, introduced by Bader [28][29][30][31][32][33][34][35][36][37]. e linear interactions of the σ(4c-6e) type will form if B E in A E 2 B E 2 is replaced by X, giving E 2 X 2 σ(4c-6e).…”

Section: E Nature Of B E---a E and A E-a E In B E---a E-mentioning

confidence: 99%

Dynamic and Static Nature of Br₄σ(4c–6e) and Se₂Br₅σ(7c–10e) in the Selenanthrene System and Related Species Elucidated by QTAIM Dual Functional Analysis with QC Calculations

Hayashi

Nishide

Nakanishi

2020

Bioinorganic Chemistry and Applications

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The nature of Br4σ(4c–6e) of the BBr-∗-ABr-∗-ABr-∗-BBr form is elucidated for SeC12H8(Br)SeBr---Br-Br---BrSe(Br)C12H8Se, the selenanthrene system, and the models with QTAIM dual functional analysis (QTAIM-DFA). Asterisks (∗) are employed to emphasize the existence of bond critical points on the interactions in question. Data from the fully optimized structure correspond to the static nature of interactions. In our treatment, data from the perturbed structures, around the fully optimized structure, are employed for the analysis, in addition to those from the fully optimized one, which represent the dynamic nature of interactions. The ABr-∗-ABr and ABr-∗-BBr interactions are predicted to have the CT-TBP (trigonal bipyramidal adduct formation through charge transfer) nature and the typical hydrogen bond nature, respectively. The nature of Se2Br5σ(7c–10e) is also clarified typically, employing an anionic model of [Br-Se(C4H4Se)-Br---Br---Br-Se(C4H4Se)-Br]−, the 1,4-diselenin system, rather than (BrSeC12H8)Br---Se---Br-Br---Br-Se(C12H8Se)-Br, the selenanthrene system.

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Nature of S₂Se₂ σ(4c–6e) at naphthalene 1,8-positions and models, elucidated by QTAIM dual functional analysis

Abstract: The nature of BE––AE––AE––BE σ(4c–6e) is primarily elucidated at naphthalene 1,8-positions: while the weak covalent nature is predicted for all AE––AE, the HB nature with covalency or the CT-MC (MC formation through CT) nature is for AE–*–BE.

Cited by 12 publications

References 77 publications

Nature ofE₂X₂σ(4c–6e) of theX---E—E---Xtype at naphthalene 1,8-positions and model, elucidated by X-ray crystallographic analysis and QC calculations with the QTAIM approach

Nature ofE₂X₂σ(4c–6e) of theX---E—E---Xtype at naphthalene 1,8-positions and model, elucidated by X-ray crystallographic analysis and QC calculations with the QTAIM approach

High-resolution X-ray diffraction determination of the electron density of 1-(8-PhSC₁₀H₆)SS(C₁₀H₆SPh-8′)-1′ with the QTAIM approach: evidence for S₄ σ(4c–6e) at the naphthalene peri-positions

Dynamic and Static Nature of Br₄σ(4c–6e) and Se₂Br₅σ(7c–10e) in the Selenanthrene System and Related Species Elucidated by QTAIM Dual Functional Analysis with QC Calculations

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Nature of S2Se2 σ(4c–6e) at naphthalene 1,8-positions and models, elucidated by QTAIM dual functional analysis

Abstract: The nature of BE–*–AE–*–AE–*–BE σ(4c–6e) is primarily elucidated at naphthalene 1,8-positions: while the weak covalent nature is predicted for all AE–*–AE, the HB nature with covalency or the CT-MC (MC formation through CT) nature is for AE–*–BE.

Cited by 12 publications

References 77 publications

Nature ofE2X2σ(4c–6e) of theX---E—E---Xtype at naphthalene 1,8-positions and model, elucidated by X-ray crystallographic analysis and QC calculations with the QTAIM approach

Nature ofE2X2σ(4c–6e) of theX---E—E---Xtype at naphthalene 1,8-positions and model, elucidated by X-ray crystallographic analysis and QC calculations with the QTAIM approach

High-resolution X-ray diffraction determination of the electron density of 1-(8-PhSC10H6)SS(C10H6SPh-8′)-1′ with the QTAIM approach: evidence for S4 σ(4c–6e) at the naphthalene peri-positions

Dynamic and Static Nature of Br4σ(4c–6e) and Se2Br5σ(7c–10e) in the Selenanthrene System and Related Species Elucidated by QTAIM Dual Functional Analysis with QC Calculations

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Nature of S₂Se₂ σ(4c–6e) at naphthalene 1,8-positions and models, elucidated by QTAIM dual functional analysis

Abstract: The nature of BE––AE––AE––BE σ(4c–6e) is primarily elucidated at naphthalene 1,8-positions: while the weak covalent nature is predicted for all AE––AE, the HB nature with covalency or the CT-MC (MC formation through CT) nature is for AE–*–BE.

Nature ofE₂X₂σ(4c–6e) of theX---E—E---Xtype at naphthalene 1,8-positions and model, elucidated by X-ray crystallographic analysis and QC calculations with the QTAIM approach

Nature ofE₂X₂σ(4c–6e) of theX---E—E---Xtype at naphthalene 1,8-positions and model, elucidated by X-ray crystallographic analysis and QC calculations with the QTAIM approach

High-resolution X-ray diffraction determination of the electron density of 1-(8-PhSC₁₀H₆)SS(C₁₀H₆SPh-8′)-1′ with the QTAIM approach: evidence for S₄ σ(4c–6e) at the naphthalene peri-positions

Dynamic and Static Nature of Br₄σ(4c–6e) and Se₂Br₅σ(7c–10e) in the Selenanthrene System and Related Species Elucidated by QTAIM Dual Functional Analysis with QC Calculations