A Structural Approach to the Strength Evaluation of Linear Chalcogen Bonds

Maria Carla Aragoni; Massimiliano Arca; Vito Lippolis; Anna Pintus; Yury Torubaev; Enrico Podda

doi:10.3390/molecules28073133

A Structural Approach to the Strength Evaluation of Linear Chalcogen Bonds

Maria Carla Aragoni, Massimiliano Arca, Vito Lippolis, Anna Pintus, Yury Torubaev, Enrico Podda

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

The experimental structural features of chalcogen bonding (ChB) interactions in over 34,000 linear fragments R–Ch⋯A (Ch = S, Se, Te; R = C, N, O, S, Se, Te; A = N, O, S, Se, Te, F, Cl, Br, I) were analyzed. The bond distances d_R–Ch and the interaction distances d_Ch⋯A were investigated, and the functions δ_R–Ch and δ_Ch⋯A were introduced to compare the structural data of R–Ch⋯A fragments involving different Ch atoms. The functions δ_R−Ch and δ_Ch⋯A were calculated by normalizing the differences between the relevant bond d_R–Ch and ChB interaction d_Ch⋯A distances with respect to the sum of the relevant covalent (r_covR + r_covCh) and the van der Waals (vdW) radii (r_vdWCh + r_vdWA), respectively. A systematic comparison is presented, highlighting the role of the chalcogen involved, the role of the R atoms covalently bonded to the Ch, and the role of the A species playing the role of chalcogen bond acceptor. Based on the results obtained, an innovative approach is proposed for the evaluation and categorization of the ChB strength based on structural data.

Original language	English
Article number	3133
Journal	Molecules
Volume	28
Issue number	7
DOIs	https://doi.org/10.3390/molecules28073133
State	Published - 1 Apr 2023

Keywords

chalcogen bonding
crystallographic distances
selenium
structural data
sulfur
tellurium

ASJC Scopus subject areas

Drug Discovery
Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Physical and Theoretical Chemistry
Pharmaceutical Science
Organic Chemistry

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10.3390/molecules28073133

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title = "A Structural Approach to the Strength Evaluation of Linear Chalcogen Bonds",

abstract = "The experimental structural features of chalcogen bonding (ChB) interactions in over 34,000 linear fragments R–Ch⋯A (Ch = S, Se, Te; R = C, N, O, S, Se, Te; A = N, O, S, Se, Te, F, Cl, Br, I) were analyzed. The bond distances dR–Ch and the interaction distances dCh⋯A were investigated, and the functions δR–Ch and δCh⋯A were introduced to compare the structural data of R–Ch⋯A fragments involving different Ch atoms. The functions δR−Ch and δCh⋯A were calculated by normalizing the differences between the relevant bond dR–Ch and ChB interaction dCh⋯A distances with respect to the sum of the relevant covalent (rcovR + rcovCh) and the van der Waals (vdW) radii (rvdWCh + rvdWA), respectively. A systematic comparison is presented, highlighting the role of the chalcogen involved, the role of the R atoms covalently bonded to the Ch, and the role of the A species playing the role of chalcogen bond acceptor. Based on the results obtained, an innovative approach is proposed for the evaluation and categorization of the ChB strength based on structural data.",

keywords = "chalcogen bonding, crystallographic distances, selenium, structural data, sulfur, tellurium",

author = "Aragoni, {Maria Carla} and Massimiliano Arca and Vito Lippolis and Anna Pintus and Yury Torubaev and Enrico Podda",

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doi = "10.3390/molecules28073133",

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AU - Aragoni, Maria Carla

AU - Arca, Massimiliano

AU - Lippolis, Vito

AU - Pintus, Anna

AU - Torubaev, Yury

AU - Podda, Enrico

PY - 2023/4/1

Y1 - 2023/4/1

N2 - The experimental structural features of chalcogen bonding (ChB) interactions in over 34,000 linear fragments R–Ch⋯A (Ch = S, Se, Te; R = C, N, O, S, Se, Te; A = N, O, S, Se, Te, F, Cl, Br, I) were analyzed. The bond distances dR–Ch and the interaction distances dCh⋯A were investigated, and the functions δR–Ch and δCh⋯A were introduced to compare the structural data of R–Ch⋯A fragments involving different Ch atoms. The functions δR−Ch and δCh⋯A were calculated by normalizing the differences between the relevant bond dR–Ch and ChB interaction dCh⋯A distances with respect to the sum of the relevant covalent (rcovR + rcovCh) and the van der Waals (vdW) radii (rvdWCh + rvdWA), respectively. A systematic comparison is presented, highlighting the role of the chalcogen involved, the role of the R atoms covalently bonded to the Ch, and the role of the A species playing the role of chalcogen bond acceptor. Based on the results obtained, an innovative approach is proposed for the evaluation and categorization of the ChB strength based on structural data.

AB - The experimental structural features of chalcogen bonding (ChB) interactions in over 34,000 linear fragments R–Ch⋯A (Ch = S, Se, Te; R = C, N, O, S, Se, Te; A = N, O, S, Se, Te, F, Cl, Br, I) were analyzed. The bond distances dR–Ch and the interaction distances dCh⋯A were investigated, and the functions δR–Ch and δCh⋯A were introduced to compare the structural data of R–Ch⋯A fragments involving different Ch atoms. The functions δR−Ch and δCh⋯A were calculated by normalizing the differences between the relevant bond dR–Ch and ChB interaction dCh⋯A distances with respect to the sum of the relevant covalent (rcovR + rcovCh) and the van der Waals (vdW) radii (rvdWCh + rvdWA), respectively. A systematic comparison is presented, highlighting the role of the chalcogen involved, the role of the R atoms covalently bonded to the Ch, and the role of the A species playing the role of chalcogen bond acceptor. Based on the results obtained, an innovative approach is proposed for the evaluation and categorization of the ChB strength based on structural data.

KW - chalcogen bonding

KW - crystallographic distances

KW - selenium

KW - structural data

KW - sulfur

KW - tellurium

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JO - Molecules

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A Structural Approach to the Strength Evaluation of Linear Chalcogen Bonds

Abstract

Keywords

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