Chalcogen Bonding "2S-2N Squares" versus Competing Interactions: Exploring the Recognition Properties of Sulfur.
1
Department of ChemistryAllegheny College Meadville PA 16335 USA
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Publication type: Journal Article
Publication date: 2018-12-11
scimago Q1
wos Q2
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
PubMed ID:
30600860
General Chemistry
Catalysis
Organic Chemistry
Abstract
Chalcogen bonding (CB) is the focus of increased attention for its applications in medicinal chemistry, materials science, and crystal engineering. However, the origin of sulfur's recognition properties remains controversial, and experimental evidence for supporting theories is still emerging. Here, a comprehensive evaluation of sulfur CB interactions is presented by investigating 2,1,3-benzothiadiazole X-ray crystallographic structures gathered from the Cambridge Structure Database (CSD), Protein Data Bank (PDB), and own laboratory findings. Through the systematic analysis of substituent effects on a subset library of over thirty benzothiadiazole derivatives, the competing interactions have been categorized into four main classes, namely 2S-2N CB square, halogen bonding (XB), S⋅⋅⋅S, and hydrogen-bonding (HB). A geometric model is employed to characterize the 2S-2N CB square motifs and discuss the role of electrostatic, dipole, and orbital contributions toward the interaction.
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Ams M. R. et al. Chalcogen Bonding "2S-2N Squares" versus Competing Interactions: Exploring the Recognition Properties of Sulfur. // Chemistry - A European Journal. 2018. Vol. 25. No. 1. pp. 323-333.
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Ams M. R., Trapp N., Schwab A., Milić J., Diederich F. Chalcogen Bonding "2S-2N Squares" versus Competing Interactions: Exploring the Recognition Properties of Sulfur. // Chemistry - A European Journal. 2018. Vol. 25. No. 1. pp. 323-333.
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TY - JOUR
DO - 10.1002/chem.201804261
UR - https://doi.org/10.1002/chem.201804261
TI - Chalcogen Bonding "2S-2N Squares" versus Competing Interactions: Exploring the Recognition Properties of Sulfur.
T2 - Chemistry - A European Journal
AU - Ams, Mark R
AU - Trapp, Nils
AU - Schwab, Anatol
AU - Milić, J.
AU - Diederich, Francois
PY - 2018
DA - 2018/12/11
PB - Wiley
SP - 323-333
IS - 1
VL - 25
PMID - 30600860
SN - 0947-6539
SN - 1521-3765
ER -
Cite this
BibTex (up to 50 authors)
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@article{2018_Ams,
author = {Mark R Ams and Nils Trapp and Anatol Schwab and J. Milić and Francois Diederich},
title = {Chalcogen Bonding "2S-2N Squares" versus Competing Interactions: Exploring the Recognition Properties of Sulfur.},
journal = {Chemistry - A European Journal},
year = {2018},
volume = {25},
publisher = {Wiley},
month = {dec},
url = {https://doi.org/10.1002/chem.201804261},
number = {1},
pages = {323--333},
doi = {10.1002/chem.201804261}
}
Cite this
MLA
Copy
Ams, Mark R., et al. “Chalcogen Bonding "2S-2N Squares" versus Competing Interactions: Exploring the Recognition Properties of Sulfur..” Chemistry - A European Journal, vol. 25, no. 1, Dec. 2018, pp. 323-333. https://doi.org/10.1002/chem.201804261.