Evidence map›Paper›PMID 32227661›Full record

ArticleAngewandte Chemie (International ed. in English)2020

"Anti-Electrostatic" Halogen Bonding.

Jana M Holthoff, Elric Engelage, Robert Weiss, Stefan M Huber

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.

0numbers the graph read from it
0cells of the map it votes in
19citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

19 citing papers in PubMed.

  1. Article
  2. Article
  3. Review
  4. Diverse Cyclization Pathways Between Nitriles with ActiveInternational journal of molecular sciences · 2024
    Article
  5. Article
  6. Article
  7. A Potent Auto-Umpolung Ligand for Conjugative Radical Stabilization.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023
    Article
  8. Crystal structure ofActa crystallographica. Section E, Crystallographic communications · 2022
    Article
  9. The Role of Hydrogen Bonds in Interactions between [PdClMolecules (Basel, Switzerland) · 2022
    Article
  10. Review
  11. Article
  12. Article
  13. "Anti-electrostatic" Halogen Bonding between Ions of Like Charge.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021
    Article
  14. Anion⋅⋅⋅Anion Interactions Involving σ-Holes of Perrhenate, Pertechnetate and Permanganate Anions.Chemphyschem : a European journal of chemical physics and physical chemistry · 2021
    Article
  15. Article
  16. Article
  17. Article
  18. Article
  19. "Anti-Electrostatic" Halogen Bonding.Angewandte Chemie (International ed. in English) · 2020
    Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

4 authors.

Jana M HolthoffFakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstraße 150, 44801, Bochum, Germany.
Elric EngelageFakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstraße 150, 44801, Bochum, Germany.ORCID http://orcid.org/0000-0003-4640-6260
Robert WeissInstitut für Organische Chemie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestraße 42, 91054, Erlangen, Germany.
Stefan M HuberFakultät für Chemie und Biochemie, Ruhr-Universität Bochum, Universitätsstraße 150, 44801, Bochum, Germany.ORCID http://orcid.org/0000-0002-4125-159X

Funding

Deutsche Forschungsgemeinschaft EXC 2033 - 390677874Studienstiftung des Deutschen Volkes
6 · The paper itself

Abstract

Halogen bonding is often described as being driven predominantly by electrostatics, and thus adducts between anionic halogen bond (XB) donors (halogen-based Lewis acids) and anions seem counterintuitive. Such "anti-electrostatic" XBs have been predicted theoretically but for organic XB donors, there are currently no experimental examples except for a few cases of self-association. Reported herein is the synthesis of two negatively charged organoiodine derivatives that form anti-electrostatic XBs with anions. Even though the electrostatic potential is universally negative across the surface of both compounds, DFT calculations indicate kinetic stabilization of their halide complexes in the gas phase and particularly in solution. Experimentally, self-association of the anionic XB donors was observed in solid-state structures, resulting in dimers, trimers, and infinite chains. In addition, co-crystals with halides were obtained, representing the first cases of halogen bonding between an organic anionic XB donor and a different anion. The bond lengths of all observed interactions are 14-21 % shorter than the sum of the van der Waals radii.

Indexed as

density-functional calculationselectrostaticshalogen bondinghydrogen bondingnoncovalent interactions

Identifiers

PMID32227661
PMCPMC7317790

What OpenQuestion holds

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Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.