Recognition and applications of anion-anion dimers based on anti-electrostatic hydrogen bonds (AEHBs)

Chemical Society Reviews
Wei ZhaoNicholas White

Abstract

Based on Coulomb's Law alone, electrostatic repulsion between two anions is expected to prevent their dimerization. Contrary to that idea, this Tutorial Review will present evidence showing that anion-anion dimers of protic hydroxyanions can form readily, and describe conditions that facilitate their formation. From X-ray crystal structures, we learn that hydroxyanions dimerize and oligomerize by overcoming long-range electrostatic opposition. Common examples are hydroxyanions of phosphate, sulfate, and carbonate, often in partnership with charged and neutral receptors. Short-range hydrogen bonds between anionic donors and acceptors are defined as anti-electrostatic hydrogen bonds (AEHBs) with insight from theoretical studies. While anion dimers are difficult to identify unequivocally in solution, these solution dimers have recently been definitively identified. The development of the supramolecular chemistry of anion-anion dimers has led to applications in hierarchical assemblies, such as supramolecular polymers and hydrogen bonded organic frameworks.

References

Sep 1, 1969·The Journal of Physical Chemistry·C W Childs
Sep 22, 2005·Journal of the American Chemical Society·Steven R Kass
Apr 24, 2010·Nature Chemistry·Han-Yuan GongJonathan L Sessler
Jul 7, 2011·Chemistry : a European Journal·Giorgio BaggiLorenzo Mosca
Mar 13, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Ignasi MataEnrique Espinosa
Sep 10, 2014·Angewandte Chemie·Frank Weinhold, Roger A Klein
Oct 7, 2014·Chemistry : a European Journal·Nikola BregovićVladislav Tomišić
May 23, 2015·Chemical Reviews·Nathalie BusschaertPhilip A Gale
Mar 26, 2016·Journal of the American Chemical Society·Yun LiuAmar H Flood
May 27, 2016·Chemistry : a European Journal·Ibon AlkortaEnrique Espinosa
Oct 30, 2016·Angewandte Chemie·Elisabeth M FatilaAmar H Flood
Nov 3, 2016·Organic & Biomolecular Chemistry·Disha MungalparaStefan Kubik
May 12, 2017·Journal of the American Chemical Society·Qing HeJonathan L Sessler
Jun 2, 2017·Chemistry : a European Journal·Elisabeth M FatilaAmar H Flood
Sep 22, 2017·Chemical Communications : Chem Comm·J S McNallyA D Wilson
Jun 12, 2018·Journal of the American Chemical Society·Edward G SheetzAmar H Flood
Jan 25, 2019·Chemical Society Reviews·Rui-Biao LinBanglin Chen
Sep 19, 2019·Chemical Communications : Chem Comm·Duncan A CullenNicholas G White
Apr 1, 2020·Angewandte Chemie·Jana M HolthoffStefan M Huber

❮ Previous
Next ❯

Citations

Sep 15, 2020·Chemistry : a European Journal·Stephanie A BoerNicholas G White
Dec 30, 2020·Angewandte Chemie·Monika ChwastekAgnieszka Szumna
Feb 13, 2021·Chemistry, an Asian Journal·Émer M Foyle, Nicholas G White
Feb 16, 2021·Angewandte Chemie·Shanshan WangChuandong Jia
Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Patryk NiedbałaJanusz Jurczak
Jun 6, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Qingqing YangSteve Scheiner
Nov 12, 2020·Journal of the American Chemical Society·Hongye WangHao Li
Nov 13, 2020·Journal of the American Chemical Society·Thomas S C MacDonaldJonathon E Beves
Sep 21, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Andrea DaolioGiuseppe Resnati
Aug 20, 2021·Chemistry : a European Journal·Jana M HolthoffStefan M Huber
Oct 5, 2021·Chemical Communications : Chem Comm·Nicholas G White
Sep 16, 2021·Angewandte Chemie·Fangshun YangJonas Warneke
Sep 24, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Jorge DavidAlbeiro Restrepo

❮ Previous
Next ❯

Methods Mentioned

BETA
NMR
X-ray

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.