Farewell to the HSAB Treatment of Ambident Reactivity
Publication type: Journal Article
Publication date: 2011-07-01
scimago Q1
wos Q1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
21726020
General Chemistry
Catalysis
Abstract
The concept of hard and soft acids and bases (HSAB) proved to be useful for rationalizing stability constants of metal complexes. Its application to organic reactions, particularly ambident reactivity, has led to exotic blossoms. By attempting to rationalize all the observed regioselectivities by favorable soft-soft and hard-hard as well as unfavorable hard-soft interactions, older treatments of ambident reactivity, which correctly differentiated between thermodynamic and kinetic control as well as between different coordination states of ionic substrates, have been replaced. By ignoring conflicting experimental results and even referring to untraceable experimental data, the HSAB treatment of ambident reactivity has gained undeserved popularity. In this Review we demonstrate that the HSAB as well as the related Klopman-Salem model do not even correctly predict the behavior of the prototypes of ambident nucleophiles and, therefore, are rather misleading instead of useful guides. An alternative treatment of ambident reactivity based on Marcus theory will be presented.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
5
10
15
20
25
30
|
|
|
Journal of Organic Chemistry
27 publications, 10.19%
|
|
|
Angewandte Chemie - International Edition
17 publications, 6.42%
|
|
|
Angewandte Chemie
16 publications, 6.04%
|
|
|
Chemistry - A European Journal
12 publications, 4.53%
|
|
|
Organic and Biomolecular Chemistry
11 publications, 4.15%
|
|
|
Organic Letters
10 publications, 3.77%
|
|
|
Chemical Science
9 publications, 3.4%
|
|
|
Tetrahedron
7 publications, 2.64%
|
|
|
Advanced Synthesis and Catalysis
6 publications, 2.26%
|
|
|
Journal of the American Chemical Society
6 publications, 2.26%
|
|
|
ACS Catalysis
5 publications, 1.89%
|
|
|
Physical Chemistry Chemical Physics
5 publications, 1.89%
|
|
|
Journal of Physical Chemistry C
4 publications, 1.51%
|
|
|
Synthesis
4 publications, 1.51%
|
|
|
Inorganica Chimica Acta
3 publications, 1.13%
|
|
|
Theoretical Chemistry Accounts
3 publications, 1.13%
|
|
|
European Journal of Organic Chemistry
3 publications, 1.13%
|
|
|
Asian Journal of Organic Chemistry
3 publications, 1.13%
|
|
|
Journal of Computational Chemistry
3 publications, 1.13%
|
|
|
Journal of Physical Chemistry A
3 publications, 1.13%
|
|
|
ACS Omega
3 publications, 1.13%
|
|
|
Chemical Communications
3 publications, 1.13%
|
|
|
Organic Chemistry Frontiers
3 publications, 1.13%
|
|
|
Nature Communications
2 publications, 0.75%
|
|
|
Coordination Chemistry Reviews
2 publications, 0.75%
|
|
|
European Journal of Medicinal Chemistry
2 publications, 0.75%
|
|
|
Chemical Reviews
2 publications, 0.75%
|
|
|
Organometallics
2 publications, 0.75%
|
|
|
Langmuir
2 publications, 0.75%
|
|
|
5
10
15
20
25
30
|
Publishers
|
10
20
30
40
50
60
70
80
90
|
|
|
Wiley
83 publications, 31.32%
|
|
|
American Chemical Society (ACS)
70 publications, 26.42%
|
|
|
Royal Society of Chemistry (RSC)
39 publications, 14.72%
|
|
|
Elsevier
38 publications, 14.34%
|
|
|
Springer Nature
13 publications, 4.91%
|
|
|
Georg Thieme Verlag KG
5 publications, 1.89%
|
|
|
Oxford University Press
2 publications, 0.75%
|
|
|
MDPI
2 publications, 0.75%
|
|
|
Taylor & Francis
2 publications, 0.75%
|
|
|
Walter de Gruyter
2 publications, 0.75%
|
|
|
Beilstein-Institut
1 publication, 0.38%
|
|
|
AIP Publishing
1 publication, 0.38%
|
|
|
The Electrochemical Society of Japan
1 publication, 0.38%
|
|
|
International Union of Crystallography (IUCr)
1 publication, 0.38%
|
|
|
The Society of Synthetic Organic Chemistry, Japan
1 publication, 0.38%
|
|
|
Institute of Electrical and Electronics Engineers (IEEE)
1 publication, 0.38%
|
|
|
OOO Zhurnal "Mendeleevskie Soobshcheniya"
1 publication, 0.38%
|
|
|
10
20
30
40
50
60
70
80
90
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
265
Total citations:
265
Citations from 2025:
12
(4.52%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Mayr H., Breugst M., Ofial A. R. Farewell to the HSAB Treatment of Ambident Reactivity // Angewandte Chemie - International Edition. 2011. Vol. 50. No. 29. pp. 6470-6505.
GOST all authors (up to 50)
Copy
Mayr H., Breugst M., Ofial A. R. Farewell to the HSAB Treatment of Ambident Reactivity // Angewandte Chemie - International Edition. 2011. Vol. 50. No. 29. pp. 6470-6505.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/anie.201007100
UR - https://doi.org/10.1002/anie.201007100
TI - Farewell to the HSAB Treatment of Ambident Reactivity
T2 - Angewandte Chemie - International Edition
AU - Mayr, Herbert
AU - Breugst, Martin
AU - Ofial, Armin R.
PY - 2011
DA - 2011/07/01
PB - Wiley
SP - 6470-6505
IS - 29
VL - 50
PMID - 21726020
SN - 1433-7851
SN - 1521-3773
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2011_Mayr,
author = {Herbert Mayr and Martin Breugst and Armin R. Ofial},
title = {Farewell to the HSAB Treatment of Ambident Reactivity},
journal = {Angewandte Chemie - International Edition},
year = {2011},
volume = {50},
publisher = {Wiley},
month = {jul},
url = {https://doi.org/10.1002/anie.201007100},
number = {29},
pages = {6470--6505},
doi = {10.1002/anie.201007100}
}
Cite this
MLA
Copy
Mayr, Herbert, et al. “Farewell to the HSAB Treatment of Ambident Reactivity.” Angewandte Chemie - International Edition, vol. 50, no. 29, Jul. 2011, pp. 6470-6505. https://doi.org/10.1002/anie.201007100.