2011
DOI: 10.1007/s11426-011-4412-x
|View full text |Cite
|
Sign up to set email alerts
|

Phenylboronic acids in crystal engineering: Utility of the energetically unfavorable syn,syn-conformation in co-crystal design

Abstract: Phenylboronic acids can exist, in principle, in three different conformers (syn,syn; syn,anti and anti,anti) with distinct energy profiles. In their native state, these compounds prefer the energetically favored syn,anti-conformation. In molecular complexes, however, the functionality exhibits conformational diversity. In this paper we report a series of co-crystals, with N-donor compounds, prepared by a design strategy involving the synthons based on the syn,syn-conformation of the boronic acid functionality… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1

Citation Types

0
40
0
1

Year Published

2012
2012
2023
2023

Publication Types

Select...
7

Relationship

1
6

Authors

Journals

citations
Cited by 40 publications
(41 citation statements)
references
References 35 publications
0
40
0
1
Order By: Relevance
“…[19][20][21][22] Isoreticular synthesis 23,24 and secondary building unit 25-27 approaches in metal−organic frameworks, and isostructurality [28][29][30] and modularity [31][32][33][34] in organic assemblies are a few thriving strategies in crystal engineering.…”
Section: Introductionmentioning
confidence: 99%
“…[19][20][21][22] Isoreticular synthesis 23,24 and secondary building unit 25-27 approaches in metal−organic frameworks, and isostructurality [28][29][30] and modularity [31][32][33][34] in organic assemblies are a few thriving strategies in crystal engineering.…”
Section: Introductionmentioning
confidence: 99%
“…[50][51][52] The outcome has been, admittedly, unexpected affording an entirely new class of adducts, which, for their zwitterionic nature may well prove useful in the construction of frameworks or supramolecular aggregates. From solution, slow cooling of the liquid leads predominantly to retrieve crystals of the "axle" compound while mechanochemical reaction between boronic acid and rhodizonic acid affords exclusively the tweezer-type compounds.…”
Section: Discussionmentioning
confidence: 99%
“…Gautam R. Desiraju and coworkers showed a design strategy for the preparation of co-crystals containing compounds in energetically unfavorable conformations. They used compounds with the 1,2-diazo fragment (such as alprazolam, 1H-tetrazole, acetazolamide and benzotriazole), 1,10-phenanthroline, and 2,2'-bipyridine for the co-crystallization studies ( Figure 6) [21]. Their work "shows that the mere presence of the 1,2-diazo fragment in the coformer does not guarantee the successful formation of co-crystals with a syn,syn-conformation of the boronic acid" [21].…”
Section: Analytical Inorganic and Solid-state Chemistrymentioning
confidence: 99%
“…Jianhua Cheng and Zhaomin Hou gave a short comment on rare-earth dialkyl and dihydride Figure 6 Graphic abstract of the paper by Desiraju et al [21].…”
Section: Analytical Inorganic and Solid-state Chemistrymentioning
confidence: 99%