The Structure of 2‐[(1S)‐(+)‐10‐camphorsulfonamino]‐6‐aminopyridine in the Solid State and in Solution; Unprecedented Cocrystallization of Four Stereoisomers

Chen, Tsun‐Ren; Wu, Ying‐Yann; Chen, Jhy‐Der; Keng, Tai‐Chiun; Wang, Ju‐Chun

doi:10.1002/jccs.200300123

Cited by 4 publications

(2 citation statements)

References 23 publications

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“…Desiraju and co-workers have previously discussed the difference in hydrogen bond strengths between forms I and II , and synthesized and crystallized a set of phenylsubstituted analogues of VI , but in all their cases, which cover both forms I and II, the proton was observed at the pyridine nitrogen, i.e., a sulfonimide. In contrast, Chen and co-workers synthesized another analogue of VI , and here the observed structure is a sulfonamide . Of particular interest is also sulfapyridine, a closely related compound, which features a crystal structure with both the imide and amide tautomers present .…”

Section: Introductionmentioning

confidence: 78%

“…In contrast, Chen and coworkers synthesized another analogue of VI, and here the observed structure is a sulfonamide. 17 Of particular interest is also sulfapyridine, a closely related compound, which features a crystal structure with both the imide and amide tautomers present. 18 Moreover, Henry reported on a 25:75 distribution for the sulfonimide/sulfonamide crystal structures available in the literature.…”

Section: ■ Introductionmentioning

confidence: 99%

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Molecule VI: Sulfonimide or Sulfonamide?

Lill

Broo

2014

Crystal Growth & Design

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The tautomerism of molecule VI, a benchmark system for crystal structure predictions, has been investigated by the use of computational chemistry. Ab initio and density functional calculations including dispersion corrections show that monomers of molecule VI strongly (11 kcal mol −1 ) prefer to exist as sulfonamide tautomer, while remarkably the equilibrium is shifted toward sulfonimide tautomers in larger aggregates due to formation of stronger hydrogen bonds for the imide tautomer.

show abstract

Section: Introductionmentioning

confidence: 78%

Section: ■ Introductionmentioning

confidence: 99%

Molecule VI: Sulfonimide or Sulfonamide?

Lill

Broo

2014

Crystal Growth & Design

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Supramolecular Control over Tautomerism in Organic Solids

2016

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The Structure of Bis[N‐6‐aminopyridyl‐N‐(1S)‐(+)‐10‐camphorsulfonylamino]palladium in the Solid State and in Solution

Chen

et al. 2004

J Chinese Chemical Soc

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The complex, bis[N-6-aminopyridyl-N-(1S)-(+)-10-camphorsulfonylamino]palladium, Pd[(S)-APCS]2, 1, was prepared by reaction of 2-[(1S)-(+)-10-camphorsulfonamino]-6-aminopyridine with PdCl2 in THF. Complex 1 has been characterized by spectroscopic methods and its structure has been determined by X-ray crystallography. Crystal data: space group C2, a = 16.082 (2), b = 17.104 (2), c = 13.051 (2) Å, b = 99.95 (1)°, V = 3535.9 (8) Å 3 , Z = 2 with final residuals R1 = 0.0491 and wR2 = 0.0944. Two independent molecules, (S,S)-Pd[(S)-APCS]2, 1a, and (R,R)-Pd[(S)-APCS]2, 1b, were found in each asymmetric unit, which exchange to each other via a series of nitrogen inversion and C-C bond rotation. The inversion energy (DGc 1 ¹ ) and the energy barrier (DGc2 ¹ ) were 11.5 ± 0.1 Kcal mol -1 at 246 K and 9.8 ± 0.1 Kcal mol -1 at 199 K, respectively, calculated by dynamic NMR data.

show abstract

The Structure of 2‐[(1S)‐(+)‐10‐camphorsulfonamino]‐6‐aminopyridine in the Solid State and in Solution; Unprecedented Cocrystallization of Four Stereoisomers

Cited by 4 publications

References 23 publications

Molecule VI: Sulfonimide or Sulfonamide?

Molecule VI: Sulfonimide or Sulfonamide?

Supramolecular Control over Tautomerism in Organic Solids

The Structure of Bis[N‐6‐aminopyridyl‐N‐(1S)‐(+)‐10‐camphorsulfonylamino]palladium in the Solid State and in Solution

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