Study of imidazo[1,2-a]pyridin-8-ol. 2. Crystal structure

Rydzkowski, R.; Blondeau, D.; Cazé, C.; Barbier, P.

doi:10.1107/s0108270187006620

Cited by 6 publications

(8 citation statements)

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“…1). All bond lengths and angles in both molecules are within normal ranges (Table 1) and are comparable to those in published structures (Rydzkowski et al, 1988;Zhang & Hu, 2005).…”

Section: Commentsupporting

confidence: 84%

2-(3-Bromo-4-methoxyphenyl)imidazo[1,2-a]pyridine

Duan

Sun

et al. 2006

Acta Cryst E

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“…1). All bond lengths and angles in both molecules are within normal ranges (Table 1) and are comparable to those in published structures (Rydzkowski et al, 1988;Zhang & Hu, 2005).…”

Section: Commentsupporting

confidence: 84%

2-(3-Bromo-4-methoxyphenyl)imidazo[1,2-a]pyridine

Duan

Sun

et al. 2006

Acta Cryst E

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“…Upon increasing the excitation wavelength up to 320 nm the maximum of the fluorescence spectrum shifts to the red side. Earlier Cazé and co-workers reported the absorption spectra of HIP in water at different pH values and our results agree with their findings 13b…”

Section: Introductionsupporting

confidence: 93%

“…This interaction breaks the intramolecular hydrogen bond formed in the isolated HIP molecule. Formation of intermolecular H-bonds between HIP and water has been experimentally observed 13a. In addition to this, the preference of HIP to establish intermolecular H-bonds accords with the crystal structure of HIP, where the OH group of the six-membered ring of the enol tautomer is engaged in an intermolecular H-bond with the N atom of another HIP molecule …”

Section: Resultsmentioning

confidence: 65%

“…Formation of intermolecular H-bonds between HIP and water has been experimentally observed 13a. In addition to this, the preference of HIP to establish intermolecular H-bonds accords with the crystal structure of HIP, where the OH group of the six-membered ring of the enol tautomer is engaged in an intermolecular H-bond with the N atom of another HIP molecule 5 Geometries of the stationary points for the proton-transfer process in the S 0 state of the HIP:H 2 O complex.…”

Section: Resultsmentioning

confidence: 98%

“…Recently we have carried out a detailed absorption and emission study of HIP in different (polar and apolar) media. A complete report of the results will be given elsewhere 13a. Here we outline the points directly related to the present work.…”

Section: Introductionmentioning

confidence: 84%

See 2 more Smart Citations

Proton-Transfer Reaction in Isolated and Water-Complexed 8-Hydroxyimidazo[1,2-a]Pyridine in the S₀ and S₁ Electronic States. A Theoretical Study

et al. 1999

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The intramolecular proton-transfer reaction of 8-hydroxyimidazo[1,2-a]pyridine (HIP) is studied in both the ground (S 0 ) and first singlet excited (S 1 ) electronic states. Ab initio calculations at the HF/MP2 and CIS/MP2 levels, respectively for S 0 and S 1 , reveal the existence of two tautomers. In gas phase the enol (E) form is the more stable one in S 0 , whereas in S 1 the zwitterionic (Z) tautomer becomes the lowest in energy. The energy barrier for the proton-transfer process is quite high in both electronic states. Introduction of one water molecule in the system greatly changes the picture of the whole process. A 1:1 complex involving two hydrogen bonds between HIP and water is formed. The H-bond bridge greatly facilitates the proton transfer in both S 0 and S 1 states. Additionally, for the two considered electronic states the Z structure is more stabilized than the E one. The trends of lowering the energy barrier and stabilizing the Z structure with respect to E are more prominent when the bulk effect of the solvent is introduced through a continuum (i.e. cavity) model. The energy profiles obtained for both S 0 and S 1 allow prediction of the electronic spectra of HIP in different media.

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Bicyclic 5-6 Systems with One Ring Junction Nitrogen Atom: One Extra Heteroatom 1:0

Howard

1996

Comprehensive Heterocyclic Chemistry II

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Study of imidazo[1,2-a]pyridin-8-ol. 2. Crystal structure

Cited by 6 publications

References 1 publication

2-(3-Bromo-4-methoxyphenyl)imidazo[1,2-a]pyridine

2-(3-Bromo-4-methoxyphenyl)imidazo[1,2-a]pyridine

Proton-Transfer Reaction in Isolated and Water-Complexed 8-Hydroxyimidazo[1,2-a]Pyridine in the S₀ and S₁ Electronic States. A Theoretical Study

Bicyclic 5-6 Systems with One Ring Junction Nitrogen Atom: One Extra Heteroatom 1:0

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Study of imidazo[1,2-a]pyridin-8-ol. 2. Crystal structure

Cited by 6 publications

References 1 publication

2-(3-Bromo-4-methoxyphenyl)imidazo[1,2-a]pyridine

2-(3-Bromo-4-methoxyphenyl)imidazo[1,2-a]pyridine

Proton-Transfer Reaction in Isolated and Water-Complexed 8-Hydroxyimidazo[1,2-a]Pyridine in the S0 and S1 Electronic States. A Theoretical Study

Bicyclic 5-6 Systems with One Ring Junction Nitrogen Atom: One Extra Heteroatom 1:0

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Proton-Transfer Reaction in Isolated and Water-Complexed 8-Hydroxyimidazo[1,2-a]Pyridine in the S₀ and S₁ Electronic States. A Theoretical Study