Hydrogen bond induced twisted intramolecular charge transfer in 2-(4′-N,N-dimethylaminophenyl)imidazo[4,5-b]pyridine

Dash, Nihar; Chipem, Francis A. S.; Swaminathan, Rajaram; Krishnamoorthy, G.

doi:10.1016/j.cplett.2008.05.092

Cited by 60 publications

(107 citation statements)

References 37 publications

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“…This may be due to greater stabilization of the TICT state by H-bonding with the acceptor, which should increase the activation energy barrier for the reverse process. Like DMAPPI, 2-(4 0 -N,N-dimethylaminophenyl)imidazo [4,5-b]pyridine (DMAPIP-b) (Figure 14.15) also shows longer-wavelength emission only in protic solvents [83]. The ratio of normal emission to TICT emission increases with increasing H-donating capacity of the solvent.…”

Section: Hydrogen Bonding With the Acceptor Moietymentioning

confidence: 99%

“…This was further substantiated by ab initio calculations showing that the electron density on (Table 14.3). The ab initio calculation performed predicted that both in DMAPPI and DMAPIP-b the donor (dimethylamino group), the phenyl ring and the acceptor (pyridoimidazole moiety) are coplanar in the ground state [83]. DFT calculations performed later for DMAPIP-b also predicted that the phenyl ring and the pyridoimidazole moiety are in same molecular plane [85].…”

Section: Hydrogen Bonding With the Acceptor Moietymentioning

confidence: 99%

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Hydrogen‐Bonding Effects on Intramolecular Charge Transfer

Krishnamoorthy

2010

Hydrogen Bonding and Transfer in the Excited State

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Section: Hydrogen Bonding With the Acceptor Moietymentioning

confidence: 99%

Section: Hydrogen Bonding With the Acceptor Moietymentioning

confidence: 99%

Hydrogen‐Bonding Effects on Intramolecular Charge Transfer

Krishnamoorthy

2010

Hydrogen Bonding and Transfer in the Excited State

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“…For example, they are known for their anticancer activity (Dash et al, 2008) and antibacterial (Capelli et al, 2006), antimitotic (Temple, 1990) and tuberculostatic (Bukowski & Janowiec, 1989) properties. In a previous study, we reported the synthesis of ethyl 2-(6-bromo-2-phenyl-1H-imidazo [4,5-b]-pyridin-1-yl)acetate (Hjouji et al, 2016).…”

Section: Structure Descriptionmentioning

confidence: 99%

Ethyl 2-(6-bromo-2-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)acetate

Hjouji¹,

Mague

Rodi³

et al. 2016

IUCr Data

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The title imidazo [4,5-b] pyridine derivative, C 16 H 14 BrN 3 O 2 , crystallizes with two independent molecules (1 and 2) in the asymmetric unit. In molecule 1, the pendant phenyl ring is inclined to the imidazo [4,5-b]pyridine core by 43.10 (4) while in molecule 2 the corresponding angle is 49.43 (4) . The two molecules differ primarily in the conformations of the ester substituents. In the crystal, molecules are linked via C-HÁ Á ÁN and C-HÁ Á ÁO hydrogen bonds, forming sheets parallel to the ab plane. Structure descriptionImidazo [4,5-b]pyridines are an important class of heterocyclic rings, considered as analogue of purine, widely studied owing to their broad biological activities. For example, they are known for their anticancer activity (Dash et al., 2008) and antibacterial (Capelli et al., 2006), antimitotic (Temple, 1990) and tuberculostatic (Bukowski & Janowiec, 1989) properties. In a previous study, we reported the synthesis of ethyl 2-(6-bromo-2-phenyl-1H-imidazo[4,5-b]-pyridin-1-yl)acetate (Hjouji et al., 2016). The present study is extended to the synthesis of the ethyl 2-(6-bromo-2-phenyl-3H-imidazo [4,5-b]pyridin-3-yl)acetate regioisomer, by the action of ethyl 2-bromoacetate on 6-bromo-2-phenyl-3H-imidazo [4,5-b]pyridine under the same conditions.The asymmetric unit of the title compound, contains two independent molecules (1 and 2), which differ primarily in the conformations of the ester substituents ( Figs. 1 and 2). The bicyclic imidazo [4,5-b]pyridine core of molecule 1 is planar to within 0.012 (1) Å , while that in molecule 2 is planar to within 0.020 (1) Å . In molecule 1, the pendant phenyl

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“…Indeed, the involvement of such a covalent character has been well appreciated in various types of HB. 35 The relative suitabilities of the Morse and LJ 12-10 functions for the radial part of HB potential can be further assessed by comparing their calculated energy values with those of the knowledge-based HB potential derived from the statistical analysis of the protein dataset for PPI. Figure 5 compares the energy values calculated with the two potential functions and with PDB statistics for the same set of R, h, and / values.…”

mentioning

confidence: 99%

New angle‐dependent potential energy function for backbone–backbone hydrogen bond in protein–protein interactions

Choi¹,

Kang²,

Park³

2009

J Comput Chem

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Backbone-backbone hydrogen bonds (BBHBs) are one of the most abundant interactions at the interface of protein-protein complex. Here, we propose an angle-dependent potential energy function for BBHB based on density functional theory (DFT) calculations and the operation of a genetic algorithm to find the optimal parameters in the potential energy function. The angular part of the energy function is assumed to be the product of the power series of sine and cosine functions with respect to the two angles associated with BBHB. Two radial functions are taken into account in this study: Morse and Leonard-Jones 12-10 potential functions. Of these two functions under consideration, the former is found to be more accurate than the latter in terms of predicting the binding energies obtained from DFT calculations. The new HB potential function also compares well with the knowledge-based potential derived by applying Boltzmann statistics for a variety of protein-protein complexes in protein data bank.

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Hydrogen bond induced twisted intramolecular charge transfer in 2-(4′-N,N-dimethylaminophenyl)imidazo[4,5-b]pyridine

Cited by 60 publications

References 37 publications

Hydrogen‐Bonding Effects on Intramolecular Charge Transfer

Hydrogen‐Bonding Effects on Intramolecular Charge Transfer

Ethyl 2-(6-bromo-2-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)acetate

New angle‐dependent potential energy function for backbone–backbone hydrogen bond in protein–protein interactions

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