Intramolecular hydrogen bonds in crystals of thiophosphorylbenzopyrane derivatives – X-ray and FT-IR studies

Rybarczyk‐Pirek, Agnieszka J.; Dubis, Alina T.; Grabowski, Sławomir J.; Nawrot‐Modranka, Jolanta

doi:10.1016/j.chemphys.2005.07.019

Cited by 30 publications

(33 citation statements)

References 46 publications

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“…However, in the case of OxP_HNBeH model species electron density amounts to q HÁÁÁO = 0.0340 au and HÁÁÁO distance 1.862 Å in spite of BeHelectron donating properties. Similar trends were observed for the previously studied compounds [13,[46][47][48][49][50][51].…”

Section: Geometry Of the Hydrogen Bond And Topological Parameterssupporting

confidence: 87%

DFT studies and AIM analysis of intramolecular N–H···O hydrogen bonds in 3-aminomethylene-2 methoxy-5,6-dimethyl-2-oxo-2,3-dihydro-2λ5-[1,2]oxaphosphinin-4-one and its derivatives

Małecka

2009

Struct Chem

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The intramolecular N-HÁÁÁO hydrogen bonds in 3-aminomethylene-2 methoxy-5,6-dimethyl-2-oxo-2, 3-dihydro-2k 5 -[1,2]oxaphosphinin-4-one and its derivatives (F, H, Li, -BeH) were studied by DFT (density functional theory) methods. The results of calculations were obtained at B3LYP/6-311??G(d,p) level on model species, with the resonance-assisted hydrogen bonds (RAHB). Topological parameters such an electron density, its Laplacian, kinetic electron energy density, potential electron energy density, and total electron energy density at the bond critical points (BCP) of HÁÁÁO/N-H contact bonds from Bader's 'Atoms in molecules' (AIM) theory were analyzed in details. The energy of the N-HÁÁÁO interactions studied here was found rather weak (E HB = 2.53-12.08 kcal/mol). The results of AIM ellipticity indicated p-delocalization over all six atoms within ring.

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Section: Geometry Of the Hydrogen Bond And Topological Parameterssupporting

confidence: 87%

DFT studies and AIM analysis of intramolecular N–H···O hydrogen bonds in 3-aminomethylene-2 methoxy-5,6-dimethyl-2-oxo-2,3-dihydro-2λ5-[1,2]oxaphosphinin-4-one and its derivatives

Małecka

2009

Struct Chem

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“…In the case of p-nitro-and p-brominederivatives (IV and VI), the observed peaks of electron density maxima are fuzzy and shifted towards the N-oxide O1 oxygen atom. Similar pictures of Fourier difference maps in the area of intramolecular hydrogen bonding bridges are known for benzopyrane derivatives [37][38][39][40][41], and they have been treated as evidence of hydrogen bonding strengthening and possible dynamic proton transfer reaction.…”

Section: Intramolecular Hydrogen Bondsmentioning

confidence: 69%

Non-covalent interactions of N-phenyl-1,5-dimethyl-1H-imidazole-4-carboxamide 3-oxide derivatives—a case of intramolecular N-oxide hydrogen bonds

et al. 2017

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The crystal structures of new N-phenyl-1,5-dimethyl-1H-imidazole-4-carboxamide 3-oxide derivatives are reported. The results of X-ray diffraction showed the existence of intramolecular hydrogen bonding between carboxamide nitrogen donors and N-oxide oxygen acceptors. The use of Quantum Theory of Atoms in Molecules allowed its classification as a strong interaction, with energy about 10 kcal/mol, and of intermediate character between closed shell and shared bonds. Comparison of experimental data and quantum theoretical calculations indicated that a substituent attached to the phenyl ring in the para position influences the strength and geometry of the title hydrogen bonding. Stronger π-electronwithdrawing properties of the higher energy substituent of the intramolecular hydrogen bond are observed. Among other intermolecular contacts in the studied crystals are C-H…O/ C-H…N hydrogen bonds of imidazole carbon atoms and some π…π stacking interactions between aromatic molecular fragments. Their importance in stabilization of the crystal structure was confirmed by the results of Hirshfeld surface analysis.

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“…This stacking is accompanied by respective ring slippage equal to 1.481(4) Å and 1.546(4) Å. With regard to the structure of the 3-aminoflavone ligand, the differentiation of C-C bond lengths within the pyrane system is typical, [28][29][30][31][32] …”

Section: Crystal Structure Descriptionmentioning

confidence: 99%

“…28 Synthesis and characterization of trans-Pt(3-af ) 2 Cl 2 Synthesis of trans-Pt(3-af ) 2 Cl 2 . To the solution of 3-aminoflavone (3-af ) (0.273 g, 1 mmol) in dry ethyl acetate (200 ml) platinum chloride(II) (0.133 g, 0.5 mmol) was added.…”

Section: Synthesis Of 3-aminoflavone (3-af )mentioning

confidence: 99%

trans-Platinum(ii) complex of 3-aminoflavone – synthesis, X-ray crystal structure and biological activities in vitro

Fabijańska¹,

Studzian

Szmigiero

et al. 2015

Dalton Trans.

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Intramolecular hydrogen bonds in crystals of thiophosphorylbenzopyrane derivatives – X-ray and FT-IR studies

Cited by 30 publications

References 46 publications

DFT studies and AIM analysis of intramolecular N–H···O hydrogen bonds in 3-aminomethylene-2 methoxy-5,6-dimethyl-2-oxo-2,3-dihydro-2λ5-[1,2]oxaphosphinin-4-one and its derivatives

DFT studies and AIM analysis of intramolecular N–H···O hydrogen bonds in 3-aminomethylene-2 methoxy-5,6-dimethyl-2-oxo-2,3-dihydro-2λ5-[1,2]oxaphosphinin-4-one and its derivatives

Non-covalent interactions of N-phenyl-1,5-dimethyl-1H-imidazole-4-carboxamide 3-oxide derivatives—a case of intramolecular N-oxide hydrogen bonds

trans-Platinum(ii) complex of 3-aminoflavone – synthesis, X-ray crystal structure and biological activities in vitro

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