Photoelectron-determined core binding energies and predicted gas-phase basicities for the 2-hydroxypyridine .dblarw. 2-pyridone system

Brown, R. S.; Tse, A.; Vederas, John C.

doi:10.1021/ja00523a050

Cited by 95 publications

(58 citation statements)

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“…31 In gas phase studies, it has been reported that 2HP is more stable than 2PY by ϳ270 cm Ϫ1 , and the tautomerization barrier is ϳ16 000 cm Ϫ1 . [1][2][3][4][5][6][7][15][16][17][18][19][20][21] In liquid phases, both forms coexist in nonpolar solvents, while 2PY substantially dominates in a pure crystalline or in polar solvents. 1,3,11,12,19 Such a difference of the relative abundance in solvents can be associated with the relative stabilization energy and a drastic decrease of the barrier height by the solvation.…”

Section: Introductionmentioning

confidence: 99%

Vibrational spectroscopy of 2-pyridone and its clusters in supersonic jets: Structures of the clusters as revealed by characteristic shifts of the NH and C=O bands

Matsuda¹,

Ebata²,

Mikami³

1999

The Journal of Chemical Physics

153

159

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Articles you may be interested inPhotofragment emission yield spectroscopy of acetylene in the D̃ 1 Π u , Ẽ 1 A, and F̃ 1 Σ u + states by vacuum ultraviolet and infrared vacuum ultraviolet double-resonance laser excitations Structures of hydrogen-bonded clusters of benzyl alcohol with water investigated by infrared-ultraviolet double resonance spectroscopy in supersonic jet J. Chem. Phys. 111, 8438 (1999); 10.1063/1.480184 Structures and the vibrational relaxations of size-selected benzonitrile-( H 2 O ) n=1-3 and -( CH 3 OH ) n=1-3 clusters studied by fluorescence detected Raman and infrared spectroscopies J. Chem. Phys. 110, 9504 (1999); 10.1063/1.478915Characterizations of the hydrogen-bond structures of 2-naphthol-( H 2 O ) n (n=0-3 and 5) clusters by infraredultraviolet double-resonance spectroscopy Vibrational spectroscopy of the key functional vibrations of 2-pyridone and its hydrogen-bonded clusters with water, methanol, dioxane, dimethylether, as well as its dimer, has been carried out by using infrared-ultraviolet ͑IR-UV͒ and stimulated Raman-UV double resonance methods combined with fluorescence detection. The characteristic spectral changes upon the cluster formation have been observed for the NH and CvO stretching vibrations of the bare molecule and also for the OH stretching vibrations of the solvent molecules. The cluster structures were investigated by comparing the observed spectra with the simulated ones of the energy-optimized structures obtained by ab-initio molecular orbital calculations. It was found that the ''ring-type'' hydrogen-bonded structure is appropriate for the cluster with water or methanol, while the ''linear-type'' hydrogen-bonded structure is appropriate for the cluster with dioxane or dimethylether. The symmetric form of 2-pyridone dimer was confirmed by the observed spectra, as well as the ab-initio calculation. A clear correlation between the observed frequency shifts of the NH stretching vibrations and the calculated NH¯O hydrogen-bond angles was obtained indicating that the hydrogen-bond angle distortion reduces the local hydrogen-bond strength. Also it was found the blue shifts of the origin bands of the S 1 ←S 0 electronic transition strongly depends on the type of the cluster structures.

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Section: Introductionmentioning

confidence: 99%

Vibrational spectroscopy of 2-pyridone and its clusters in supersonic jets: Structures of the clusters as revealed by characteristic shifts of the NH and C=O bands

Matsuda¹,

Ebata²,

Mikami³

1999

The Journal of Chemical Physics

153

159

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“…1,2 A variety of experimental measurements [3][4][5][6][7] has indicated that the free energy difference between the 2HP and the 2PY forms is 2-4 kJ/mol in favor of the hydroxy form. Most of the theoretical methods [8][9][10][11][12] used so far have supported this result.…”

Section: Introductionmentioning

confidence: 99%

“…(2) to determine the structures of the 2HP-NH 3 and 2HP-(NH 3 ) 2 complexes and to compare these with the structures of the 2PY-NH 3 and 2PY-(NH 3 ) 2 complexes, (3) to determine the stability difference between 2PY and 2HP complexed with one and two ammonia molecules, (4) to compare the structural parameters and the rotational constants for the 2PY-NH 3 and 2PY-(NH 3 ) 2 complexes with corresponding experimental data as well as with MP2 results, and (5) to study the cooperative effect in the heterotrimer systems.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Investigation of the Interaction between 2-Pyridone/2-Hydroxypyridine and Ammonia

2000

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The structures and harmonic vibrational frequencies of the closed complexes 2-pyridone-NH 3 (2PY-NH 3 ), 2-hydroxypyridine-NH 3 (2HP-NH 3 ), 2-pyridone-(NH 3 ) 2 (2PY-(NH 3 ) 2 ), and 2-hydroxypyridine-(NH 3 ) 2 (2HP-(NH 3 ) 2 ) were studied using the density functional theory (DFT). The final energies of each complex were obtained using the B3-LYP and MP2 methods. The NH 3 molecule is both a proton donor and a proton acceptor in the 2PY-NH 3 and 2HP-NH 3 complexes, while in the 2PY-(NH 3 ) 2 and 2HP-(NH 3 ) 2 systems, the ammonia dimer acts both as a proton donor and a proton acceptor. Comparison is made between the theoretical results and recent experimental results for the 2PY-NH 3 and 2PY-(NH 3 ) 2 complexes. In the heterotrimer complexes, the cooperative effects are substantial and this is reflected by the intermolecular distance of the ammonia dimer, by the elongation of the NH bond length, by the frequency shift of the ν(NH) mode, and by the additive interaction energy.

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“…For the structural description, different canonical forms, 1 -2 of the lactam (1) or 3 -4 of the lactim (3) tautomers can be written (2)(3)(4)(5)(6).…”

Section: Introductionmentioning

confidence: 99%

Structural studies of organoboron compounds. XVIII. Crystal and molecular structures of 2,2-diphenyl-1,3-dioxa-3a-azonia-2-borataindan and 4-cyclohexyl-6-methyl-2,2-diphenyl-1,3-dioxa-3a-azonia-2-borataindan

Kliegel¹,

Nanninga²,

Rettig³

et al. 1983

Can. J. Chem.

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. 61, 2493 (1983). The crystal structures of 2,2-d1phenyl-l,3-dioxa-3a-azonia-2-borataindan, 6a, and 4-cyclohexyl-6-methyl-2,2-d~phenyl-1,3-dioxa-3a-azonia-2-borataindan, 6b, reported here represent the first crystallographic examples of coordination complexes of the anionic ligand derivedo from 2-hydroxypyridine N-oxide. Crystals of 6a are monoclinic, a = 11.5210(13), 6 = 10.2860(8), c = 12.7354(15) A, P = olO1 .878(5)", Z = 4, space group P 2 , l c ; and those of 6b are monoclin~c, a = 8.5047 (8)

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Photoelectron-determined core binding energies and predicted gas-phase basicities for the 2-hydroxypyridine .dblarw. 2-pyridone system

Cited by 95 publications

References 1 publication

Vibrational spectroscopy of 2-pyridone and its clusters in supersonic jets: Structures of the clusters as revealed by characteristic shifts of the NH and C=O bands

Vibrational spectroscopy of 2-pyridone and its clusters in supersonic jets: Structures of the clusters as revealed by characteristic shifts of the NH and C=O bands

Theoretical Investigation of the Interaction between 2-Pyridone/2-Hydroxypyridine and Ammonia

Structural studies of organoboron compounds. XVIII. Crystal and molecular structures of 2,2-diphenyl-1,3-dioxa-3a-azonia-2-borataindan and 4-cyclohexyl-6-methyl-2,2-diphenyl-1,3-dioxa-3a-azonia-2-borataindan

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