(1′R,3S)-2-Oxo-1-(1′-phenylethyl)piperidine-3-carboxylic acid: a case of a very strong intramolecular hydrogen bond

2004 ◽  
Vol 60 (11) ◽  
pp. o2110-o2112
Author(s):  
Ana-María Lumbreras-García ◽  
Alberto Galindo-Guzmán ◽  
Dino Gnecco ◽  
Joel-Luis Terán ◽  
Sylvain Bernès
Keyword(s):  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Intramolecular Hydrogen Bond ◽  
Intramolecular Hydrogen ◽  
Strong Intramolecular Hydrogen Bond

Aromatic amides. IX. Temperature effects on the N.M.R. spectra of substituted acetanilides

1974 ◽  
Vol 27 (12) ◽  
pp. 2617 ◽  
Author(s):  
ID Rae
Keyword(s):  
Hydrogen Bond ◽  
Chemical Shift ◽  
Benzene Ring ◽  
Intramolecular Hydrogen Bond ◽  
Temperature Effects ◽  
Dimethyl Sulphoxide ◽  
Intramolecular Hydrogen ◽  
Strong Intramolecular Hydrogen Bond ◽  
Ortho Substituent

N.m.r. spectra have been measured for several anilides in dimethyl sulphoxide solution for temperatures in the range 40-140�. The change of the N-H chemical shift with temperature depends on the nature of the ortho substituent on the benzene ring, being least when a strong intramolecular hydrogen bond is possible between the amide N-H and the ortho substituent. For 2?-nitroanilides, the 6?- proton becomes increasingly deshielded as the temperature is raised.

Temperature dependence of chemical shifts of protons in hydrogen bonds. Experimental evidence on an intramolecular hydrogen bond

1968 ◽  
Vol 46 (17) ◽  
pp. 2865-2868 ◽  
Author(s):  
T. Schaefer ◽  
G. Kotowycz
Keyword(s):  
Hydrogen Bond ◽  
Carbon Tetrachloride ◽  
Chemical Shift ◽  
Hydrogen Bonds ◽  
Temperature Dependence ◽  
Intramolecular Hydrogen Bond ◽  
Chemical Shifts ◽  
Hydroxyl Proton ◽  
Intramolecular Hydrogen ◽  
Strong Intramolecular Hydrogen Bond

A temperature dependence of the chemical shift of the hydroxyl proton in the strong intramolecular hydrogen bond in 3,5-dichlorosalicylaldehyde is observed in carbon tetrachloride and benzene-d6 solutions. Its magnitude of 0.25 to 0.30 × 10−2 p.p.m. per ° C over a range of 100 °C is in agreement with the model described by Muller and Reiter (1).

The synthesis of 5-hydroxy chromenes

1985 ◽  
Vol 63 (10) ◽  
pp. 2589-2596 ◽  
Author(s):  
J. W. ApSimon ◽  
L. W. Herman ◽  
C. Huber
Keyword(s):  
Hydrogen Bond ◽  
Oxygen Atom ◽  
Intramolecular Hydrogen Bond ◽  
Hydroxyl Group ◽  
X Ray ◽  
Type Reaction ◽  
Intramolecular Hydrogen ◽  
Strong Intramolecular Hydrogen Bond

The synthesis of 2,2-dimethyl-5-hydroxychromene (1d) is described. The synthesis of the analogous 5,7-dihydroxy derivatives, using similar conditions, yields the adduct 9 derived via a Bucherer type reaction. X-ray analysis of 9 demonstrated that a pyrrolidine group was in the 7-position, and that the 5-hydroxyl group was involved in a strong intramolecular hydrogen bond to the 4-keto oxygen atom.

Heterocyclic Tautomerism. The Solution and Crystal Structures of 1-(4',6'-Dimethylpyrimidin-2'-yl)-3-methylpyrazol-5-ol

1984 ◽  
Vol 37 (2) ◽  
pp. 459 ◽  
Author(s):  
PJ Steel ◽  
AR Whyte
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Crystal Structures ◽  
Intramolecular Hydrogen Bond ◽  
Title Compound ◽  
Intramolecular Hydrogen ◽  
Strong Intramolecular Hydrogen Bond

Both in the solid state and in solution, the title compound is shown to exist as the OH tautomer (3), which is stabilized by a strong intramolecular hydrogen bond. Crystals of the pyrazol-5-ol (3) are monoclinic: P 21/c, a 9.692(5), b 7.371(5), c 15.345(8) �, β 106.07(4)�, Z 4; the structure was refined to R 0.072 and Rw 0.062.

Femtosecond Mid-Infrared Pump–Probe Study of Wave Packet Motion in a Medium-Strong Intramolecular Hydrogen Bond

2002 ◽  
Vol 75 (5) ◽  
pp. 909-917 ◽  
Author(s):  
Dorte Madsen ◽  
Jens Stenger ◽  
Jens Dreyer ◽  
Peter Hamm ◽  
Erik T. J. Nibbering ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Wave Packet ◽  
Intramolecular Hydrogen Bond ◽  
Pump Probe ◽  
Mid Infrared ◽  
Intramolecular Hydrogen ◽  
Strong Intramolecular Hydrogen Bond

Pyramidal nitrogen inversion hindered by a strong intramolecular hydrogén bond in 2-diethylaminomethylphenols

1993 ◽  
Vol 31 (11) ◽  
pp. 1034-1037 ◽  
Author(s):  
G. S. Denisov ◽  
V. A. Gindin ◽  
N. S. Golubev ◽  
A. I. Koltsov ◽  
S. N. Smirnov ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Intramolecular Hydrogen Bond ◽  
Nitrogen Inversion ◽  
Intramolecular Hydrogen ◽  
Strong Intramolecular Hydrogen Bond ◽  
Pyramidal Nitrogen Inversion

Dielectric enrichment in binary solvent mixtures. The intramolecular hydrogen bond in N-alkyl-substituted o-nitroanilines. Substituent effects

1992 ◽  
Vol 70 (10) ◽  
pp. 2677-2682 ◽  
Author(s):  
Rosa Cattana ◽  
Juana J. Silber ◽  
Jorge Anunziata
Keyword(s):  
Hydrogen Bond ◽  
Intramolecular Hydrogen Bond ◽  
Preferential Solvation ◽  
Substituent Effects ◽  
Solvent Mixture ◽  
Binary Solvent ◽  
Solvent Mixtures ◽  
Hydrogen Bond Acceptor ◽  
Intramolecular Hydrogen ◽  
Strong Intramolecular Hydrogen Bond

In this work we report solvatochromism studies on o-nitroaniline and several N-alkyl-o-nitroaniline derivatives used as solutes in solvent mixtures of an "inert" nonpolar cosolvent, cyclohexane, and THF as a solvent with hydrogen bond acceptor ability. These studies allowed us to establish the competition between inter- and intramolecular hydrogen bond in solutes. This was done by comparing the magnitude of the local inhomogeneity induced by the solute-in-solvent mixture, that is, "preferential solvation," using Suppan's dielectric enrichment model as modified by us to be applied to electronic transitions. Since preferential solvation accounts for dielectric as well as specific interactions while dielectric enrichment only for the former, it was shown by comparison that it is possible to separate both effects and even quantify them. It was deduced that N-alkyl-o-nitroanilines form a strong intramolecular hydrogen bond, which remains unbroken even in polar solvents and hydrogen bond acceptors such as dimethyl sulfoxide. This was also confirmed by solvatochromic studies in pure solvents. On the other hand, a symmetrical dependence of the effects of alkyl substituents and solvents on the shifts of the absorption spectra was observed.

(E)-4-Bromo-2-(2-methoxyphenyliminomethyl)phenol

2007 ◽  
Vol 63 (11) ◽  
pp. o4241-o4241
Author(s):  
Zarife Sibel Gül ◽  
Ferda Erşahin ◽  
Erbil Ağar ◽  
Şamil Işık
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Dihedral Angle ◽  
Intramolecular Hydrogen Bond ◽  
Title Compound ◽  
Tautomeric Form ◽  
Aromatic Rings ◽  
Compound C ◽  
Intramolecular Hydrogen ◽  
Strong Intramolecular Hydrogen Bond

The molecule of the title compound, C14H12BrNO2, is almost planar and the dihedral angle between the planes of the two aromatic rings is 3.8 (2)°. The molecule exists in the crystal structure in the phenol–imine tautomeric form, with the H atom located on O rather than on N. This H atom is involved in a strong intramolecular hydrogen bond.

Three is company: dual intramolecular hydrogen-bond enabled carboxylic acid active in ring-opening polymerization

2016 ◽  
Vol 7 (5) ◽  
pp. 1111-1120 ◽  
Author(s):  
Jiaxi Xu ◽  
Jingjing Liu ◽  
Zhenjiang Li ◽  
Xiaopei Li ◽  
Cheng Chen ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Intramolecular Hydrogen Bond ◽  
Ring Opening ◽  
Active Catalyst ◽  
Ring Opening Polymerization ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Brönsted Acid ◽  
Intramolecular Hydrogen

Dual intramolecular H-bonding made weak Brønsted acid an active catalyst in cationic ring-opening polymerizations.

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