Infrared spectra of phenols with intramolecular hydrogen bonds and their reactions with amines

1976 ◽  
Vol 25 (4) ◽  
pp. 1322-1324
Author(s):  
A. E. Lutskii ◽  
T. I. Klepanda ◽  
G. G. Sheina ◽  
L. P. Batrakova
1970 ◽  
Vol 23 (5) ◽  
pp. 947 ◽  
Author(s):  
LK Dyall

Measurements of N-H stretching frequencies of 4-nitroanilines in the presence of hydrogen bond acceptors show that the ease of forming a second intermolecular hydrogen bond in the presence of an ortho substituent decreases in the order hydrogen > methyl > bromo, methoxyl > nitro. This order demonstrates the importance of repulsions between lone pair orbitals on the ortho substituent and the acceptor molecule. Weak intramolecular hydrogen bonds are detected in 2-iodo- and 2-bromo-aniline, and such bonds can be strengthened by introduction of a 4-nitro substituent.


1963 ◽  
Vol 41 (9) ◽  
pp. 2240-2244 ◽  
Author(s):  
Henriette Bourassa-Bataille ◽  
P. Sauvageau ◽  
C. Sandorfy

The infrared spectra of the four ortho halophenols were measured in carbon tetrachloride solutions containing variable amounts of ether. The integrated intensities of the stretching band corresponding to the intermolecularly hydrogen-bonded OH groups were determined and plotted against ether concentration. From the curves obtained in this manner it was possible to deduce the relative strengths of the intramolecular hydrogen bonds which are present in these molecules. They are, in order of increasing strength: F < I < Br < Cl. This result is compared to others, published in the literature, obtained using alternative methods.


Author(s):  
Jacek Waluk ◽  
Arkadiusz Listkowski ◽  
Natalia Masiera ◽  
Michał Kijak ◽  
Roman Luboradzki ◽  
...  

1974 ◽  
Vol 20 (3) ◽  
pp. 414-415
Author(s):  
Ya. A. Shuster ◽  
V. A. Granzhan ◽  
P. M. Zaitsev

1991 ◽  
Vol 56 (4) ◽  
pp. 880-885 ◽  
Author(s):  
Oľga Hritzová ◽  
Dušan Koščík

Intramolecular hydrogen bonds of the N-H···O=C type have been detected in the derivatives of N-substituted N’-benzoyl- and N’-(2-chlorobenzoyl)thiourea on the basis of IR spectral studies. The title compounds can exist in two tautomeric forms.


1985 ◽  
Vol 25 (5) ◽  
pp. 808-810
Author(s):  
L. N. Kurkovskaya ◽  
Yu. M. Chunaev ◽  
N. M. Przhiyalgovskaya

2011 ◽  
Vol 89 (8) ◽  
pp. 971-977
Author(s):  
Danielle M. Chisholm ◽  
Robert McDonald ◽  
J. Scott McIndoe

Methylation of aromatic amino groups is usually straightforward, but the formation of two intramolecular hydrogen bonds in 3,3′-N,N′-bis(amino)-2,2′-bipyridine and (or) the potential for ring methylation prevents the clean tetramethylation of this molecule. Numerous attempts to make 3,3′-N,N′-bis(dimethylamino)-2,2′-bipyridine produced only complex mixtures of variously methylated products, and the only isolated molecule was 3,3′-N,N′-bis(methylamino)-2,2′-bipyridine, for which an X-ray crystal structure was obtained.


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