Proton Transfer Studies by Nuclear Magnetic Resonance. III. The Mean Life of the Amine-Water Hydrogen Bond in Aqueous Solution1a

1960 ◽  
Vol 82 (24) ◽  
pp. 6307-6314 ◽  
Author(s):  
Merle T. Emerson ◽  
Ernest Grunwald ◽  
Martin L. Kaplan ◽  
Robert A. Kromhout
1980 ◽  
Vol 58 (17) ◽  
pp. 1821-1828 ◽  
Author(s):  
Gary D. Fallon ◽  
Bryan M. Gatehouse ◽  
Allan Pring ◽  
Ian D. Rae ◽  
Josephine A. Weigold

Ethyl-3-amino-2-benzoyl-2-butenoate crystallizes from pentane as either the E (mp 82–84 °C) or the Z-isomer (mp 95.5–96.5 °C). The E isomer is less stable, and changes spontaneously into the Z, which bas been identified by X-ray crystallography. The structure is characterised by an N–H/ester CO hydrogen bond and a very long C2—C3 bond (1.39 Å). Nuclear magnetic resonance methods have been used to measure the rate of [Formula: see text] isomerization at several temperatures, leading to the estimate that the free energy of activation at 268 K is 56 ± 8 kJ.


1965 ◽  
Vol 6 (2) ◽  
pp. 111-117 ◽  
Author(s):  
Hazime Saitô ◽  
Kenkichi Nukada ◽  
Hiroshi Kato ◽  
Teijiro Yonezawa ◽  
Kenichi Fukui

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