Hydrogen-bonded nucleophile effects in ANS: the reactions of 1-chloro and 1-fluoro-2,4-dinitrobenzene with 2-guanidinobenzimidazole, 1-(2-aminoethyl)piperidine and N -(3-aminopropyl)morpholine in aprotic solvents

2011 ◽  
Vol 24 (2) ◽  
pp. 101-109 ◽  
Author(s):  
Cecilia E. Silvana Alvaro ◽  
Alicia D. Ayala ◽  
Norma S. Nudelman
Keyword(s):  
Aprotic Solvents ◽  
Hydrogen Bonded

Tropolone-triethylamine equilibria in various solvents

1980 ◽  
Vol 33 (3) ◽  
pp. 491 ◽  
Author(s):  
B Poh ◽  
H Siow
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Dielectric Constant ◽  
Aprotic Solvent ◽  
Ion Pair ◽  
Pair Formation ◽  
Spectroscopic Methods ◽  
Aprotic Solvents ◽  
Ion Pair Formation ◽  
No Formation ◽  
Hydrogen Bonded

Infrared and nuclear magnetic resonance spectroscopic methods were used to study the tropolonetriethylamine equilibria. In aprotic solvents tropolone transfers its proton to triethylamine to form an ion pair which is in equilibrium with the intramolecularly hydrogen-bonded tropolone. The extent of ion pair formation increases with the dielectric constant of the aprotic solvent. Unlike the case of the p- nitrophenol-triethylamine system, there is no formation of a hydrogen bonded complex between tropolone and triethylamine. In the case of the tropolone-dibutylamine system in aprotic solvents, only ion pair formation is observed.

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