NUCLEAR MAGNETIC RESONANCE STUDIES OF THE PROTONATION OF WEAK BASES IN FLUOROSULPHURIC ACID: IV. PHENOLS AND AROMATIC ETHERS

1964 ◽  
Vol 42 (6) ◽  
pp. 1433-1439 ◽  
Author(s):  
T. Birchall ◽  
A. N. Bourns ◽  
R. J. Gillespie ◽  
P. J. Smith
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Perchloric Acid ◽  
Ultraviolet Spectroscopy ◽  
Aromatic Carbon ◽  
Magnetic Resonance Studies ◽  
Weak Bases ◽  
Nuclear Magnetic

The n.m.r. spectra of phenol, anisole, and other phenols and aromatic ethers in solution in fluorosulphuric acid and in 70% perchloric acid show that in every case they protonate on an aromatic carbon. Earlier evidence from ultraviolet spectroscopy that phenol and anisole protonate on oxygen is reinterpreted.

NUCLEAR MAGNETIC RESONANCE STUDIES OF THE PROTONATION OF WEAK BASES IN FLUOROSULFURIC ACID: V. KETONES, CARBOXYLIC ACIDS, AND SOME OTHER OXYGEN BASES

1965 ◽  
Vol 43 (5) ◽  
pp. 1045-1051 ◽  
Author(s):  
T. Birchall ◽  
R. J. Gillespie
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Chemical Shift ◽  
Ethyl Acetate ◽  
Carboxylic Acids ◽  
Ethyl Alcohol ◽  
Magnetic Resonance Studies ◽  
Weak Bases ◽  
Nuclear Magnetic ◽  
Proton Loss

The proton n.m.r. spectra of the conjugate acids of some ketones and carboxylic acids, and of ethyl acetate, nitromesitylene, and ethyl alcohol have been observed. A correlation has been found between the chemical shift of the C=OH+ proton of the conjugate acids of some para-substituted acetophenones and their pKBH + and σ+ values. The rates of proton loss from these conjugate acids have been obtained.

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