Protonation acidity constants for some benzamides, acetamides, and lactams
Protonation acidity constants for 27 benzamides, acetamides, and lactams have been determined. Ultraviolet, and 13 C and 1 H nmr, spectroscopic methods were used; almost all the spectra were found to be subject to medium effects, some quite severe, as the sulfuric acid concentration was increased. D...
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| Published in | Canadian journal of chemistry Vol. 59; no. 11; pp. 1568 - 1573 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Ottawa, Canada
NRC Research Press
01.06.1981
|
| Online Access | Get full text |
| ISSN | 0008-4042 1480-3291 |
| DOI | 10.1139/v81-231 |
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| Abstract | Protonation acidity constants for 27 benzamides, acetamides, and lactams have been determined. Ultraviolet, and
13
C and
1
H nmr, spectroscopic methods were used; almost all the spectra were found to be subject to medium effects, some quite severe, as the sulfuric acid concentration was increased. Despite this, the excess acidity (X-function) method gave accurate
and m* values. In all cases protonation, followed by a medium shift in the spectrum of the protonated form, was the only process taking place; protonation was essentially complete in 60% H
2
SO
4
. The results for the different bases are interpreted in terms of the resonance, inductive, and steric effects in operation in the acid and base forms. |
|---|---|
| AbstractList | Protonation acidity constants for 27 benzamides, acetamides, and lactams have been determined. Ultraviolet, and 13 C and 1 H nmr, spectroscopic methods were used; almost all the spectra were found to be subject to medium effects, some quite severe, as the sulfuric acid concentration was increased. Despite this, the excess acidity (X-function) method gave accurate [Formula: see text] and m* values. In all cases protonation, followed by a medium shift in the spectrum of the protonated form, was the only process taking place; protonation was essentially complete in 60% H 2 SO 4 . The results for the different bases are interpreted in terms of the resonance, inductive, and steric effects in operation in the acid and base forms. Protonation acidity constants for 27 benzamides, acetamides, and lactams have been determined. Ultraviolet, and 13 C and 1 H nmr, spectroscopic methods were used; almost all the spectra were found to be subject to medium effects, some quite severe, as the sulfuric acid concentration was increased. Despite this, the excess acidity (X-function) method gave accurate and m* values. In all cases protonation, followed by a medium shift in the spectrum of the protonated form, was the only process taking place; protonation was essentially complete in 60% H 2 SO 4 . The results for the different bases are interpreted in terms of the resonance, inductive, and steric effects in operation in the acid and base forms. |
| Abstract_FL | On a déterminé les constantes d'acidité de la protonation de 27 benzamides, acetamides et lactames. A cette fin on a utilisé la rmn du
1
H et du
I3
C ainsi que la spectroscopie ultraviolette; lorsque la concentration en acide sulfurique augmente, presque tous les spectres subissent des effets de milieu qui sont quelquefois très importants. En dépit de cette influence, la méthode d'excès d'acidité (fonction X) donne des valeurs précises de
et de m*. Dans tous les cas, la protonation, suivie d'un déplacement moyen dans le spectre de la forme protonée, est le seul processus qui a lieu; la protonation est tout à fait complète dans du H
2
SO
4
á 60%. On interprète les résultats des différentes bases en fonction de la résonance ainsi que des effets inductifs et stériques présents dans les formes acide et basique. [Traduit par le journal] |
| Author | Druet, Linda M Klausner, Adi E Yates, Keith Modro, Tomasz A Wan, Peter Cox, Robin A |
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| Snippet | Protonation acidity constants for 27 benzamides, acetamides, and lactams have been determined. Ultraviolet, and
13
C and
1
H nmr, spectroscopic methods were... Protonation acidity constants for 27 benzamides, acetamides, and lactams have been determined. Ultraviolet, and 13 C and 1 H nmr, spectroscopic methods were... |
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| Title | Protonation acidity constants for some benzamides, acetamides, and lactams |
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