Hydrogen-bond basicity of secondary and tertiary amides, carbamates, ureas and lactams

David Deniaud
Christian Laurence
Abdeljalil Lachkar
Maryvonne Helbert
Michel Berthelot
Publication typeJournal Article
Publication date1992-01-01
SJR
CiteScore
Impact factor
ISSN03009580, 13645471, 1472779X
General Environmental Science
General Earth and Planetary Sciences
Abstract
The hydrogen-bond basicity scale pKHB(logarithm of the formation constant of 4-fluorophenol–base complexes in CCl4) has been measured for tertiary and secondary amides, carbonates, ureas and lactams. The hydrogen-bonding fixation site is the carbonyl group, even for the very hindered amide ButCON(C6H11)2. In the amides R1CONR2R3 the hydrogen-bond basicity is decreased more by bulky R1 substituents on the carbonyl carbon than by bulky R2 and R3 substituents on nitrogen. The field effect of X substituents operates more effectively on hydrogen-bond basicity than the resonance effect in the XCONMe2 series. The hydrogen-bond basicity is increased by six-membered cyclisation.
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GOST Copy
Deniaud D. et al. Hydrogen-bond basicity of secondary and tertiary amides, carbamates, ureas and lactams // Journal of the Chemical Society Perkin Transactions 2. 1992. Vol. 12. p. 2091.
GOST all authors (up to 50) Copy
Deniaud D., Laurence C., Lachkar A., Helbert M., Berthelot M. Hydrogen-bond basicity of secondary and tertiary amides, carbamates, ureas and lactams // Journal of the Chemical Society Perkin Transactions 2. 1992. Vol. 12. p. 2091.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1039/p29920002091
UR - https://doi.org/10.1039/p29920002091
TI - Hydrogen-bond basicity of secondary and tertiary amides, carbamates, ureas and lactams
T2 - Journal of the Chemical Society Perkin Transactions 2
AU - Deniaud, David
AU - Laurence, Christian
AU - Lachkar, Abdeljalil
AU - Helbert, Maryvonne
AU - Berthelot, Michel
PY - 1992
DA - 1992/01/01
PB - Royal Society of Chemistry (RSC)
SP - 2091
IS - 12
SN - 0300-9580
SN - 1364-5471
SN - 1472-779X
ER -
BibTex
Cite this
BibTex (up to 50 authors) Copy
@article{1992_Deniaud,
author = {David Deniaud and Christian Laurence and Abdeljalil Lachkar and Maryvonne Helbert and Michel Berthelot},
title = {Hydrogen-bond basicity of secondary and tertiary amides, carbamates, ureas and lactams},
journal = {Journal of the Chemical Society Perkin Transactions 2},
year = {1992},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://doi.org/10.1039/p29920002091},
number = {12},
pages = {2091},
doi = {10.1039/p29920002091}
}