Peroxidation of C–H Bonds Adjacent to an Amide Nitrogen Atom under Mild Conditions

2014 ◽  
Vol 16 (12) ◽  
pp. 3204-3207 ◽  
Author(s):  
Hui Yu ◽  
Jie Shen
Keyword(s):  
Nitrogen Atom ◽  
Amide Nitrogen ◽  
Mild Conditions ◽  
Amide Nitrogen Atom

scholarly journals Unexpected Resistance to Base-Catalyzed Hydrolysis of Nitrogen Pyramidal Amides Based on the 7-Azabicyclic[2.2.1]heptane Scaffold

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2363 ◽  
Author(s):  
Diego Ocampo Gutiérrez de Velasco ◽  
Aoze Su ◽  
Luhan Zhai ◽  
Satowa Kinoshita ◽  
Yuko Otani ◽  
...  
Keyword(s):  
Nitrogen Atom ◽  
Amide Bond ◽  
Free Energies ◽  
Amide Nitrogen ◽  
Bond Rotation ◽  
Entropy Term ◽  
And Inversion ◽  
Kinetics Of ◽  
Hydrolysis Of ◽  
Amide Nitrogen Atom

Non-planar amides are usually transitional structures, that are involved in amide bond rotation and inversion of the nitrogen atom, but some ground-minimum non-planar amides have been reported. Non-planar amides are generally sensitive to water or other nucleophiles, so that the amide bond is readily cleaved. In this article, we examine the reactivity profile of the base-catalyzed hydrolysis of 7-azabicyclo[2.2.1]heptane amides, which show pyramidalization of the amide nitrogen atom, and we compare the kinetics of the base-catalyzed hydrolysis of the benzamides of 7-azabicyclo[2.2.1]heptane and related monocyclic compounds. Unexpectedly, non-planar amides based on the 7-azabicyclo[2.2.1]heptane scaffold were found to be resistant to base-catalyzed hydrolysis. The calculated Gibbs free energies were consistent with this experimental finding. The contribution of thermal corrections (entropy term, –TΔS‡) was large; the entropy term (ΔS‡) took a large negative value, indicating significant order in the transition structure, which includes solvating water molecules.

Influence of alkyl group on amide nitrogen atom on fluorescence quenching of tyrosine amide and N-acetyltyrosine amide

2004 ◽  
Vol 111 (2) ◽  
pp. 105-113 ◽  
Author(s):  
Justyna Mrozek ◽  
Alicja Rzeska ◽  
Katarzyna Guzow ◽  
Jerzy Karolczak ◽  
Wiesław Wiczk
Keyword(s):  
Nitrogen Atom ◽  
Fluorescence Quenching ◽  
Alkyl Group ◽  
Amide Nitrogen ◽  
Amide Nitrogen Atom

Micellar Catalysis of Organic Reactions. XVII. Hydrolysis of Nitrazepam and Some N-Alkylated Derivatives

1985 ◽  
Vol 38 (7) ◽  
pp. 1037 ◽  
Author(s):  
TJ Broxton ◽  
SR Morrison
Keyword(s):  
Aqueous Solution ◽  
Nitrogen Atom ◽  
Sodium Dodecyl Sulfate ◽  
Sodium Dodecyl ◽  
Initial Attack ◽  
Amide Nitrogen ◽  
High Acid ◽  
Alkyl Derivatives ◽  
Hydrolysis Of ◽  
Amide Nitrogen Atom

Product studies for the acid catalysed hydrolysis of nitrazepam and some N-alkyl derivatives in the presence of micelles of sodium dodecyl sulfate ( sds ) have been carried out by a U.V. spectrophotometric technique. Attack of water at C2 leading to initial amide cleavage is favoured by high acid concentrations, by micelles of sds and by small R groups attached to the amide nitrogen atom. For nitrazepam, a change of mechanism from water attack at C5 (leading to initial azomethine cleavage) to water attack at C2 (leading to initial amide cleavage) was observed on transfer from water to micelles of sds . For N-benzyl nitrazepam (1d), however, no change of mechanism was detected. Initial attack of water occurred at C5 (leading to initial azomethine cleavage), both in aqueous solution and in micelles of sds.

KI-catalyzed imidation of sp3 C–H bond adjacent to amide nitrogen atom

2012 ◽  
Vol 10 (39) ◽  
pp. 7869 ◽  
Author(s):  
Zhi-Qi Lao ◽  
Wen-He Zhong ◽  
Qing-Hua Lou ◽  
Zhong-Jun Li ◽  
Xiang-Bao Meng
Keyword(s):  
Nitrogen Atom ◽  
Amide Nitrogen ◽  
Amide Nitrogen Atom

Partition coefficients and ultraviolet absorption maxima for the cinnamoyl derivatives of some long-chain and large-ring amines

1970 ◽  
Vol 48 (8) ◽  
pp. 1340-1343 ◽  
Author(s):  
D. J. Currie ◽  
H. L. Holmes
Keyword(s):  
Nitrogen Atom ◽  
Chain Length ◽  
Partition Coefficients ◽  
The Other ◽  
Ring Size ◽  
Amide Nitrogen ◽  
Derivatives Of ◽  
Limiting Value ◽  
Long Chain ◽  
Amide Nitrogen Atom

Partition coefficients of the title compounds in the system cyclohexane–water do not increase steadily with increasing chain length or ring size but level off to a limiting value. Reasons are advanced to account for this observation. Absorption maxima, on the other hand, are not influenced by the size of the ring or the length of the chain but are dependent only upon the degree of substitution on the amide nitrogen atom.

scholarly journals Synthesis and optical properties of poly(p-benzamide)s bearing oligothiophene on the amide nitrogen atom through an alkylene spacer

2013 ◽  
Vol 45 (12) ◽  
pp. 1171-1176 ◽  
Author(s):  
Koji Takagi ◽  
Katsuya Nobuke ◽  
Yuma Nishikawa ◽  
Ryohei Yamakado
Keyword(s):  
Optical Properties ◽  
Nitrogen Atom ◽  
Amide Nitrogen ◽  
Amide Nitrogen Atom

scholarly journals Synthesis of New Bis(spiro-β-lactams) via Interaction of Methyl 1-Bromocycloalcanecarboxylates with Zinc and N,N′-Bis(arylmethylidene)benzidines

2019 ◽  
Vol 2019 ◽  
pp. 1-7 ◽  
Author(s):  
N. F. Kirillov ◽  
E. A. Nikiforova ◽  
D. V. Baibarodskikh ◽  
T. A. Zakharova ◽  
L. S. Govorushkin
Keyword(s):  
Nitrogen Atom ◽  
Carbonyl Group ◽  
Nucleophilic Addition ◽  
Ring Closure ◽  
Amide Nitrogen ◽  
Ester Carbonyl ◽  
Ester Carbonyl Group ◽  
Amide Nitrogen Atom

Interaction of the Reformatsky reagents, prepared from methyl 1-bromocyclopentane-1-carboxylate or methyl 1-bromocyclohexane-1-carboxylate, with N,N′-bis(arylmethylidene)benzidines has given rise to a set of intermediates as a result of nucleophilic addition to the C=N group of a substrate. Further intramolecular attack of the amide nitrogen atom onto the ester carbonyl group is responsible for the ring closure, which affords two series of spirocompounds: 2,2′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-2-azaspiro[3.4]octan-1-one) or 2,2′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-2-azaspiro[3.5]nonan-1-ones).

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