Additions and Corrections: Concerted Displacement Reactions: The Reaction of Catechol with Acyl Halides.

Churchill, J. W.; Lapkin, M.; Martínez, Francisco Javier Martínez; Zaslowsky, J. A.

doi:10.1021/ja01557a638

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“…While in polyacrylamide the neighboring amide structures could form intramolecular hydrogen bonds that could decrease the electron density at the amide nitrogen and promote the chlorination. The higher chlorination rate of polyacrylamide can also be explained as a “concerted” polyfunctional mechanism . In hydrolysis of the primary amides, the higher initial hydrolysis rate of polyfunctional amide than monoamide was also caused by the acceleration effect from the neighboring amide group.…”

Section: Resultsmentioning

confidence: 99%

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New Refreshable N-Halamine Polymeric Biocides: N-Chlorination of Acyclic Amide Grafted Cellulose

Liu

Sun

2008

Ind. Eng. Chem. Res.

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Acyclic N-halamine structures have demonstrated antibacterial functions similar to cyclic N-halamine. Precursors of acyclic halamine such as acrylamide and methacrylamide can be easily grafted onto surfaces of substrates via radical polymerization processes. However, due to easy hydrolysis of primary amides during chlorination and steric hindrance of secondary amide to conversion to acyclic halamine structures, the acyclic halamines still have limitations to many applications in preparation of antimicrobial materials. To reduce hydrolysis of amide during chlorination, particularly under alkaline conditions, addition of electrolytes such as NaCl was able to improve chlorination of polyacrylamide grafted cotton (chlorine content 458 ppm) with less than 10% hydrolysis under slightly basic (pH = 8) conditions. Both acidic conditions and the addition of salt can increase the chlorination of secondary amides and provide effective antibacterial functions on the treated cellulose (5 log reduction of E. coli in contact time of 120 min).

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Section: Resultsmentioning

confidence: 99%

“…The higher chlorination rate of polyacrylamide can also be explained as a "concerted" polyfunctional mechanism. 12 In hydrolysis of the primary amides, the higher initial hydrolysis rate of polyfunctional amide than monoamide was also caused by the acceleration effect from the neighboring amide group.…”

Section: Resultsmentioning

confidence: 99%

New Refreshable N-Halamine Polymeric Biocides: N-Chlorination of Acyclic Amide Grafted Cellulose

Liu

Sun

2008

Ind. Eng. Chem. Res.

View full text Add to dashboard Cite

show abstract

Additions and Corrections: Concerted Displacement Reactions: The Reaction of Catechol with Acyl Halides.

Cited by 1 publication

References 0 publications

New Refreshable N-Halamine Polymeric Biocides: N-Chlorination of Acyclic Amide Grafted Cellulose

New Refreshable N-Halamine Polymeric Biocides: N-Chlorination of Acyclic Amide Grafted Cellulose

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