Matches in SemOpenAlex for { <https://semopenalex.org/work/W2023161791> ?p ?o ?g. }
Showing items 1 to 96 of
96
with 100 items per page.
- W2023161791 endingPage "344" @default.
- W2023161791 startingPage "339" @default.
- W2023161791 abstract "The effect of replacing the beta-lactam carbonyl oxygen in cephalosporins by sulfur on their reactivity has been investigated. The second-order rate constant for alkaline hydrolysis of the sulfur analogue is 2-fold less than that for the natural cephalosporin. The thioxo derivative of cephalexin, with an amino group in the C7 side chain, undergoes beta-lactam ring opening with intramolecular aminolysis by a reaction similar to that for cephalexin itself. However, the rate of intramolecular aminolysis for the S-analogue is 3 orders of magnitude greater than that for cephalexin. Furthermore, unlike cephalexin, intramolecular aminolysis in the S-analogue occurs up to pH 14 with no competitive hydrolysis. The rate of intermolecular aminolysis of natural cephalosporins is dominated by a second-order dependence on amine concentration, whereas that for thioxocephalosporins shows only a first-order term in amine. The Bronsted beta(nuc) for the aminolysis of thioxo-cephalosporin is +0.39, indicative of rate-limiting formation of the tetrahedral intermediate with an early transition state with relatively little C-N bond formation." @default.
- W2023161791 created "2016-06-24" @default.
- W2023161791 creator A5005904584 @default.
- W2023161791 creator A5035571076 @default.
- W2023161791 creator A5042398293 @default.
- W2023161791 creator A5062098859 @default.
- W2023161791 date "2003-12-17" @default.
- W2023161791 modified "2023-09-27" @default.
- W2023161791 title "Kinetics and Mechanisms of Hydrolysis and Aminolysis of Thioxocephalosporins" @default.
- W2023161791 cites W2009905061 @default.
- W2023161791 cites W2015380322 @default.
- W2023161791 cites W2037886649 @default.
- W2023161791 cites W2056044985 @default.
- W2023161791 cites W2163687094 @default.
- W2023161791 cites W4240309139 @default.
- W2023161791 cites W658155495 @default.
- W2023161791 doi "https://doi.org/10.1021/jo035471t" @default.
- W2023161791 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/14725445" @default.
- W2023161791 hasPublicationYear "2003" @default.
- W2023161791 type Work @default.
- W2023161791 sameAs 2023161791 @default.
- W2023161791 citedByCount "13" @default.
- W2023161791 countsByYear W20231617912012 @default.
- W2023161791 countsByYear W20231617912013 @default.
- W2023161791 countsByYear W20231617912017 @default.
- W2023161791 countsByYear W20231617912018 @default.
- W2023161791 countsByYear W20231617912020 @default.
- W2023161791 crossrefType "journal-article" @default.
- W2023161791 hasAuthorship W2023161791A5005904584 @default.
- W2023161791 hasAuthorship W2023161791A5035571076 @default.
- W2023161791 hasAuthorship W2023161791A5042398293 @default.
- W2023161791 hasAuthorship W2023161791A5062098859 @default.
- W2023161791 hasConcept C121332964 @default.
- W2023161791 hasConcept C131779359 @default.
- W2023161791 hasConcept C142724271 @default.
- W2023161791 hasConcept C148898269 @default.
- W2023161791 hasConcept C155647269 @default.
- W2023161791 hasConcept C160964918 @default.
- W2023161791 hasConcept C161790260 @default.
- W2023161791 hasConcept C178790620 @default.
- W2023161791 hasConcept C178907741 @default.
- W2023161791 hasConcept C185592680 @default.
- W2023161791 hasConcept C192604958 @default.
- W2023161791 hasConcept C204787440 @default.
- W2023161791 hasConcept C2776910235 @default.
- W2023161791 hasConcept C2777998946 @default.
- W2023161791 hasConcept C62520636 @default.
- W2023161791 hasConcept C71240020 @default.
- W2023161791 hasConcept C71924100 @default.
- W2023161791 hasConcept C75079739 @default.
- W2023161791 hasConcept C90932021 @default.
- W2023161791 hasConcept C93391505 @default.
- W2023161791 hasConcept C94412978 @default.
- W2023161791 hasConceptScore W2023161791C121332964 @default.
- W2023161791 hasConceptScore W2023161791C131779359 @default.
- W2023161791 hasConceptScore W2023161791C142724271 @default.
- W2023161791 hasConceptScore W2023161791C148898269 @default.
- W2023161791 hasConceptScore W2023161791C155647269 @default.
- W2023161791 hasConceptScore W2023161791C160964918 @default.
- W2023161791 hasConceptScore W2023161791C161790260 @default.
- W2023161791 hasConceptScore W2023161791C178790620 @default.
- W2023161791 hasConceptScore W2023161791C178907741 @default.
- W2023161791 hasConceptScore W2023161791C185592680 @default.
- W2023161791 hasConceptScore W2023161791C192604958 @default.
- W2023161791 hasConceptScore W2023161791C204787440 @default.
- W2023161791 hasConceptScore W2023161791C2776910235 @default.
- W2023161791 hasConceptScore W2023161791C2777998946 @default.
- W2023161791 hasConceptScore W2023161791C62520636 @default.
- W2023161791 hasConceptScore W2023161791C71240020 @default.
- W2023161791 hasConceptScore W2023161791C71924100 @default.
- W2023161791 hasConceptScore W2023161791C75079739 @default.
- W2023161791 hasConceptScore W2023161791C90932021 @default.
- W2023161791 hasConceptScore W2023161791C93391505 @default.
- W2023161791 hasConceptScore W2023161791C94412978 @default.
- W2023161791 hasIssue "2" @default.
- W2023161791 hasLocation W20231617911 @default.
- W2023161791 hasLocation W20231617912 @default.
- W2023161791 hasOpenAccess W2023161791 @default.
- W2023161791 hasPrimaryLocation W20231617911 @default.
- W2023161791 hasRelatedWork W1984837618 @default.
- W2023161791 hasRelatedWork W1997290755 @default.
- W2023161791 hasRelatedWork W2023325541 @default.
- W2023161791 hasRelatedWork W2024004531 @default.
- W2023161791 hasRelatedWork W2031424732 @default.
- W2023161791 hasRelatedWork W2060738414 @default.
- W2023161791 hasRelatedWork W2080189005 @default.
- W2023161791 hasRelatedWork W2094070964 @default.
- W2023161791 hasRelatedWork W2097097278 @default.
- W2023161791 hasRelatedWork W2952826063 @default.
- W2023161791 hasVolume "69" @default.
- W2023161791 isParatext "false" @default.
- W2023161791 isRetracted "false" @default.
- W2023161791 magId "2023161791" @default.
- W2023161791 workType "article" @default.