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SN2 Mechanism for Alcoholysis, Aminolysis, and Hydrolysis of Acetyl Chloride
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What this work says
Outgoing claims: the papers this work cites, builds on, or argues with.
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The Absolute Proton Affinity for Isobutene
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Y X Scales of Solvent Ionizing Power
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Substituent effects on the kinetic solvent isotope effect in solvolyses of arenesulphonyl chlorides
inferredcites →https://doi.org/10.1007/978-94-009-4099-4openalex-snapshot
Thermochemical Data of Organic Compounds
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An evaluation of the performance of density functional theory, MP2, MP4, F4, G2(MP2) and G2 procedures in predicting gas-phase proton affinities
inferredcites →https://doi.org/10.1016/0168-1176(90)87012-6openalex-snapshot
The heat of formation of the acetyl cation: a theoretical evaluation
inferredcites →https://doi.org/10.1016/s0021-9673(00)87024-7openalex-snapshot
High-performance liquid chromatography of carboxylic acids
inferredcites →https://doi.org/10.1016/s0065-3160(08)60312-3openalex-snapshot
General Base and Nucleophilic Catalysis of Ester Hydrolysis and Related Reactions
inferredcites →https://doi.org/10.1021/ja00010a040openalex-snapshot
Concerted mechanism for alcoholysis of esters: an examination of the requirements
inferredcites →https://doi.org/10.1021/ja00058a006openalex-snapshot
Structure-reactivity correlations for reactions of substituted phenolate anions with acetate and formate esters
inferredcites →https://doi.org/10.1021/ja00064a058openalex-snapshot
Assigning absolute values to proton affinities: a differentiation between competing scales
inferredcites →https://doi.org/10.1021/ja00070a033openalex-snapshot
Progress toward an absolute gas-phase proton affinity scale
inferredcites →https://doi.org/10.1021/ja00079a062openalex-snapshot
The tert-butyl ion heat of formation and the isobutene proton affinity
inferredcites →https://doi.org/10.1021/ja00092a054openalex-snapshot
Is SN2 Substitution with Inversion of Configuration at Vinylic Carbon Feasible?
inferredcites →https://doi.org/10.1021/ja00104a007openalex-snapshot
Concerted or Stepwise Mechanisms for Acyl Transfer Reactions of p-Nitrophenyl Acetate? Transition State Structures from Isotope Effects
inferredcites →https://doi.org/10.1021/ja00113a018openalex-snapshot
SN2 and AdN-E Mechanisms in Bimolecular Nucleophilic Substitutions at Vinyl Carbon. The Relevance of the LUMO Symmetry of the Electrophile
inferredcites →https://doi.org/10.1021/ja00125a008openalex-snapshot
Stepwise versus Concerted Mechanisms at Trigonal Carbon: Transfer of the 1,3,5-Triazinyl Group between Aryl Oxide Ions in Aqueous Solution
inferredcites →https://doi.org/10.1021/ja00204a021openalex-snapshot
Mechanism of solvolysis of substituted benzoyl halides
inferredcites →https://doi.org/10.1021/ja00204a022openalex-snapshot
Aminolysis of benzoyl fluorides in water
inferredcites →https://doi.org/10.1021/ja00247a007openalex-snapshot
Ab initio study of the displacement reactions of chloride ion with formyl and acetyl chloride
inferredcites →https://doi.org/10.1021/ja00255a021openalex-snapshot
Concertedness in acyl group transfer in solution: a single transition state in acetyl group transfer between phenolate ion nucleophiles
inferredcites →https://doi.org/10.1021/ja00267a030openalex-snapshot
Essentially solvent-independent rates of solvolysis of the 1-adamantyldimethylsulfonium ion. Implications regarding nucleophilic assistance in solvolyses of tert-butyl derivatives and the NKL solvent nucleophilicity scale
inferredcites →https://doi.org/10.1021/ja00293a048openalex-snapshot
Mechanism of solvolysis of 2,2-dimethylcyclopentyl p-bromobenzenesulfonate
inferredcites →https://doi.org/10.1021/ja00322a026openalex-snapshot
Perchlorate esters. 7. Solvolysis of 2-adamantyl perchlorate: rate and product studies
inferredcites →https://doi.org/10.1021/ja00329a040openalex-snapshot
Nucleophilic reactivity toward acetyl chloride in water
inferredcites →https://doi.org/10.1021/ja00335a008openalex-snapshot
Stabilization energy and ion size in carbocations in the gas phase.
inferredcites →https://doi.org/10.1021/ja00384a010openalex-snapshot
Heat of formation for acetyl cation in the gas phase
inferredcites →https://doi.org/10.1021/ja00385a031openalex-snapshot
The SN2-SN1 spectrum. 4. The SN2 (intermediate) mechanism for solvolyses of tert-butyl chloride: a revised Y scale of solvent ionizing power based on solvolyses of 1-adamantyl chloride
inferredcites →https://doi.org/10.1021/ja00398a057openalex-snapshot
Acyl transfer reactions in the gas phase. The question of tetrahedral intermediates
inferredcites →https://doi.org/10.1021/ja00408a031openalex-snapshot
The SN2-SN1 spectrum. 3. Solvolyses of secondary and tertiary alkyl sulfonates in fluorinated alcohols. Further evidence for the SN2 (intermediate) mechanism
inferredcites →https://doi.org/10.1021/ja00440a037openalex-snapshot
The SN2-SN1 spectrum. 2. Quantitative treatments of nucleophilic solvent assistance. A scale of solvent nucleophilicities
inferredcites →https://doi.org/10.1021/ja00463a033openalex-snapshot
Ester aminolysis. Partitioning of the tetrahedral addition intermediate, T.+-., and the relative leaving ability of nitrogen and oxygen
inferredcites →https://doi.org/10.1021/ja00494a020openalex-snapshot
Contrasting responses in aqueous trifluoroethanol and aqueous ethanol as a probe for nucleophilic solvent assistance in solvolysis
inferredcites →https://doi.org/10.1021/ja00508a002openalex-snapshot
Gas phase nucleophilic displacement reactions of negative ions with carbonyl compounds
inferredcites →https://doi.org/10.1021/ja00531a027openalex-snapshot
Solvolysis in 2,2,2-trifluoroethanol-water and 2,2,2-trifluoroethanol-ethanol mixtures. Selectivity of the intermediates and N values
inferredcites →https://doi.org/10.1021/ja00884a006openalex-snapshot
Acylium Ion Formation in the Reactions of Carboxylic Acid Derivatives. III. The Hydrolysis of 4-Substituted-2,6-dimethylbenzoyl Chlorides
inferredcites →https://doi.org/10.1021/ja01046a020openalex-snapshot
Acylation mechanisms in aprotic solvents. I. Methanolysis of p-nitrobenzoyl chloride in acetonitrile
inferredcites →https://doi.org/10.1021/ja01509a032openalex-snapshot
Secondary Deuterium Isotope Effects in the Reactions of Carboxylic Acid Derivatives1a
inferredcites →https://doi.org/10.1021/ja01579a027openalex-snapshot
Correlation of Solvolysis Rates. IV.1 Solvent Effects on Enthalpy and Entropy of Activation for Solvolysis of t-Butyl Chloride2
inferredcites →https://doi.org/10.1021/ja01593a033openalex-snapshot
Correlation of Solvolysis Rates. III.1 t-Butyl Chloride in a Wide Range of Solvent Mixtures2
inferredcites →https://doi.org/10.1021/ja01607a026openalex-snapshot
The Kinetics of Hydrolysis of Acetyl Chloride in Acetone-Water Mixtures
inferredcites →https://doi.org/10.1021/ja01627a059openalex-snapshot
Mechanisms of Hydrolysis of Carbonyl Chlorides1
inferredcites →https://doi.org/10.1021/jo00004a048openalex-snapshot
Distinguishing between solvation effects and mechanistic changes. Effects due to differences in solvation of aromatic rings and alkyl groups
inferredcites →https://doi.org/10.1021/jo00005a034openalex-snapshot
An improved scale of solvent nucleophilicity based on the solvolysis of the S-methyldibenzothiophenium ion
inferredcites →https://doi.org/10.1021/jo00009a018openalex-snapshot
Solvolysis of 2-aryl-2-chloroadamantanes. A new Y scale for benzylic chlorides
inferredcites →https://doi.org/10.1021/jo00034a035openalex-snapshot
Solvation effects adjacent to the reaction site. Differences in solvation between alkyl, alkenyl or alkynyl, and aryl groups in binary aqueous mixtures
inferredcites →https://doi.org/10.1021/jo00080a008openalex-snapshot
Concerted mechanism of the reactions of secondary alicyclic amines with O-ethyl S-(2,4,6-trinitrophenyl) thiocarbonate
inferredcites →https://doi.org/10.1021/jo00111a022openalex-snapshot
Kinetics and Selectivities for the Solvolysis of N,N-Diphenylcarbamoyl Chloride
inferredcites →https://doi.org/10.1021/jo00129a016openalex-snapshot
Kinetics and Mechanism of Reactions of Benzhydryl Chlorides with Anilines
inferredcites →https://doi.org/10.1021/jo00166a007openalex-snapshot
Molecular orbital study on the gas-phase nucleophilic displacement on acyl chlorides
inferredcites →https://doi.org/10.1021/jo00200a034openalex-snapshot
Solvent ionizing power - comparisons of solvolyses of 1-adamantyl chlorides, bromides, iodides, and tosylates in protic solvents
inferredcites →https://doi.org/10.1021/jo00218a017openalex-snapshot
Solvolysis of 2-adamantyl trifluoromethanesulfonate: a YOTf scale
inferredcites →https://doi.org/10.1021/jo00239a004openalex-snapshot
Separation of mass law and solvent effects in kinetics of solvolyses of p-nitrobenzoyl chloride in aqueous binary mixtures
inferredcites →https://doi.org/10.1021/jo00974a020openalex-snapshot
Nucleophilic reactivity to diphenylcarbamoyl derivatives. Unimolecular nature of diphenylcarbamoyl chloride hydrolysis
inferredcites →https://doi.org/10.1021/jo01053a032openalex-snapshot
Ion Paris. II. Kinetics and Salt Effects in the Solvolysis of Acetyl Chloride in Glacial Acetic Acid1
inferredcites →https://doi.org/10.1039/c39840000387openalex-snapshot
S N2 character of hydrolysis of benzoyl chloride
inferredcites →https://doi.org/10.1039/jr9620005157openalex-snapshot
993. The mechanism of hydrolysis of acid chlorides. Part IX. Acetyl chloride
inferredcites →https://doi.org/10.1039/jr9640002982openalex-snapshot
573. The mechanism of hydrolysis of acid chlorides. Part X. Salt effects
inferredcites →https://doi.org/10.1039/p29780000595openalex-snapshot
Reactivity–selectivity relationships. Part 7. Solvent effects on the selectivity of adamantyl derivatives in aqueous ethanol
inferredcites →https://doi.org/10.1039/p29790000646openalex-snapshot
Classical carbonium ions. Part 10. Selectivity in the solvolytic products from 1-adamantyl derivatives in aqueous ethanol
inferredcites →https://doi.org/10.1039/p29840001115openalex-snapshot
Mechanistic applications of high performance liquid chromatography. Rate–product correlations for competing solvolysis and aminolysis of benzoyl chloride
inferredcites →https://doi.org/10.1039/p29850000983openalex-snapshot
Competing S N2 and carbonyl addition pathways for solvolyses of benzoyl chloride in aqueous media
inferredcites →https://doi.org/10.1039/p29860000619openalex-snapshot
Solvolyses of para-substituted benzoyl chlorides in trifluoroethanol and in highly aqueous media
inferredcites →https://doi.org/10.1039/p29880000783openalex-snapshot
Rapid solvolyses of 2,6-dimethyl-and 2,4,6-trimethyl-benzoyl chlorides: model systems for solvent effects on the reactivity of acid chlorides
inferredcites →https://doi.org/10.1039/p29880001353openalex-snapshot
Nucleophilic substitution at trigonal carbon. Part 4. Substituent effects in the reactions of aliphatic acyl chlorides with methanol and phenol in acetonitrile
inferredcites →https://doi.org/10.1039/p29880001717openalex-snapshot
Substitution at saturated carbon. Part 26. A complete analysis of solvent effects on initial states and transition states for the solvolysis of the t-butyl halides in terms of G, H, and S using the unified method
inferredcites →https://doi.org/10.1039/p29890001055openalex-snapshot
Weakly nucleophilic leaving groups. Solvolyses of 1-adamantyl and t-butyl heptafluorobutyrates and trifluoroacetates
inferredcites →https://doi.org/10.1039/p29890001385openalex-snapshot
Trends in selectivity. Evidence from rates and products for simultaneous reaction channels in solvolyses of benzoyl chloride and substituted derivatives
inferredcites →https://doi.org/10.1039/p29910000063openalex-snapshot
Kinetics and mechanism of the aminolysis of 2,4-dinitrophenyl and 2,4,6-trinitrophenyl thiolacetates
inferredcites →https://doi.org/10.1039/p29910000175openalex-snapshot
Limitations of the transition state variation model. Part 2. Dual reaction channels for solvolyses of 2,4,6-trimethylbenzenesulphonyl chloride
inferredcites →https://doi.org/10.1039/p29910001175openalex-snapshot
Limitations of the transition-state variation model. Part 3. Solvolyses of electron-rich benzenesulphonyl chlorides
inferredcites →https://doi.org/10.1039/p29930000307openalex-snapshot
Nucleophilic substitution at a trigonal carbon. Part 5. Substituent effects in the reactions of aromatic acyl bromides with methanol in acetonitrile
inferredcites →https://doi.org/10.1039/p29930001575openalex-snapshot
Reactivity–selectivity relationship and kinetic solvent isotope effects in nucleophilic substitution reactions
inferredcites →https://doi.org/10.1039/p29930001659openalex-snapshot
Dual reaction channels for solvolyses of acyl chlorides in alcohol–water mixtures
inferredcites →https://doi.org/10.1039/p29930002351openalex-snapshot
Stoichiometric solvation effects. Part 1. New equations relating product selectivities to alcohol–water solvent compositions for hydrolyses of p-nitrobenzoyl chloride
inferredcites →https://doi.org/10.1039/p29940000753openalex-snapshot
Stoichiometric solvation effects. Part 2. A new product–rate correlation for solvolyses of p-nitrobenzenesulfonyl chloride in alcohol–water mixtures
inferredcites →https://doi.org/10.1039/p29950002263openalex-snapshot
Nucleophilic substitution reactions of phenyl chloroformates
inferredcites →https://doi.org/10.1063/1.1700893openalex-snapshot
Kinetics of the Hydrolysis of Acetyl Chloride
inferredcites →https://doi.org/10.1139/v67-264openalex-snapshot
Kinetics of the hydrolysis of acyl chlorides in pure water
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The Solvolysis of Acid Chlorides. A Presentation of the Problem and a Proposal for the Mechanism
What points at this work
Incoming claims: where this work appears in other papers’ reference lists and arguments.
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Substituent effects on the formation of sulfonyl cations from sulfonyl chlorides: comparisons of solvolysis kinetic data with calculated gas phase energies
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Concerted SN2 mechanism for the hydrolysis of acid chlorides: comparisons of reactivities calculated by the density functional theory with experimental data
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Influence of the ortho effect in the solvolyses of dichlorobenzoyl chlorides
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Correlation of the rates of solvolysis of acetic p‐toluenesulfonic anhydride (acetyl p‐toluenesulfonate) and a comparison with acetyl halides
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Extended Grunwald-Winstein Analysis - LFER Used to Gauge Solvent Effects in p-Nitrophenyl Chloroformate Solvolysis
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Marked Difference in Solvation Effects and Mechanism between Solvolyses of Substituted Acetylchloride with Alkyl Groups and with Aromatic Rigns in Aqueous Fluorinated Alcohol and in 2,2,2-Trifluoroethanol-Ethanol Solvent Systems
inferred← citeshttps://doi.org/10.5012/bkcs.2003.24.9.1293openalex-snapshot
Applications of Third Order Models in Solvolytic Reaction of Aliphatic Substituted Acyl Derivatives in 2,2,2-Trifluoroethanol-Ethanol Systems
inferred← citeshttps://doi.org/10.5012/bkcs.2012.33.6.1955openalex-snapshot
Comparative Studies on the Reactions of Carbamyl and Thiocarbamyl Halides with NH3in the Gas Phase and in Aqueous Solution: A Theoretical Study
inferred← citeshttps://doi.org/10.70675/8a49ed06zf2c2z4c59za254zab52e3eac222openalex-snapshot
Approche théorique de la réactivité des isonitriles en chimie organique
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