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Structural effects on the solvolytic reactivity of carboxylic and sulfonic acid chlorides. Comparisons with gas-phase data for cation formation.
  • T. Bentley
  • Chemistry, Medicine
  • The Journal of organic chemistry
  • 17 July 2008
Kinetic data for solvolyses of 28 acid chlorides in 97% w/w trifluoroethanol (TFE)-water spanning over 10 (9) in rate constant at 25 degrees C are obtained directly or by short extrapolation fromExpand
  • 31
  • 3
Medium Effects on the Rates and Mechanisms of Solvolytic Reactions
Publisher Summary Solvolytic reactions frequently are used to derive structure/reactivity relationships and the results are implicitly assumed to be independent of the solvent. The solvent acts as aExpand
  • 96
  • 2
Solvolytic Reactions in Fluorinated Alcohols. Role of Nucleophilic and Other Solvation Effects
Rate constants and products for solvolyses of chlorodiphenylmethane (Ph2CHCl) and p-methoxybenzyl chloride in 2,2,2-trifluoroethanol (TFE)/water and TFE/ethanol are reported, along with additionalExpand
  • 48
  • 2
Substituent effects on the formation of sulfonyl cations from sulfonyl chlorides: comparisons of solvolysis kinetic data with calculated gas phase energies
Suitable theoretical methods are validated for organosulfur compounds using experimental data for gas phase enthalpies of formation, proton affinities (PA) and heterolytic bond dissociationExpand
  • 14
  • 2
YX Scales of Solvent Ionizing Power
  • 126
  • 1
Solvation effects adjacent to the reaction site. Differences in solvation between alkyl, alkenyl or alkynyl, and aryl groups in binary aqueous mixtures
Rate constants for solvolyses of 4-chloropent-2-ene (a,y-dimethylallyl chloride, 1) and 4-chloro-4-methylpent-2-yne (2) are reported for aqueous binary mixtures with acetonitrile, acetone, dioxane,Expand
  • 51
  • 1
  • PDF
Mechanisms of solvolyses of acid chlorides and chloroformates. Chloroacetyl and phenylacetyl chloride as similarity models.
[reaction: see text] Rate constants and product selectivities (S = ([ester product]/[acid product]) x ([water]/[alcohol solvent]) are reported for solvolyses of chloroacetyl chloride (3) at -10Expand
  • 36
  • 1
Stoichiometric solvation effects. Part 1. New equations relating product selectivities to alcohol–water solvent compositions for hydrolyses of p-nitrobenzoyl chloride
Rate constants at 25 °C are reported for solvolyses of p-nitrobenzoyl chloride (1) in water, D2O, and in acetonitrile–water, ethanol–water and methanol–water mixtures, and activation parameters areExpand
  • 25
  • 1
Solvent ionizing power: comparisons of solvolyses of 1-adamantyl chlorides, bromides, iodides, and tosylates in protic solvents
Mesure des constantes de vitesse de solvolyse des composes du titre dans des melanges binaires aqueux d'ethanol, methanol, acetone, trifluoroethanol, hexafluoro isopropanol, et dans les acidesExpand
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