Kinetics of hydroxide and nitromethide ion addition to substituted .beta.-nitrostyrenes in dimethyl sulfoxide-water mixtures. Solvent dependence of .pi.-donor substituent effects and of intrinsic rate constants

Claude F. Bernasconi; Janie L. Zitomer; David F. Schuck

doi:10.1021/jo00030a019

Kinetics of hydroxide and nitromethide ion addition to substituted .beta.-nitrostyrenes in dimethyl sulfoxide-water mixtures. Solvent dependence of .pi.-donor substituent effects and of intrinsic rate constants

The Journal of Organic Chemistry ◽

10.1021/jo00030a019 ◽

1992 ◽

Vol 57 (4) ◽

pp. 1132-1139 ◽

Cited By ~ 3

Author(s):

Claude F. Bernasconi ◽

Janie L. Zitomer ◽

David F. Schuck

Keyword(s):

Dimethyl Sulfoxide ◽

Rate Constants ◽

Substituent Effects ◽

Intrinsic Rate ◽

Solvent Dependence ◽

Kinetics Of ◽

Donor Substituent

Kinetics of proton transfer of 3,5-heptanedione, 2,6-dimethyl-3,5-heptanedione, and dibenzoylmethane with amines in 50% dimethyl sulfoxide-50% water. Effect of steric crowding and .pi.-overlap on intrinsic rate constants

The Journal of Organic Chemistry ◽

10.1021/jo00009a017 ◽

1991 ◽

Vol 56 (9) ◽

pp. 3016-3020 ◽

Cited By ~ 8

Author(s):

Claude F. Bernasconi ◽

Douglas A. A. Ohlberg ◽

Michael W. Stronach

Keyword(s):

Proton Transfer ◽

Dimethyl Sulfoxide ◽

Rate Constants ◽

Intrinsic Rate ◽

Water Effect ◽

Steric Crowding ◽

Kinetics Of

ChemInform Abstract: Kinetics of Proton Transfer from 2-Nitro-4-X-phenylacetonitriles to Piperidine and Morpholine in Aqueous Me2SO. Solvent and Substituent Effects on Intrinsic Rate Constants. Transition State Imbalances.

ChemInform ◽

10.1002/chin.199711048 ◽

2010 ◽

Vol 28 (11) ◽

pp. no-no

Author(s):

C. F. BERNASCONI ◽

P. J. WENZEL

Keyword(s):

Proton Transfer ◽

Transition State ◽

Rate Constants ◽

Substituent Effects ◽

Intrinsic Rate ◽

Kinetics Of

Kinetics of deprotonation of triphenyl(2-substituted-9-fluorenyl)phosphonium ions in 50% dimethyl sulfoxide-50% water. Intrinsic rate constants, imbalances and evidence for changes in transition state structure

Journal of Physical Organic Chemistry ◽

10.1002/poc.610050705 ◽

1992 ◽

Vol 5 (7) ◽

pp. 409-423 ◽

Cited By ~ 1

Author(s):

Claude F. Bernasconi ◽

Douglas E. Fairchild

Keyword(s):

Transition State ◽

Dimethyl Sulfoxide ◽

Rate Constants ◽

Intrinsic Rate ◽

State Structure ◽

Transition State Structure ◽

Kinetics Of

Kinetics of Proton Transfer from 2-Nitro-4-X-phenylacetonitriles to Piperidine and Morpholine in Aqueous Me2SO. Solvent and Substituent Effects on Intrinsic Rate Constants. Transition State Imbalances

Journal of the American Chemical Society ◽

10.1021/ja961837q ◽

1996 ◽

Vol 118 (46) ◽

pp. 11446-11453 ◽

Cited By ~ 14

Author(s):

Claude F. Bernasconi ◽

Philip J. Wenzel

Keyword(s):

Proton Transfer ◽

Transition State ◽

Rate Constants ◽

Substituent Effects ◽

Intrinsic Rate ◽

Kinetics Of

ChemInform Abstract: Kinetics of Deprotonation of Arylnitromethanes by Benzoate Ions in Acetonitrile Solution. Effect of Equilibrium and Nonequilibrium Transition-State Solvation on Intrinsic Rate Constants of Proton Transfers

ChemInform ◽

10.1002/chin.199220042 ◽

2010 ◽

Vol 23 (20) ◽

pp. no-no

Author(s):

J. R. GANDLER ◽

C. F. BERNASCONI

Keyword(s):

Transition State ◽

Rate Constants ◽

Intrinsic Rate ◽

Acetonitrile Solution ◽

Proton Transfers ◽

Kinetics Of

ChemInform Abstract: Nucleophilic Addition to Olefins. Part 25. Kinetics of Hydrolysis of Substituted β-Nitrostyrenes. Transition-State Imbalances and Intrinsic Rate Constants for Three Different Types of Nitronate Ion Forming Processes. Relevance to the

ChemInform ◽

10.1002/chin.198944081 ◽

1989 ◽

Vol 20 (44) ◽

Author(s):

C. F. BERNASCONI ◽

P. PASCHALIS

Keyword(s):

Transition State ◽

Rate Constants ◽

Nucleophilic Addition ◽

Intrinsic Rate ◽

Kinetics Of Hydrolysis ◽

Different Types ◽

Kinetics Of ◽

Hydrolysis Of

Nucleophilic addition to olefins. 16. Unusual substituent effects in the reaction of amines with .beta.-nitrostyrenes. Solvent effect on intrinsic rate constants

Journal of the American Chemical Society ◽

10.1021/ja00275a047 ◽

1986 ◽

Vol 108 (15) ◽

pp. 4541-4549 ◽

Cited By ~ 21

Author(s):

Claude F. Bernasconi ◽

Richard A. Renfrow ◽

Paul R. Tia

Keyword(s):

Solvent Effect ◽

Rate Constants ◽

Nucleophilic Addition ◽

Substituent Effects ◽

Intrinsic Rate

ChemInform Abstract: Kinetics of Amine Addition to Benzylidene-1,3-indandione and Other Vinylic β-Diketones. Effect of Cyclic Structure and Steric Strain on Intrinsic Rate Constants.

ChemInform ◽

10.1002/chin.199129060 ◽

2010 ◽

Vol 22 (29) ◽

pp. no-no

Author(s):

C. F. BERNASCONI ◽

M. W. STRONACH

Keyword(s):

Rate Constants ◽

Intrinsic Rate ◽

Cyclic Structure ◽

Steric Strain ◽

Amine Addition ◽

Kinetics Of

Kinetics of the reaction of 5-substituted orotic acids with diazodiphenylmethane

Journal of the Serbian Chemical Society ◽

10.2298/jsc0411949j ◽

2004 ◽

Vol 69 (11) ◽

pp. 949-953 ◽

Cited By ~ 2

Author(s):

Bratislav Jovanovic ◽

Fathi Assaleh ◽

Aleksandar Marinkovic

Keyword(s):

Rate Constants ◽

Steric Effect ◽

Substituent Effects ◽

Electrical Effect ◽

Kinetics Of

Rate konstants for the reaction of eight 5-substituted orotic acids with diazodiphenylmethane (DDM) in dimethylformamide (DMF) were determined at 30 ?C by the known spectrophotometricmethod. The determined rate constants were correlated with the equations: logk2 = ??1+??R+h logk2 = ??1+??R+??+h to detect the presence and investigate the influence of both electrical and steric substituent effects. The obtained results show that the electrical effect (the localized ? field and delocalized ? resonance) is predominant and that the steric effect, althought present, is releatively small in this reaction.

Kinetics of reactions of para-substituted phenyl isocyanates with amines and alcohols

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19911662 ◽

1991 ◽

Vol 56 (8) ◽

pp. 1662-1670 ◽

Cited By ~ 1

Author(s):

Ivan Danihel ◽

Falk Barnikol ◽

Pavol Kristian

Keyword(s):

Transition State ◽

Solvent Effects ◽

Rate Constants ◽

Substituent Effects ◽

Steric Effects ◽

Stopped Flow ◽

Partial Charges ◽

Hammett Correlation ◽

One Step ◽

Kinetics Of

The reaction of para-substituted phenyl isocyanates with amines and alcohols was studied by stopped-flow method. The Hammett correlation obtained showed that the sensitivity of the above mentioned reactions toward substituent effects is the same as that of analogous reactions of phenyl isothiocyanates (ρ ~ 2). The rate constants of these reactions were found to be affected more by steric effects than by solvent effects. An one step multicentre mechanism with partial charges in transition state has been proposed for the title reactions.