Literature DB >> 22168236

Investigation of solvent effects on the rate and stereoselectivity of the Henry reaction.

Jakub Kostal1, Adelina M Voutchkova, William L Jorgensen.   

Abstract

A combined computational and experimental kinetic study on the Henry reaction is reported. The effects of solvation on the transition structures and the rates of reaction between nitromethane and formaldehyde, and between nitropropane and benzaldehyde are elucidated with QM/MM calculations.
© 2011 American Chemical Society

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Year:  2011        PMID： 22168236      PMCID： PMC3258499          DOI： 10.1021/ol2030394

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  Nitroaldol Reaction in Aqueous Media: An Important Improvement of the Henry Reaction.

Authors:  Roberto Ballini; Giovanna Bosica
Journal:  J Org Chem       Date:  1997-01-24       Impact factor: 4.354

2.  Steric retardation of SN2 reactions in the gas phase and solution.

Authors:  Grigoriy Vayner; K N Houk; William L Jorgensen; John I Brauman
Journal:  J Am Chem Soc       Date:  2004-07-28       Impact factor: 15.419

3.  Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update.

Authors:  Chao-Jun Li
Journal:  Chem Rev       Date:  2005-08       Impact factor: 60.622

4.  Solvent polarization and kinetic isotope effects in nitroethane deprotonation and implications to the nitroalkane oxidase reaction.

Authors:  Dan T Major; Darrin M York; Jiali Gao
Journal:  J Am Chem Soc       Date:  2005-11-30       Impact factor: 15.419

5.  'Green' synthesis of nitro alcohols catalyzed by solid-supported tributylammonium chloride in aqueous medium.

Authors:  Zongting Wang; Huiqing Xue; Shuchao Wang; Cunguang Yuan
Journal:  Chem Biodivers       Date:  2005-09       Impact factor: 2.408

6.  Comparison of nitroaldol reaction mechanisms using accurate ab initio calculations.

Authors:  Deborah Zorn; Victor S-Y Lin; Marek Pruski; Mark S Gordon
Journal:  J Phys Chem A       Date:  2008-09-30       Impact factor: 2.781

7.  Advances in quantum and molecular mechanical (QM/MM) simulations for organic and enzymatic reactions.

Authors:  Orlando Acevedo; William L Jorgensen
Journal:  Acc Chem Res       Date:  2010-01-19       Impact factor: 22.384
  7 in total
  4 in total

1.  Application of a BOSS-Gaussian interface for QM/MM simulations of Henry and methyl transfer reactions.

Authors:  Jonah Z Vilseck; Jakub Kostal; Julian Tirado-Rives; William L Jorgensen
Journal:  J Comput Chem       Date:  2015-08-27       Impact factor: 3.376

2.  DFT study of the dual catalytic role of L-proline in the aldol reaction and the effect of water on it.

Authors:  Yasaman Nobakht; Nematollah Arshadi
Journal:  J Mol Model       Date:  2018-11-06       Impact factor: 1.810

3.  Quantum and Molecular Mechanical (QM/MM) Monte Carlo Techniques for Modeling Condensed-Phase Reactions.

Authors:  Orlando Acevedo; Wiliiam L Jorgensen
Journal:  Wiley Interdiscip Rev Comput Mol Sci       Date:  2014-09

4.  Effects of solvents on the DACBO-catalyzed vinylogous Henry reaction of isatin with 3,5-dimethyl-4-nitroisoxazole "on-water" and in solution from QM/MM MC simulations.

Authors:  Lian Yang; Jianming Zhao; Xin Yang; Ming Chen; Ying Xue
Journal:  RSC Adv       Date:  2019-02-08       Impact factor: 4.036
  4 in total

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